Title:
Glycopeptide antibiotics
Kind Code:
A1


Abstract:
The invention provides compounds of formula embedded image
Wherein R1, R2, R3, R4, R5, R6a, R6b, R6c, R6d, R6e and R7 are defined in the specification. These compounds are useful as antibiotic agents.



Inventors:
Lotvin, Jason Arnold (Union, NJ, US)
Ruppen, Mark Edward (Garnerville, NY, US)
Application Number:
11/116149
Publication Date:
12/29/2005
Filing Date:
04/27/2005
Assignee:
Wyeth Holdings Corporation (Madison, NJ, US)
Primary Class:
Other Classes:
514/21.1, 530/317, 514/3.1
International Classes:
C07H15/203; C07H19/04; C07K9/00; C12P19/28; (IPC1-7): A61K38/12; C07K7/64
View Patent Images:



Primary Examiner:
LILLING, HERBERT J
Attorney, Agent or Firm:
Pfizer Inc. (Attn:Legal Patent Department, Chief IP Counsel 235 East 42nd Street, New York, NY, 10017, US)
Claims:
1. 1-88. (canceled)

89. A microorganism Streptomyces hygroscopicus LL4600, or a mutant thereof.

90. A microorganism Streptomyces hygroscopicus LL4614, or a mutant thereof.

91. A microorganism Streptomyces hygroscopicus LL4666, or a mutant thereof.

92. A microorganism Streptomyces hygroscopicus LL4690, or a mutant thereof.

93. A microorganism Streptomyces hygroscopicus LL4728, or a mutant thereof.

94. A microorganism Streptomyces hygroscopicus LL4741, or a mutant thereof.

95. A microorganism Streptomyces hygroscopicus LL4742, or a mutant thereof.

96. A microorganism Streptomyces hygroscopicus LL4744, or a mutant thereof.

97. A microorganism Streptomyces hygroscopicus LL4773, or a mutant thereof.

98. A microorganism Streptomyces hygroscopicus LL4779, or a mutant thereof.

99. A microorganism Streptomyces hygroscopicus LL4780, or a mutant thereof.

100. A microorganism Streptomyces hygroscopicus LL4783, or a mutant thereof.

101. A microorganism Streptomyces hygroscopicus LL4902, or a mutant thereof.

102. A microorganism Streptomyces hygroscopicus BD2, or a mutant thereof.

103. A microorganism Streptomyces hygroscopicus BD20, or a mutant thereof.

104. A microorganism Streptomyces hygroscopicus BD70, or a mutant thereof.

105. (canceled)

Description:

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims priority from copending provisional application Ser. No. 60/286,396 filed on Apr. 25, 2001, copending provisional application Ser. No. 60/286,249 filed on Apr. 25, 2001 and copending provisional application Ser. No. 60/286,244 filed on Apr. 25, 2001 all incorporated herein by reference.

FIELD OF THE INVENTION

The present invention relates to novel glycopeptides, which are,useful as antibiotics.

BACKGROUND OF THE INVENTION

New improved antibiotics are continually in demand, for the treatment of human diseases. Antibiotic resistant organisms are continually a problem, particularly in hospitals. Vancomycin has been the last defense. However, especially in hospitals, isolates which are vancomycin resistant are becoming more common. A recent survey found 7.9% of Enterococci in United States hospitals are now vancomycin resistant. “Nosocomial Enterococci Resistant to Vancomycin” Morbidity and Mortality Weekly Report 42(30):597-598(1993). Further resistance of Vancomycin and other antibiotics to Enterococcus faecium is reported, Handwergers. et al., Clin. Infect. Dis. 1993(16),750-755. Additional resistance to enterococci is reported, Boyle, J F, Clin. Microbiol. 1993(31),1280-1285. Vancomycin resistance has been reported against Staphylococcus aureus, F. A. Waldvogel, The New England Journal of Medicine, 340(7), 1999. Additional reports include: Murry, B. E. The New England Journal of Medicine, 342(10), 710-721(2000) and Y. Cetinkaya et al, Clinical Microbiology Reviews, 13(4) 686-707(2000). Clearly, antibiotic resistance is a growing public health problem. Having new antibiotics available could provide additional options for physicians in treatment regimens.

The search for new antibiotics which exhibit improved antibacterial activity against vancomycin-resistant isolates and having structures which are not derivatives of vancomycin are particularly appealing targets for screening and synthetic efforts. Structural similarity to existing antibiotics could facilitate the emergence of resistance.

The AC98-antibiotic complex isolated as an unseparated mixture of compounds of undetermined structure produced from cultures of Streptomyces hygroscopicus (strain NRRL 3085) is described in U.S. Pat. No. 3,495,004. It is an object of this invention to provide a novel family of glycopeptide antibiotics which are shown to possess antibacterial activity, especially against vancomycin resistant bacterial isolates and in particular having chemical structures unlike vancomycin.

SUMMARY OF THE INVENTION

This invention is concerned with novel glycopeptides which have antibacterial activity; with methods of treating infectious disease in mammals employing these novel glycopeptides; with pharmaceutical preparations containing these glycopeptides and processes for the production of glycopeptides of the invention. More particularly, this invention is concerned with glycopeptides which have enhanced antibacterial activity against vancomycin, penicillin and methicillin resistant strains. Compounds according to the invention comprise compounds of the formula: embedded image

    • wherein:
    • R1 is a moiety selected from: embedded image
    • R1a is H or halogen;
    • R2 is a moiety selected from: embedded image
    • provided when R2 is selected from the moieties: embedded image
    • that R1 is selected from the moieties: embedded image
    • R2a is selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), the group —C(O)—Y-Z, and a moiety selected from: embedded image
    • Y is selected from a single bond, —O— and —NR8a—;
    • Z is selected from alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl and heteroaryl;
    • and when Y is a single bond then Z is also selected from H, alkenyl(C2-C20) and alkynyl (C2-C20);
    • R2b and R2c are independently selected from H, halogen, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), aryl, heteroaryl, —NH2, —NR2fR2g, and —NO2, provided when R2b is —NO2, that R2c must be H;
    • R2d is selected from alkyl (C1-C20), alkenyl(C2-C20), alkynyl(C2-C20), aryl, heteroaryl, and when R2 is embedded image
    • R2d may also be the group L-M, wherein;
    • L is selected from —NH—, —S—, —SCH2C(O)—, and a group of the formula: embedded image
    • M is selected from alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) and alkynyl(C3-C20);
    • and when:
    • a) L is not —S—, M may also be aryl or heteroaryl;
    • b) L is —SCH2C(O)—, M may also be H, alkenyl(C2-C20) or alkynyl(C2-C20); or
    • c) L is —NH— or a group of the formula: embedded image
    • M may also be a moiety of the formula: embedded image
    • z is an integer of 1 or 2;
    • R2i, R2j and R2k are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), acyl, —Si(alkyl(C1-C20))3, —Si(alkyl(C1-C20))2(aryl), —Si(alkyl(C1-C20))(aryl)2, —Si(aryl)3, and aroyl;
    • R is S or O;
    • R2f is selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20). alkynyl(C3-C20), aryl and heteroaryl;
    • R2g is H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl and heteroaryl, and the group D-E-G, wherein;
    • D is selected from —C(O)—, —C(S)— and —S(O)2—;
    • E is selected from a single bond, and, when D is —C(O)— or —C(S)—, E is also selected from —O— and —NR2h;
    • G is selected from alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl and heteroaryl;
    • and when:
    • a) E is a single bond, then G may also be alkenyl(C2-C20) or alkynyl(C2-C20); or
    • b) D is —C(O)— or —C(S)— and E is a single bond, then G may also be H;
    • R2f and R2g may optionally when taken together with the nitrogen atom to which each is attached form a monocyclic ring having three to seven atoms independently selected from the elements C, N, O and S where said monocyclic ring optionally contains up to three nitrogen atoms, up to two oxygen atoms and up to two sulfur atoms provided said monocyclic ring does not contain —O—O—, —S—S— or —S—O— bonds;
    • R2h is selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl and heteroaryl;
    • R2h and G may optionally when taken together with the nitrogen atom to which each is attached form a monocyclic ring having three to seven atoms independently selected from the elements C, N, O and S where said monocyclic ring optionally contains up to three nitrogen atoms, up to two oxygen atoms and up to two sulfur atoms provided said monocyclic ring does not contain —O—O—, —S—S— or —S—O— bonds;
    • R3 and R4 are independently H, OH, —Si(alkyl(C1-C20))3, —Si(alkyl(C1-C20))2(aryl), —Si(alkyl(C1-C20))(aryl)2, —Si(aryl)3 or the group —C(O)—Y-Z;
    • R5 is selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), the group —C(O)—Y-Z and moieties of the formulae; embedded image
    • R6a, R6b, R6c, R6d and R6e are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), the group —C(O)—Y-Z and moieties of the formulae; embedded image
    • R6f is selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl, heteroaryl, halogen, hydroxy, alkoxy(C1-C20), aryloxy, amino, monoalkyl(C1-C20)amino, dialkyl(C1-C20)amino, carboxy, carboxyalkyl(C1-C20), carboxyaryl and carboxyamido;
    • R7 is selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), —Si(alkyl(C1-C20))3, —Si(alkyl(C1-C20))2(aryl), —Si(alkyl(C1-C20))(aryl)2, —Si(aryl)3 and the group —C(O)—Y-Z;
    • R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), —Si(alkyl(C1-C20))3, —Si(alkyl(C1-C20))2(aryl), —Si(alkyl(C1-C20))(aryl)2, —Si(aryl)3 and the group —C(O)—Y-Z or, optionally, R8 and R9, R9 and R10, R10 and R11, R13 and R14, R15 and R16, R16 and R17, R17 and R18, R19 and R20, R20 and R21 or R21 and R22 may independently be taken together forming moieties of the formulae: embedded image
    • provided when;
    • a) R8 and R9 are so joined, R9 and R10 may not be so joined;
    • b) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;
    • c) R15 and R16 are so joined, R16 and R17 may not be so joined;
    • d) R16 and R17 are so joined, R15 and R16, and R17 and R18 may not be so joined;
    • e) R19 and R20 are so joined, R20 and R21 may not be so joined;
    • f) R20 and R21 are so joined, R19 and R20, and R21 and R22 may not be so joined;
    • R8a is selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl and heteroaryl;
    • R8a and Z may optionally when taken together with the nitrogen atom to which each is attached form a monocyclic ring having three to seven atoms independently selected from the elements C, N, O and S where said monocyclic ring optionally contains up to three nitrogen atoms, up to two oxygen atoms and up to two sulfur atoms provided said monocyclic ring does not contain —O—O—, —S—S— or —S—O— bonds;
    • R23 and R24 are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), aryl, and heteroaryl;
    • R23 and R24 may optionally when taken together with the carbon atom to which each is attached form carbocyclic, monocyclic, fused, bridged, spirocyclic or polycyclic rings from three to twenty ring atoms optionally selected from the elements C, N, O and S where said monocyclic ring optionally contains up to three nitrogen atoms, up to two oxygen atoms and up to two sulfur atoms provided said monocyclic ring does not contain —O—O—, —S—S— or —S—O— bonds;
    • provided when:
    • R1 is embedded image
    • R3 and R4 are —OH;
    • R5 is embedded image
    • R2b, R2c, R6a, R6b, R6c, R6d, R6e, R7, are H;
    • that:
    • R2a is not H or moieties selected from the formulae: embedded image
    • or a pharmaceutically acceptable salt thereof.

Among the preferred groups of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroups below, wherein other variables are as defined above:

    • a)
      • R1 is a moiety selected from the group: embedded image
    • b)
      • R1 is a moiety of the formula: embedded image
    • c)
      • R1 is a moiety selected from the group: embedded image
    • d)
      • R1 is a moiety selected from the group: embedded image
    • e)
      • R1 is a moiety selected from the group: embedded image

Also among the preferred groups of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroups below, wherein other variables are as defined above:

    • a)
      • R2 is a moiety of the formula: embedded image
    • b)
      • R2 is a moiety of the formula: embedded image
      • R2b is selected from —NH2, and —NR2fR2g, and
      • R2C is H;
    • c)
      • R2 is a moiety of the formula: embedded image
      • R2a is H;
      • R2b is selected from —NH2, and —NR2fR2g; and
      • R2c is H;
    • d)
      • R2 is a moiety of the formula: embedded image
      • R2b and R2c are independently selected from H, halogen, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), aryl and heteroaryl;
    • e)
      • R2 is a moiety of the formula: embedded image
      • R2b and R2c are independently selected from H and halogen;
    • f)
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are independently selected from H and halogen;
    • g)
      • R2 is a moiety selected from the group: embedded image
    • h)
      • R2 is a moiety of the formula: embedded image
    • i)
      • R2 is a moiety selected from the group: embedded image

Additionally preferred groups of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroups below, wherein other variables are as defined above:

    • a)
      • R3 and R4 are independently selected from H and OH; or
    • b)
      • R3 and R4 are OH.

Another preferred group of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroup below, wherein other variables are as defined above:

    • R5 is selected from H or a moiety of the formula: embedded image

Also among the preferred groups of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroups below, wherein other variables are as defined above:

    • a)
      • R6a, R6b, R6c, R6d and R6e are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) and alkynyl(C3-C20);
    • b)
      • R6a, R6b, R6c, R6d and R6e are independently selected from H and moieties of the formulae: embedded image
    • c)
      • R6a, R6b, R6c, R6d and R6e are H.

Preferred groups of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroups below, wherein other variables are as defined above:

    • a)
      • R7 is H; and/or
    • b)
      • R7 is —C(O)—Y-Z; and/or
    • c)
      • R7 is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) and alkynyl(C3-C20).

Also among the preferred groups of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroups below, wherein other variables are as defined above:

    • a)
      • R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are independently selected from H and —C(O)—Y-Z;
    • b)
      • R13, R14, R19, R20, R21 and R22 are H;
      • R8, R9, R10, R11, R12, R15, R16, R17 and R18 are independently selected from H and —C(O)—Y-Z;
    • c)
      • R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) and alkynyl(C3-C20);
    • d)
      • R13, R14, R19, R20, R21 and R22 are H;
      • R8, R9, R10, R11, R12, R15, R16, R17 and R18 are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) and alkynyl(C3-C20);
    • e)
      • R8 and R9, R9and R10, R10 and R11, R13 and R14, R15 and R16, R16 and R17, R17 and R18, R19 and R20, R20 and R21 or R21 and R22 may independently be joined forming a moiety of the formula: embedded image
    • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R10 and R11and R8 and R9 may not be so joined;
      • iii) R15 and R16 are so joined, R16 and R17 may not be so joined;
      • iv) R16 and R17 are so joined, R15 and R16 and R17 and R18 may not be so joined;
      • v) R19 and R20 are so joined, R20 and R21 may not be so joined;
      • vi) R20 and R21 are so joined, R19 and R20 and R21 and R22 may not be so joined;
    • f)
      • R12, R13, R14, R19, R20, R21, and R22 are H;
      • R8 and R9, R9 and R10, R10 and R11, R15 and R16, R16 and R17 or R17 and R18 may independently be joined forming a moiety of the formula: embedded image
    • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;
      • iii) R15 and R16 are so joined, R16 and R17 may not be so joined;
      • iv) R16 and R17 are so joined, R15 and R16 and R17 and R18 may not be so joined;
    • g)
      • R8 and R9, R9 and R10, R10 and R11, R13 and R14, R15 and R16, R16 and R17, R17 and R18, R19 and R20, R20 and R21 or R21 and R22 may independently be joined forming a moiety of the formula: embedded image
    • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;
      • iii) R15 and R16 are so joined, R16 and R17 may not be so joined;
      • iv) R16 and R17 are so joined, R15 and R16 and R17 and R18 may not be so joined;
      • v) R19 and R20 are so joined, R20 and R21 may not be so joined;
      • vi) R20 and R21 are so joined, R19 and R20 and R21 and R22 may not be so joined;
    • h)
      • R12, R13, R14, R19, R20, R21, and R22 are H;
      • R8 and R9, R9 and R10, R10 and R11, R15 and R16, R16 and R17 or R17 and R18 may independently be joined forming a moiety of the formula: embedded image
    • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;
      • iii) R15 and R16 are so joined, R16 and R17 may not be so joined;
      • iv) R16 and R17 are so joined, R15 and R16 and R17 and R18 may not be so joined;
      • and
    • i)
      • R12 , R13, R14, R15, R16, R17, R18, R19, R20, R21, and R22 are H;
    • R8 and R9, R9 and R10 or R10 and R11 may independently be joined forming a moiety of the formula: embedded image
    • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;

Among the most preferred groups of compounds of this invention including pharmaceutically acceptable salts thereof are those in the subgroups below, wherein other variables are as defined above:

    • a)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7 is H;
      • R13, R14, R19, R20, R21 and R22 are H; and
      • R8, R9, R10, R11, R12, R15, R16, R17 and R18 are independently selected from H and —C(O)—Y-Z;
    • b)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7 is H;
      • R13, R14, R19, R20, R21 and R22 are H; and
      • R8, R9, R10, R11, R12, R15, R16, R17 and R18 are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) and alkynyl(C3-C20);
    • c)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7 is H;
      • R12, R13, R14, R19, R20, R21 an R22 are H;
      • R8and R9, R9 and R10, R10 and R11, R11 and R16, R16 and R17 or R17 and R18 may independently be joined forming a moiety of the formula: embedded image
      • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 may not be so joined;
      • iii) R15 and R16 are so joined, R16 and R17 may not be so joined;
      • iv) R16 and R17 are so joined, R15 and R16 and R17 and R18 may not be so joined;
    • d)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7 is H;
      • R12, R13, R14, R19, R20, R21, and R22 are H;
      • R8 and R9, R9 and R10 or R10 and R11 may independently be joined forming a moiety of the formula: embedded image
      • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8and R9 and R10 and R11 may not be so joined;
    • e)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R3 and R4 are independently H or OH;
      • R5 is H or a moiety of the formula: embedded image
      • R19, R20 R21 and R22 are H;
    • f)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d, and R6e are H;
      • R7 is H;
      • R13, R14, R19, R20, R21 and R22 are H; and
      • R8, R9, R10, R11, R12, R15, R16, R17 and R18 are independently selected from H and —C(O)—Y-Z;
    • g)
      • R1 is a moiety selected from the group: embedded image
      • R2is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7 is H;
      • R13, R14, R19, R20, R21 and R22 are H; and
      • R8, R9, R10, R11, R12, R15, R16, R17 and R18 are independently selected from H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) and alkynyl(C3-C20);
    • h)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7is H;
      • R12, R13, R14, R19, R20, R21 and R22 are H;
      • R8 and R9, R9 and R10, R10 and R11, R15 and R16, R16 and R17 or R17 and R18 may independently be joined forming a moiety of the formula: embedded image
      • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;
      • iii) R15 and R16 are so joined, R16 and R17 may not be so joined;
      • iv) R16 and R17 are so joined, R15 and R16 and R17 and R18 may not be so joined;
    • i)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7 is H;
      • R12, R13, R14, R19, R20, R21, and R22 are H;
      • R8 and R9, R9 and R10 or R10 and R11 may independently be joined forming a moiety of the formula: embedded image
      • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined,
    • i)
      • R1 is a moiety selected from the group: embedded image
      • R2is a moiety of the formula: embedded image
      • R2a is a moiety of the formula: embedded image
      • R2b and R2c are H;
      • R3 and R4 are independently H or OH;
      • R5 is a moiety of the formula: embedded image
      • R6a, R6b, R6c, R6d and R6e are H;
      • R7 is H;
      • R12, R13, R14, R19, R20, R21, and R22 are H;
      • R8 and R9, R9 and R10 or R10 and R11 may independently be joined forming a moiety of the formula: embedded image
      • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;
    • R23 and R24 when taken together with the carbon atom to which each is attached may optionally form carbocyclic, monocyclic, fused, bridged, spirocyclic or polycyclic rings of from three to twenty ring atoms;
      • provided when;
      • i) R8 and R9 are so joined, R9 and R10 may not be so joined;
      • ii) R9 and R10 are so joined, R8 and R9 and R10 and R11 may not be so joined;
    • k)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R3 and R4 are independently H or OH;
      • R5 is H or a moiety of the formula: embedded image
      • R19, R20, R21 and R22 are H;
    • and
    • l)
      • R1 is a moiety selected from the group: embedded image
      • R2 is a moiety of the formula: embedded image
      • R3 and R4 are independently H or OH;
      • R5 is H or a moiety of the formula: embedded image
      • R19, R20, R21 and R22 are H.

Specifically preferred compounds of the invention are the following compounds or a pharmaceutically acceptable salt thereof:

    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-bromo-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-sery l-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3 -bromo-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-bromo-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3α-mannopyranosylimidazolidin-4-y l)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3 -bromotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3,5-dibromo-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3α-mannopyranosylimidazolidin -4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3,5-dibromotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylsery l];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3,5-dibromo-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)-D-seryl-L-s eryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3,5-dibromotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-iodo-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3α-mannopyranosylimidazolidin-4-yl )-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-iodotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-iodo-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl -3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)-3-iodo-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-i minoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3,5-diiodo-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-s eryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)-3,5-diiodo-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-nitro-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3α-mannopyranosylimidazolidin-4-y l)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-nitrotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-nitro-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)-D-seryl-L-seryl ];
    • Cyclo[glycyl-β-methylphenylalanyl-3-nitrotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-3-nitro-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-3-nitrotyrosyl] ;
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-amino-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3α-mannopyranosylimidazolidin-4-y l)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-(dimethylamino)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimi dazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-(dimethylamino)tyrosyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)se rylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-acetamido-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazoli din-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-acetamidotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylsery l];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-(propanamido)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimida zolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-(propanamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryl seryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-(2-methylpropanamido)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyrano sylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-(2-methylpropanamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4- yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-(heptanamido)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimida zolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-(heptanamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryl seryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-(benzamido)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazo lidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-(benzamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylse ryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-formamido-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazoli din-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-formamidotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylsery l];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-[[(4-methylphenoxy)carbonyl]amino]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α- D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-[[(4-methylphenoxy)carbonyl]amino]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoim idazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-[(methoxycarbonyl)amino]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyr anosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-[(methoxycarbonyl)amino]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin -4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-[(phenylmethoxycarbonyl)amino]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-ma nnopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-[(phenylmethoxycarbonyl)amino]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidaz olidin-4-yl)serylseryl];
    • Cyclo[3-(2,3-dihydro-2-oxo-1,3-benzoxazol-5-yl)-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4- yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-(2,3-dihydro-2-oxo-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylser ylglycyl-β-methylphenylalanyl];
    • Cyclo[3-(2,3-dihydro-2-thio-1,3-benzoxazol-5-yl)-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4 -yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-(2,3-dihydro-2-thio-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylse rylglycyl-β-methylphenylalanyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-[[[3,5-bis(trifluoromethyl)phenyl]carbamothioyl]-amino]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L- seryl-3-(2-imino-3-α-D-mannopyranosyl-imidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-[[[3,5-bis(trifluoromethyl)phenyl]carbamothioyl]amino]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[3-[2-(4-carboxyphenyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin- 4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(4-carboxyphenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryls erylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-(3-nitrophenyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4- yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(3-nitrophenyl)-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylser ylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-(4-bromophenyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4- yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(4-bromophenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-methylphenylalanyl];
    • Cyclo[3-[2-[3-(4-methylphenoxy)phenyl]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimi dazolidin-4-yl)-D-seryl-L-serylglycyl-(S)- β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[3-(4-methylphenoxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin4- yl)serylserylglycyl-β-methylphenyl-alanyl];
    • Cyclo[3-[2-[4-(dimethylamino)phenyl]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[4-(dimethylamino)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4- yl)serylserylglycyl-β-methylphenyl-alanyl];
    • Cyclo[3-[2-(3-fluorophenyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(3-fluorophenyl)-1,3-benzoxazol-5-yl]alanyl3-(2-iminoimidazolidin-4-methylphenylalanyl];
    • Cyclo[3-[2-[4-(phenylmethoxy)phenyl]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimida zolidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[4-(phenylmethoxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-y l)serylserylglycyl-β-methyl-phenylalanyl];
    • Cyclo[3-[2-(4-tert-butylphenyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolid in-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(4-tert-butylphenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)ser ylserylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-([1,1-biphenyl]-4-yl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazoli din-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-([1,1-biphenyl]-4-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)s erylserylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidaz olidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl )serylserylglycyl-β-methylphenyl-alanyl];
    • Cyclo[3-[2-[3-(4-methoxyphenoxy)phenyl]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylim idazolidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[3-(4-methoxyphenoxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl-β-methylphenyl-alanyl];
    • Cyclo[3-[2-[2-α-D-glucopyranosyloxy)phenyl]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranos ylimidazolidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[2-(hexopyranosyloxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl-β-methyl-phenylalanyl];
    • Cyclo[3-[2-(9H-fluroren-2-yl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin -4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(9H-fluoren-2-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryls erylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-(3-furyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D- seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(3-furyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglyc yl-β-methylphenylalanyl];
    • Cyclo[3-[2-(2,2-diphenylethenyl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazoli din-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(2,2-diphenylethenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)se rylserylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-(2-methylprop-1-en-1-yl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidaz olidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(2-methylprop-1-en-1-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl )serylserylglycyl-β-methylphenyl-alanyl];
    • Cyclo[3-[2-[3-(4-methylphenoxy)phenyl]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)-D-ser yl-L-serylglycyl-(S)-β-methyl-L-phenyl-alanyl];
    • Cyclo[3-[2-[4-(3-methylphenoxy)phenyl]benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(2-iminoimidazolidin-4-yl)serylserylglycyl -β-methylphenylalanyl];
    • Cyclo[3-[2-(9H-fluoren-2-yl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin -4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(9H-fluoren-2-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)alany lserylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-(6-methoxynaphth-2-yl)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazol idin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(6-methoxynaphth-2-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)s erylserylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[[2-(2,3,4,6-tetra-O-benzoyl-glucopyranosyl)amino]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α -D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl-(S)-P-methyl-L-phenylalanyl];
    • Cyclo[3-[[2-(2,3,4,6-tetra-O-benzoylhexopyranosyl)amino]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-i minoimidazolidin-4-yl)seryl-serylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-(benzylthio)-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl) -D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-(benzylthio)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylg lycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-[(2-naphthylmethyl)thio]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidaz olidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[(naphthylmethyl)thio]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl) serylserylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-[(4-phenylbenzyl)thio]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazol idin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[(4-phenylbenzyl)thio]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)s erylserylglycyl-β-methylphenylalanyl];
    • Cyclo[3-[2-[(2-oxo-2-phenylethyl)thio]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimi dazolidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[(2-oxo-2-phenylethyl)thio]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl-β-methylphenyl-alanyl];
    • Cyclo[3-[2-[[2-(4-chlorophenyl)-2-oxoethyl]thio]-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopy ranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo[3-[2-[[2-(4-chlorophenyl)-2-oxoethyl]thio]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylserylglycyl-β-methylphenylalanyl];
    • Cyclo [3-cyclohexyl-L-alanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopy ranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl];
    • Cyclo[(3S)-3-cyclohexyl-L-2-aminobutanoyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2- imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexyl-2-aminobutanoyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimi dazolidin-4-yl)-serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-3-cyclohexyl-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-s eryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-3-[4-[(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)oxylcyclohexyl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3 -(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-3-[4-[(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)oxy]cyclohexyl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3 -(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[3-cyclohexyl-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl-(3S )-3-cyclohexyl-L-2-aminobutanoyl]
    • Cyclo[3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cyclohexyl-2-amino butanoyl];
    • Cyclo[3-[4-[(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)oxy]cyclohexyl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannop yranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl-(3S)-3-cyclohexyl-L-2-aminobutanoyl];
    • Cyclo[3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4 -yl)serylserylglycyl-3-cyclohexyl-2-aminobutanoyl];
    • Cyclo[3-(syn-4-hydroxycyclohexyl)-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L- serylglycyl-(3S)-3-cyclohexyl-L-2-aminobutanoyl];
    • Cyclo[3-(syn-4-hydroxycyclohexyl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cyc lohexyl-2-aminobutanoyl];
    • Cyclo[3-(anti-4-hydroxycyclohexyl)-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L- serylglycyl-(3S)-3-cyclohexyl-L-2-aminobutanoyl];
    • Cyclo[3-(anti-4-hydroxycyclohexyl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cy clohexyl-2-aminobutanoyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D- seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl ];
    • Cyclo[glycylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-cyclohexyl-L-alanyl-3-cyclohexyl-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)-serylserylglycyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[1-b enzyl-2-imino-3-α-D-mannopyranosyl-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-(2-iminoimidazolidin-4-yl)seryl-3-[1-benzyl-3-hexopyranosyl-2-im inoimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[1-( 4-tert-butylbenzyl)-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-(2-iminoimidazolidin-4-yl)seryl-3-[1-(4-tert-butylbenzyl)-3-hexo pyranosyl-2-iminoimidazolidin-4-yl]-serylseryl];
    • Di-N-(4-tert-butylbenzyl)-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Di-N-(4-tert-butylbenzyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[1-( 12-hydroxydodecyl)-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-hexopyranosyl-1-(1 2-hydroxydodecyl)-2-iminoimidazolidin-4-yl]-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-[1,3-dibenzyl-2-(benzylimino)imidazolidin -4-yl]-L-seryl-3-[1-benzyl-2-(benzyl-imino)-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[1,3-dibenzyl-2-(benzylimino)imidazolidin-4-yl]seryl-3-1-benzy l-2-(benzylimino)-3-hexopyranosylimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[1-b utyl-2-imino-3-α-D-mannopyranosyl-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-butyl-3-hexopyranosyl-2-i minoimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-[1,3-dimethyl-2-(methylimino)imidazolidin -4-yl]-L-seryl-3-[3-α-D-mannopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]-D-seryl-L-seryl]bis-methidodide
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(1,3-dimethyl-2-(methylimino)imidazolidin-4-yl)seryl-3-[3-hexo pyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]serylseryl]bis-methiodide
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-i mino-3-α-D-mannopyranosyl-1-(2-phenylbenzyl)-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino-1- (2-phenylbenzyl)-imidazolidin-4-yl]-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3- [3-(4-phenylbenzyl)-2- [(4-phenylbenzyl)imino]imidazolidin-4-yl]-L-seryl-3-[2-imino-3-α-D-mannopyranosyl-1-(4-phenylbenzyl)-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[3-(4-phenylbenzyl)-2-[(4-phenylbenzyl)iminoimidazolidin-4-yl] seryl-3-[3-hexopyranosyl-2-imino-1-(4-phenylbenzyl)-imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-i mino-3-α-D-mannopyranosyl-1-(4-phenylbenzyl)-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino-1- (4-phenylbenzyl)-imidazolidin-4-yl]-serylseryl);
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-i mino-3-α-D-mannopyranosyl-1-(2-naphthylmethyl)-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-hexopyranosyl-2-imino-1-( 2-naphthylmethyl)-imidazolidin-4-yl]-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-i mino-3-α-D-mannopyranosyl-1-(4-trifluoromethylbenzyl)-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino-1- (4-trifluoromethylbenzyl)-imidazolidin-4-yl]-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[1-( 4-carboxybenzyl)-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-(4-carboxybenzyl)-2-imino -3-hexopyranosylimidazolidin-4-yl]-serylseryl);
    • Di-N-(4-carboxybenzyl)-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-(-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolid in-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Di-N-(4-carboxybenzyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Tri-N-(4-carboxybenzyl)-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazoli din-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl]
    • Tri-N-(4-carboxybenzyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-i mino-3-α-D-mannopyranosyl-1-(3-methyl-but-2-enyl)-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-hexopyranosyl-2-imino-1-( 3-methyl-but-2-enyl)imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[1-h eptyl-2-imino-3-α-D-mannopyranosyl-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-heptyl-3-hexopyranosyl-2- iminoimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3- [1-(10-carboxydecyl)-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-(10-carboxydecyl)-3-hexop yranosyl-2-iminoimidazolidin-4-yl]serylseryl];
    • Di-N-(10-carboxydecyl)-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolid in-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Di-N-(10-carboxydecyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-[1,3-dibenzyl-2-(benzylimino)imidazolidin-4-yl]-L-alanyl-3-[1-benzyl-2-(benzylimino)-3-α-D-mannopyranosylimidazolidin-4-yl]-D-alanyl -L-serylglycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl];
    • Cyclo[3-[1,3-benzyl-2-(benzylimino)imidazolidin-4-yl]alanyl-3-[1-benzyl-2-(benzylimino)-3-hexopyranosylimidazolidin-4-yl]alanylserylglycyl-β -methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl];
    • Cyclo[3-[1,3-dimethyl-2-(methylimino)imidazolidin-4-yl]-L-alanyl-3-[3-α-D-mannopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]-D-alanyl -L-serylglycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl]bis-methiodide
    • Cyclo[3-[1,3-dimethyl-2-(methylimino)imidazolidin-4-yl alanyl-3-[3-hexopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl )tyrosyl]bis-methiodide
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-methyl-D-tyrosyl-3-[1,3-dimethyl-2-(methylimino)imidazolidin-4-yl]-L-seryl-3-[3-α-D-mannopyranosy l-1-methyl-2-(methylimino)imidazolidin-4-yl]-D-seryl-L-seryl]bis-methiodide
    • Cyclo[glycyl-β-methylphenylalanyl-O-(methyl)tyrosyl-3-(1,3-dimethyl-2-(methylimino)imidazolidin-4-yl)seryl-3-[3-hexopyranosyl-1-methyl-2-(me thylimino)imidazolidin-4-yl]serylseryl]bis-methiodide
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-[1-benzyl-2-imino-3-α-D-mannopyranosyl-imidazolidin-4-yl]-D-seryl-L-seryl]
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1 -benzyl-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-[1-(4-tert-butylbenzyl)-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl]
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[2 -[1-(4-tert-butylbenzyl)-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-[2-imino-3-α-D-mannopyranosyl-1-(2-naphthylmethyl)-imidazolidin-4-yl]-D-seryl-L-seryl]
    • Cyclo[glycyl--methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3- hexopyranosyl-2-imino-1-(2-naphthylmethyl)-imidazolidin-4-yl]serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-[1,3-dibenzyl- 2-(benzylimino)imidazolidin-4-yl]-L-seryl-3- [1-benzyl-2-(benzylimino)-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[1,3-dibenzyl-2-(benzylimino)imidazo lidin-4-yl]seryl-3- [1-benzyl-2-(benzylimino)-3-hexopyranosylimidazolidin-4-yl]serylseryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(1-benzyl-2-imino-3-α-D-mannopyranosyl-imidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl- L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(1-benzyl-3-hexopyranosyl-2-iminoimidazolidin-4-yl)alanylserylglycyl-β-methylphenylalanyl-O-[4-O- [4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-[1,3-dimethyl- 2-(methylimino)imidazolidin-4-yl]-L-seryl-3- [3-α-D-mannopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]-D-seryl-L-seryl]bis-methiodide
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[1,3-dimethyl-2-(methylimino)imidazo lidin-4-yl]seryl-3-[3-hexopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]serylseryl]bis-methiodide
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazol idin-4-yl)-L-seryl-3-[1-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl]
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1 -(3,7-dimethylocta-2,6-dien-1-yl)-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-[1-heptyl-2-imino-3-α-D-mannopyranosyl-imidazolidin-4-yl]-D-seryl-L-seryl]
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1 -heptyl-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-[1-hexyl-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl]
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[ 3-hexopyranosyl-1-hexyl-2-iminoimidazolidin-4-yl]serylseryl]
    • Cyclo[3-[2-[2-(α-D-glucopyranosyloxy)phenyl-1,3-benzoxazol-5-yl]-D-alanyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(1-benzyl-2-imino-3-α-D-man nopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl];
    • Cyclo [3-[2-[2-(hexopyranosyloxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(1-benzyl-3-hexopyranosyl-2-iminoimidazoli din-4-yl)serylserylglycyl-β-methyl-phenylalanyl];
    • Cyclo[glycyl-(S)-D-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-d ecanoylimino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-decanoylimino-3-hexopyran osylimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(3-α -D-mannopyranosyl-2-(3-methyl-butyrylimino)-imidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-(3-methyl -butyrylimino)-imidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-( 2-ethyl-butyrylimino)-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-(2-ethyl-butyrylimino)-3- hexopyranosylimidazolidin-4-yl)serylseryl];
    • Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-man nopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazo lidin-4-yl)serylseryl];
    • N-[(Phenylmethoxy)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • N-[(Phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Tri-N-[(phenylmethoxy)carbonyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-[2-(pyrimidin-2-ylimino)imidazolidin-4-yl ]-L-seryl-3-[3-α-D-mannopyranosyl-2-imino-1-(pyrimidin-2-yl)imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(pyrimidin-2-ylimino)imidazolidin-4-yl]seryl-3-[3-hexopyran osyl-2-imino-1-(pyrimidin-2-yl)imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-[2-(1,3-benzoxazol-2-ylimino)imidazolidin -4-yl]-L-seryl-3-[1-(1,3-benzoxazol-2-yl)-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(1,3-benzoxazol-2-ylimino)imidazolidin-4-yl]seryl-3-[1-(1,3 -benzoxaxol-2-yl)-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-[2-(1,3-benzothiazol-2-ylimino)imidazolid in-4-yl]-L-seryl-3-[1-(1,3-benzothiazol-2-yl-3-α-D-mannopyranosyl)-2-iminoimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(1,3-benzothiazol-2-ylimino)imidazolidin-4-yl]seryl-3-[1-(1 ,3-benzo-thiazol-2-yl)-2-imino-3-hexopyranosylimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[3-( 6-O-hexanoyl-α-D-mannopyranosyl)-2-iminoimidazolidin-4-yl]-Dseryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-hexanoylhexopyranosy l)-2-iminoimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(6-O-hexanoyl-4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L -seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(6-O-hexanoyl-4-O-hexopyranosylhexopyranosyl)-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranos yl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(6-O-hexanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl) -L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(6-O-hexanoylhexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyrano syl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(diphenylacetyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolid in-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(diphenylacetyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hex opyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[3-[ 6-O-(diphenylacetyl)-α-D-mannopyranosyl]-2-iminoimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-p1-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-[6-O-(diphenylacetyl)hex opyranosyl]-2-iminoimidazolidin-4-yl]-serylseryl];
    • Cyclo[glycyl-(S)-C-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-i mino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-O-(diphenylacetyl)-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)seryl-O-(diphenylacetyl)-seryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[6-O-(diphenylacetyl)-4-O-α-D-mannopyranosyl-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin -4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[6-O-(diphenylacetyl)-4-O-hexopyranosylhexopyranosyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[3-( 6-O-heptanoyl-α-D-mannopyranosyl)-2-iminoimidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-heptanoylhexopyranos yl)-2-iminoimidazolidin-4-yl]seryl-seryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(6-O-heptanoyl-4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)- L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(6-O-heptanoyl-4-O-hexopyranosylhexopyranosyl)-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyrano syl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(6-O-heptanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl )-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(6-O-heptanoylhexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-i mino-3-(6-O-(phenylacetyl)-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-(6-O-(phenylacetyl)hexopy ranosyl-2-iminoimidazolidin-4-yl-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-i mino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-O-(phenyacetyl)-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl-seryl-O-(phenylacetyl)seryl];
    • Cyclo[glycyl-(S)-C-methyl-L-phenylalanyl-O-[4-O-α-D-mannopyranosyl-6-O-(phenylacetyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4 -yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-(phenylacetyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4—O-[6-O-(phenylacetyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin -4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(phenylacetyl)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexo pyranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-i mino-3-[6-O-(2-propylpentanoyl)-α-D-mannopyranosyl]-imidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-propylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3 -(6-O-(2-propylpentanoyl)-hexopyranosyl)-2-iminoimidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin -4-yl)-D-seryl-O-(2-propylpentanoyl)-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)seryl-O-(2-propylpentanoyl)-seryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-α-D-mannopyranosyl-6-O-(2-propyl-pentanoyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazol idin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-(2-propylpentanoyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(2-propylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-propylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-i mino-3-(6-O-(3-cyclopentylpropanoyl)-α-D-mannopyranosyl)-imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-(3-cyclopentylpropan oyl)-hexopyranosyl)-2-iminoimidazolidin-4-yl]serylseryl];
    • Cycloglycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-im ino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-O-(3-cyclopentylpropanoyl)-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)seryl-O-(3-cyclopentylpropanoyl)seryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[6-O-(3-cyclopentylpropanoyl)-4-O-α-D-mannopyranosyl-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimid azolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[6-O-(3-cyclopentylpropanoyl)-4-O-hexopyranosyl-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(3-cyclopentylpropanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-cyclopentylpropanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-α-D-mannopyranosyl-6-O-[(phenylmethoxy)-carbonyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-[(phenylmethoxy)carbonyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-[(phenylmethoxy)carbonyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(phenylmethoxy)carbonyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-phenethylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolid in-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-phenethylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-methoxyphenethylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-methoxyphenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-benzylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin- 4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(2,3-O-benzylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2iminoimidazolidin-4 -yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(2,3-O-benzylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin- 4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-cyclohexyl-L-alanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)- L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyr anosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-O-[4-O-[2,3-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)- L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-[4-O-[2,3-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyr anosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-O-[4-O-[2,3:4,6-di-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin -4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-[4-O-[2,3:4,6-di-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-methylbutylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimid azolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methylbutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-hexylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4 -yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-hexylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopy ranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-octylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4 -yl)-L-seryl-3-(2-imino-3-α-D -mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-octylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopy ranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O [4-O-[4,6-O-(3,3-dimethylbutylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D -mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,3-dimethylbutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-methylpentylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl);
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-methylpentylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(cyclohexylmethylene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclohexylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[2-[1-[(phenylmethoxy)carbonyl]-piperidin-4-yl]ethylidene]-α-D-mannopyranosyl]-α-D-ma nnopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[2-[1-[(phenylmethoxy)carbonyl]piperidin-4-yl]ethylidene]hexopyranosyl]hexopyranosyl]tyrosyl -3-(2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-butoxy-4-oxobutylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-butoxy-4-oxobutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(cyclohex-3-en-1-ylmethylene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclohex-3-en-1-ylmethylene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-ethylbutylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-ethylbutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(cyclopentylmethylene)α-mannopyranosyl]α-mannopyranosyl]-tyrosyl-3-(2-iminoimidazolid in-4-yl)-seryl-3-(2-imino-3αDmannopyranosylimidazolidin-4-yl)-seryl-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclopentylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-bromophenethylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-bromophenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-methylphenethylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-methylphenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-chlorophenethylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-B-methylphenylalanyl-O-[4-O-[4,6-O-(4-chlorophenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-fluorophenethylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-fluorophenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-cyclohexylethylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-cyclohexylethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(5-methylhex-4-en-1-ylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(5-methylhex-4-en-1-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylpropylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-i mino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-phenylpropylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2,6-dimethylhept-5-en-1-ylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3 -(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2,6-dimethylhept-5-en-1-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3,7-dimethyloct-6-en-1-ylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3- (2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,7-dimethyloct-6-en-1-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(1-adamantylmethylene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(1-adamantylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2,3-O-[2-(1-adamantyl)ethylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-[2-(1-adamantyl)ethylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[2-(1-adamantyl)ethylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[2-(1-adamantyl)ethylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3α-methoxy-5β-cholan-24-ylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3 -(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methoxycholan-24-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-(4-phenylbenzylidene)-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-(4-phenylbenzylidene)-hexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-thienylmethylene)-α-D-mannopyranosyl]-α-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-s eryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-thienylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-thienylmethylene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimid azolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-thienylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-methylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-methylbenzylidene)hexopyranosyl]-hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-methylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-hydroxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-hydroxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-methoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-chlorobenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-chlorobenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-isopropylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-isopropylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-propylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-propylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-carboxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-carboxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-ethoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-ethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(1,3-benzodioxol-5-ylmethylene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-( 2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(1,3-benzodioxol-5-ylmethylene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(methylthio)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(methylthio)benzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-naphthylmethylene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-naphthylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(2-methylprop-1-en-1-yl)-benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-ty rosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(2-methylprop-1-en-1-yl)benzylidene]-hexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidaz olidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-tert-butylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-tert-butylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-propyloxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-propyloxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[(2,3-dihydro-1,4-benzodioxan-6-yl)-methylene]-α-D-mannopyranosyl]-α-D-mannopyranosyl ]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[(2,3-dihydro-1,4-benzodioxan-6-yl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-imino imidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3,5-dimethoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,5-dimethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2,3-O-(3,5-dimethoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3,5-dimethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-methyl-4-nitrobenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methyl-4-nitrobenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-ethoxy-4-methoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-( 2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-ethoxy-4-methoxybenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-methoxy-4-nitrobenzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2 -iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methoxy-4-nitrobenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-phenylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimi dazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-phenylbenzylidene)hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-[2-[(2,2-dimethylpropanoyl)imino)imidazol idin-4-yl]-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-[(2,2-dimethylpropanoyl)iminoimidazolidin-4-yl]seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(3-pyridyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(3-pyridyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(methylsulfonyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-( 2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(methylsulfonyl)benzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[(6-chloro-1,3-benzodioxol-5-yl)-methylene]-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D -tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[(6-chloro-1,3-benzodioxol-5-yl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimi dazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6—O— [(6-methoxy-2-naphthyl)-methylene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-m annopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[(6-methoxy-2-naphthyl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2,3-O-[(6-methoxy-2-naphthyl)-methylene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl- 3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-[(6-methoxy-2-naphthyl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[(1-acetylindol-3-yl)methylene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-( 2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[1-(acetylindol-3-yl)methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(3-thienyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(3-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(2-thienyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(2-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(3-thienyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(3-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2,3-O-[4-(3-thienyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-[4-(3-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-[(3-methylbut-2-en-1-yl)oxy]-benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]- D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-(-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-[(3-methylbut-2-en-1-yl)oxy]-benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoim idazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(carboxymethoxy)benzylidene -α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D- seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(carboxymethoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-ethoxy-4-nitrobenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-ethoxy-4-nitrobenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(methylthio)-3-nitrobenzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl -3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(methylthio)-3-nitrobenzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidi n-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-hydroxy-3-methoxy-5-nitro-benzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-t yrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-hydroxy-3-methoxy-4-nitro-benzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimida zolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3-phenoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-phenoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-phenoxybenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-phenoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-[(E)-2-phenylethenyl]benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosy l-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(2-phenylethenyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-benzoylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoim idazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-benzoylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(4-methylphenoxy)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3- (2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-methylphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(phenylmethoxy)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2 -iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(phenylmethoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(phenylmethoxy)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2 -iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(phenylmethoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(4-chlorophenyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-( 2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(4-chlorophenyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(4-chloropheny)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2 -iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-chlorophenyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(1,1,2,2-tetrafluoroethoxy)-benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D -tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(1,1,2,2-tetrafluoroethoxy)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimi dazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(4-methoxyphenoxy)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3 -(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(4-methoxyphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(4-tert-butylphenoxy)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosy l-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-tert-butylphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolid in-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-[(4-nitrophenyl)methoxy]benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyr osyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-[(4-nitrophenyl)methoxy]benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazo lidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[[4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl)-oxy]benzylidene]-α-D-mannopyranosyl]-α-D-ma nnopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]-benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-( -2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-[3-(trifluoromethyl)phenoxy]-benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]- D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-[3-(trifluoromethyl)phenoxy]-benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoim idazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[[3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy]benzylidene]-α-D-mannopyran osyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(21iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-1-methylphenylalanyl-O-[4-O-[4,6-O-[[3-(3,7,1 1-trimethyldodeca-2,6,10-trien-1-yl)oxy]benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosy l-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(4-iodobenzoyl)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2 -iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-iodobenzoyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[4-(3,4,5-triiodobenzoyl)benz-ylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyro syl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(3,4,5-triiodobenzoyl)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazol idin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3,3-diphenylprop-2-enylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2 -iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,3-diphenylprop-2-enylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(prop-2-enylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(prop-2-enylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[4,6-O-[(6-methoxy-2-naphthyl)methylene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[ (6-methoxy-2-naphthyl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[4,6-O-[4-(phenylmethoxy)-benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[ 4-(phenylmethoxy)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-D-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[4,6-O-[3-(4-methoxy-phenoxy)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[ 3-(4-methoxyphenoxy)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[glycyl-(S)-4-chloro-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(cyclohexylmethylene)-α-mannopyranosyl]α-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3α-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclohexylmethylene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-4-chloro-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-methylpentylidene)-α-mannopyranosyl]α-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3α-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-methylpentylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-4-chloro-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-benzylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimid azolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-benzylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-3-iodo-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)hexopyranosyl]-3-iodotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[3-(4-methylphenoxy)benzylidene]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3- (2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(4-methylphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-cyclohexyl-L-alanyl-O-[4-O-[4,6-O-(3-phenylpropylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-y l)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-[4-O-[4,6-O-(3-phenylpropylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-O-[4-O-(4,6-O-benzylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl -3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2 -iminoimidazolidin-4-yl)-seryl-serylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-O-[4-O-[4,6-O-phenethylidene-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-se ryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-[4-O-[4,6-O-phenethylidene-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranos yl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[(3S)-3-cyclohexyl-L-2-aminobutanoyl-O-[4-O-[4,6-O-benzylidene-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin -4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexyl-2-aminobutanoyl-O-[4-O-[4,6-O-benzylidenehexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[glycyl-(S)-4-chloro-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-cyclopentylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclopentylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-cyclohexylidene-4-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazoli din-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclohexylidene-4-O-hexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(3S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-methylcyclohexylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-methylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2,2-dimethylcyclohexylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2,2-dimethylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2,6-dimethylcyclohexylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2,6-dimethylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(3,3,5,5-tetramethylcyclohexylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosy l-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,3,5,5-tetramethylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolid in-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-tert-butylcyclohexylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-tert-butylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-cyclododecylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclododecylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-cyclotridecylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclotridecylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(2,3-O-cyclotridecylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-cyclotridecylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(bicylo-[3.2.1]oct-2-ylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(bicylo-[3.2.1]oct-2-ylidene)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-bicyclo[3.3.1]non-9-ylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-bicyclo[3.3.1]non-9-ylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(4,6-O-tricyclo[5.2.1.0(2,6)]decan-2-ylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyros yl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-tricyclo[5.2.1.0(2,6)]decan-2-ylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)-α-D-mannopyranosyl]-α-D-mannopy ranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-o-methylphenylalanyl-O-[4-O-[4,6-O-(1,7,7-trimethylbicyclo[2.2. 1 ]hept-2-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl ];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]-α-D-mannopyranosyl]-α-D-mannopy ranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoi midazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(4-fluoro-α-methylbenzylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2 -iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-fluoro-α-methylbenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(tetrahydrothiopyran-4-ylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-( 2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(tetrahydrothiopyran-4-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-3-O-(3-methyl-butanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D- tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-3-O-(3-methyl-butanoyl)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimi dazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-( 2-adamantylidene)hexopyranosyl]-hexopyranosyl]tyrosyl];
    • Cyclo[glycyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)- L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyr anosyl-2-iminoimidazolidin-4-yl]-serylseryl];
    • Cyclo[(3S)-3-cyclohexyl-L-2-aminobutanoyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexyl-2-aminobutanoyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-3-[cis-4-[[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]oxy]cyclohexyl]-D-alanyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-3-[4-[[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[3-cyclohexyl-L-alanyl-3-[trans-4-[[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]oxy]cyclohexyl]-D-alanyl-3-(2- iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-3-[4-[[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(1-butyl-2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(1 -butyl-3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-[2-imino-3-α-D-mannopyranosyl-1-(3-methylbut-2-en-1-yl)imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3 -hexopyranosyl-2-imino-1-(3-methylbut-2-en-1-yl)imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-[2-imino-3-α-D-mannopyranosyl-1-[4-(trifluoromethyl)benzyl]imidazolidin-4-yl]-D-seryl-L-seryl]
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3 -hexopyranosyl-2-imino-1-[4-(trifluoromethyl)benzyl]imidazolidin-4-yl]serylseryl]
    • Di-N-(2-(1,3-benzoxazolyl))-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl ]-D-tyrosyl-3-[2-iminoimidazolidin-4-yl]-L-seryl-3-[2-imino-3-α-D-mannopyranosylimidazolidin-4-yl]-D-seryl-L-seryl]
    • Di-N-(2-(1,3-benzoxazolyl))-cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[2-imino imidazolidin-4-yl]seryl-3-[3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]
    • Di-N-(2-pyrimidinyl)-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl—O— [4-O-[4,6-O-(2-adamantylidene)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-[2-iminoimidazolidin-4-yl]-L-seryl-3-[2-imino-3-α-D-manno pyranosyl-imidazolidin-4-yl]-D-seryl-L-seryl]
    • Di-N-(2-pyrimidinyl)-cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[2-iminoimidazo lidin-4-yl]seryl-3-[3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(2,3-O-isopropylidene-4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin -4-yl)-L-seryl-3-[2-imino-3-(2,3-O-isopropylidene-α-D-mannopyranosyl)imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(2,3-O-isopropylidene-4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[2-imin o-(2,3-O-isopropylidene-hexopyranosyl)imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3-isopropylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3 -(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-imino-3-(2,3-O-isopropylidene-α-D-mannopyranosyl)imidazolidin-4-y]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3-isopropylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-[2-imino-3-(2,3-O-isopropylidenehexopyranosyl)imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3:4,6-di-O-iso-propylidene-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D -tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-imino-3-(2,3-O-isopropylidene-α-D-mannopyranosyl)imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3:4,6-di-O-isopropylidene-hexopyranosyl)hexopyranosyltyrosyl-3-(2-iminoimid azolidin-4-yl)seryl-3-[2-imino-(2,3-O-isopropylidenehexopyranosyl)imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[3-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-p-methylphenylalanyl-O-[4-O-[2-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-[4-(phenylmethoxy)benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-[4-(phenylmethoxy)benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2-O-[4-(phenylmethoxy)benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[3-O-[4-(phenylmethoxy)benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(4-methoxybenzyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazoli din-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-methoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(4-ethoxybenzyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolid in-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-ethoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hex opyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(4-methylbenzyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyrano sylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-methylbenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hex opyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(4-propoxybenzyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazoli din-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-propoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(4-phenoxybenzyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazoli din-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-phenoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(3-fluoro-4-methoxybenzyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-fluoro-4-methoxybenzyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(3-ethoxy-4-methoxybenzyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-ethoxy-4-methoxybenzyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-[4-methoxy-3-(phenylmethoxy)-benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl- 3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4-methoxy-3-(phenylmethoxy)benzyl]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-[4-methoxy-3-(phenylmethoxy)-benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl- 3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4-methoxy-3-(phenylmethoxy)benzyl]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-[(4-methoxy-1-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-[(4-methoxy-1-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2-O-[(4-methoxy-1-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(3,3-diphenylprop-2-en-1-yl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O[4-O-[6-O-(3,3-diphenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-(3,3-diphenylprop-2-en-1-yl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imi noimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(3,3-diphenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-[(2E)-3-phenylprop-2-en-1-yl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-phenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-[3-[4-(dimethylamino)phenyl](2E)-prop-2-en-1-yl]-α-D-mannopyranosyl]-α-D-mannopyranosyl ]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[3-[4-(dimethylamino)phenyl]prop-2-en-1-yl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimida zolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-[3-[4-(dimethylamino)phenyl](2E)-prop-2-en-1-yl]-α-D-mannopyranosyl]-α-D-mannopyranosyl ]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[3-[4-(dimethylamino)phenyl]prop-2-en-1-yl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimida zolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-(2-thienylmethyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazoli din-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-thienylmethyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[6-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[4-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[3-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[3-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[2-O-[(6-methoxy-2-naphthyl)methyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[2-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[6-O-[4-(phenylmethoxy)-benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-O-methyl-L-phenylal anyl-O-[4-O-[4-O-[4-(phenylmethoxy)-benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[3-O-[4-(phenylmethoxy)-benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[3-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[2-O-[4-(phenylmethoxy)-benzyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[2-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2,3:4,6-diisopropylidene-α-D-mannopyranosyl)-2-im inoimidazolidin-4-yl-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2,3:4,6-diisopropylidenehexopyranosyl)-2-iminoimidazolidin-4-y lserylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[3-(2,3::4,6-di-O-isopropylidene-α-D-mannopyranosy l)-2-iminoimidazolidin-4-yl]-D-seryl-O-(tert-butyldimethylsilyl)-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(2,3:4,6-di-O-isopropylidenehexopyranosyl)-2-iminoimidazolid in-4-yl]seryl-O-(tert-butyldimethylsilyl)seryl];
    • Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[3-(2,3:4,6-di-O-i sopropylidene-α-D-mannopyranosyl)-2-iminoimidazolidin-4-yl]-D-seryl-O-(tert-butyldimethylsilyl)-L-seryl];
    • Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(2,3:4,6-di-O-isopropylidene hexopyranosyl)-2-iminoimidazolidin-4-yl]seryl-O-(tert-butyldimethylsilyl)seryl];
    • Tetra-N-[(phenylmethoxy)carbonyl)-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazol idin-4-yl)-D-seryl-O-(tert-butyldimethylsilyl)-L-seryl];
    • Tetra-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyltyrosyt-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)ser yl-O-(tert-butyldimethylsilyl)seryl];
    • α-O-[(Pentylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • α-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • β-O-[(Pentylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • β-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • γ-O-[(Pentylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • γ-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • α-O-[(Butylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • α-O-[(Butylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • β-O-[(Butylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • β-O-[(Butylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • α-O-[(Heptylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • α-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl]-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • β-O-[(Heptylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • β-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • γ-O-[(Heptylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • γ-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • α-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimid azolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • α-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • β-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimid azolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • β-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • γ-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimid azolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • γ-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • α-O-[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosy l-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • α-O-[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • β-O-[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosy l-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • β-O-[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • α-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • α-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • β-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoi midazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • β-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • α-O-[(Benzylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • α-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • β-O-[(Benzylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • β-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • γ-O-[(Benzylamino)carbonyl]-cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimida zolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • γ-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-4-fluoro-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-ser yl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-fluoro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-4-fluoro-β-methyl-L-phenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-fluoro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-imino-imidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-4-fluoro-β-methyl-L-phenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-fluoro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-4-chloro-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-ser yl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-4-chloro-β-methyl-L-phenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-4-chloro-β-methyl-L-phenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-cyclohexyl-L-alanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-ma nnopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl];
    • Cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl]
    • Cyclo[glycyl-(S)-3-fluoro-β-methyl-L-phenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-3-fluoro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-3-fluoro-β-methyl-L-phenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)-β-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-3-fluoro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-3-fluoro-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-ser yl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-3-fluoro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[(3R)-3-(2-thienyl)-L-2-aminobutanoyl-O-[4-O-[2-O-(3-methylbutanoyl)α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[3-(2-thienyl)-2-aminobutanoyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[(3R)-3-(2-thienyl)-L-2-aminobutanoyl-O-[4-O-[3-O-(3-methylbutanoyl)α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[3-(2-thienyl)-2-aminobutanoyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]
    • Cyclo[(3R)-3-(2-thienyl)-L-2-aminobutanoyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2 -imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[3-(2-thienyl)-2-aminobutanoyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoim idazolidin-4-yl)serylserylglycyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-fluoro-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-ser yl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-fluoro-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-fluoro-O-[4-O-[2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-fluoro-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-fluoro-O-[4-O-[3-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-fluoro-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-amino-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-sery l-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-amino-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-i minoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-amino-O-[4-O-[2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-amino-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-3-amino-O-[4-O-[3-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-3-amino-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylglycyl-O-[4-O-[2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L- seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-phenylglycyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-2-chloro-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-ser yl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo [glycyl-2-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-imino imidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-2-chloro-β-methyl-L-phenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-2-chloro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-2-chloro-β-methyl-L-phenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imin oimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-2-chloro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[2-O-(4-methylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-(4-methylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-acetyl-3-O-(4-methylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-acetyl-3-O-(4-methylpentanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl]-O-[4-O-[4-O-(4-methylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidaz olidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(4-methylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[3-O-(3-methylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylpentanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3- hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-acetyl-3-O-(3-methylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-i minoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-acetyl-3-O-(3-methylpentanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-(3-methylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(3-methylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]; Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(2-O-butanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl) -L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2-O-butanoyl-hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(3-O-butanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl) -L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(3-O-butanoyl-hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(2-O-hexanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl) -L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2-O-hexanoyl-hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(3-O-hexanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl) -L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalany]-O-[4-O-(3-O-hexanoyl-hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(2-O-heptanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl )-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2-O-heptanoyl-hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyra nosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-(3-O-heptanoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl )-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl]; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(3-O-heptanoyl-hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyra nosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-O-methyl-L-phenylalanyl-O-[4-O-[6-O-acetyl-3-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-acetyl-3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]; Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-acetyl-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L -seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl]
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-acetyl-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[6-O-acetyl-2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-im inoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-acetyl-2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[2-O-(3-methylbutanoyl)α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[2-O-(3- methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl);
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-O-[4-O-[3-O-(3-methylbutanoyl)α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[3-O-(3- methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)- D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-hexopyranosyltyrosyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[4-O-[(2E)-2-methylbut-2-enoyl]-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-imino imidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(2-methylbut-2-enoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-imino-imidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-13-methyl-L-phenylalanyl-O-[4-O-[4-O-(2-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(2-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[4-O-[3-O-(4-methylpentanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazo lidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-(4-methylpentanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3- hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl ];
    • Cyclo[glycylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-ma nnopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylseryl]; Cyclo[glycyl-L-phenylalanyl-O-(4-O-[6-O-(2-methylpropanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L -seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-[4-O-[6-O-(2-methylpropanoyl)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyra nosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-O-(4-O-[3-O-(2-methylpropanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L -seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-[4-O-[3-O-(2-methylpropanoyl)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyra nosyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-O-(4-O-[6-O-(3-methylbutanoyl)-α-D-mannopyranosyl])-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L -seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-[4-O-[6-O-(3-methylbutanoyl)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-serylglycyl-(S)-β-methyl-L-phenylala nyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyran osylhexopyranosyl)tyrosyl];
    • Cyclo[3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-man nopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl];
    • Cyclo[3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-imi noimidazolidin-4-yl)seryl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-L-phenylalanyl-O-(4-O-α -D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycylphenylalanyl-O-(4-O-hexopyranosylhexo pyranosyl)tyrosyl]
    • Cyclo[glycyl-L-phenylalanyl-O-(4-O-[2-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L- seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-O-(4-O-[3-O-(3-methylbutanoyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L- seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-2-amino-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-sery l-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-2-amino-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-i minoimidazolidin-4-yl)serylseryl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-[α-D-mannopyranosyl]-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranos ylimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-hexopyranosyltyrosyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)sery lseryl];
    • Cyclo[3-cyclohexyl-L-alanyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-seryl-L-seryl glycyl];
    • Cyclo[3-cyclohexylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)-L-alanyl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D-alanyl-L-serylglycyl-(S)-β-methyl-L-phenylal anyl-D-tyrosyl];
    • Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyltyrosyl];
    • Cyclo[(3S)-3-cyclohexyl-L-2-aminobutanoyl-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-imino-3-α-D-mannopyranosylimidazolidin-4-yl)-D -seryl-L-serylglycyl];
    • Cyclo[3-cyclohexyl-2-aminobutanoyl-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl];
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(2,3-O-isopropylidene-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-[2-imi no-3-(2,3-O-isopropylidene-α-D-mannopyranosyl)imidazolidin-4-yl]-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(2,3-O-isopropylidene-hexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[2-imino-(2,3-O-isopropy lidene-hexopyranosyl)imidazolidin-4-yl]serylseryl];
    • Cyclo[glycyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-iminoimidazoli din-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl]
    • Cyclo[glycyl-(S)-β-methyl-L-phenylalanyl-O-(4-O-α-D-mannopyranosyl-α-D-mannopyranosyl)-D-tyrosyl-3-(2-iminoimidazolidin-4-yl)-L-seryl-3-(2-i minoimidazolidin-4-yl)-D-seryl-L-seryl];
    • Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)se rylseryl].

An aspect of the invention is a process for producing a compound of the formula: embedded image
wherein:

    • R1 is selected from: embedded image
    • R1a is H;
    • R2 is a moiety embedded image
    • R2a is selected from embedded image
    • R2b is H;
    • R2c is H;
    • R3 and R4 are independently H or OH;
    • R5 is H or embedded image
    • R6a, R6b, R6c, R6d, or R6e are H;
    • R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are independently
    • H, or —C(O)—Y-Z;
    • Y is a single bond;
    • Z is straight or branched chain alkyl(C1-C20) or straight or branched chain alkenyl(C2-C20);
    • which process comprises:
    • cultivating a glycopeptide antibiotic producing strain of Streptomyces hygroscopicus selected from the group LL4600, LL4614, LL4666, LL4690, LL4728, LL4741, LL4742, LL4744, LL4773, LL4779, LL4783, LL4902, BD2, BD20 and BD70 or a mutant thereof under aerobic conditions, in a suitable culture medium until a recoverable amount of said antibiotic is formed in said medium and recovering said antibiotic therefrom. Preferred aspects of the process include:
    • a.) R7, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H; and
    • Z is straight or branched chain alkyl(C1-C9) or straight or branched chain alkenyl(C2-C10);
    • b.) R7, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H;
    • Z is straight or branched chain alkyl(C1-C9) or straight or branched chain alkenyl(C2-C10);
    • R3 and R4 are H;
    • c.) R7, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H;
    • Z is straight or branched chain alkyl(C1-C9) or straight or branched chain alkenyl(C2-C10); and
    • R3 and R4 are OH; and
    • d.) the glycopeptide antibiotic produced has the structure selected from the group embedded image embedded image

Another aspect of the invention is the preparation by fermentation means in a liquid media using modified strains of Streptomyces hygroscopicus selected from the group LL4600, LL4614, LL4666, LL4690, LL4728, LL4741, LL4742, LL4744, LL4773, LL4779, LL4783, LL4902, BD2, BD20 and BD70 or mutants thereof glycopeptide antibiotics of the formula embedded image
wherein:

    • R1 is selected from: embedded image
    • R1a is H or halogen;
    • R2 is a moiety embedded image
    • R2a is selected from embedded image
    • R2b is H, F, or NH2;
    • R2c is H;
    • R3 and R4 are independently H or OH;
    • R5 is H or embedded image
    • R6a, R6b, R6c, R6d, or R6e are H;
    • R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are independently H, or —C(O)—Y—Z;
    • Y is a single bond;
    • Z is straight or branched chain alkyl(C1-C20) or straight or branched chain alkenyl(C2-C20);
    • by the addition of substrates of the formulae:
    • straight or branched chain alkyl(C1-C20)CO2H, straight or branched chain alkenyl(C2-C20)CO2H, embedded image
      and detecting and/or recovering the antibiotic. In an additional aspect of the process multiple substrates may optionally be added. For example, straight or branched chain alkyl(C1-C20)CO2H and embedded image
      may optionally be added.

Preferred aspects of the process include:

    • a.) R7, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H; and
    • Z is straight or branched chain alkyl(C1-C9) or straight or branched chain alkenyl(C2-C10);
    • b.) R7, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H;
    • Z is straight or branched chain alkyl(C1-C9) or straight or branched chain alkenyl(C2-C10); and
    • R3 and R4 are H; or
    • c.) R7, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H;
    • Z is straight or branched chain alkyl(C1-C9) or straight or branched chain alkenyl(C2-C10); and
    • R3 and R4 are OH.

A further aspect of the invention is the preparation by fermentation means in a liquid media using modified strains of Streptomyces hygroscopicus selected from the group LL4600, LL4614, LL4666, LL4690, LL4728, LL4741, LL4742, LL4744, LL4773, LL4779, LL4783, LL4902, BD2, BD20 and BD70 or mutants thereof glycopeptide antibiotics of the formula embedded image
wherein:

    • R1 is selected from: embedded image
    • R1a is H or halogen;
    • R2 is a moiety embedded image
    • R2a is selected from embedded image
    • R2b is H, F, or NH2;
    • R2c is H;
    • R3 and R4 are independently H or OH;
    • R5 is H or embedded image
    • R6a, R6b, R6c, R6d, or R6e are H;
    • R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are independently H, or —C(O)—Y-Z;
    • Y is a single bond;
    • Z is straight or branched chain alkyl(C1-C20) or straight or branched chain alkenyl(C2-C20);
    • by the addition of suitable substrates of the formulae:
    • straight or branched chain alkyl(C1-C20)CO2H, straight or branched chain alkenyl(C2-C20)CO2H, embedded image
      and detecting and/or recovering the antibiotic.

It is understood herein that when a compound of the invention contains asymmetric carbons, that they encompass all possible regioisomers, stereoisomers and mixtures thereof. In particular, the definitions encompass any optical isomers and diastereomers, as well as the racemic and resolved, enantiomerically pure R and S stereoisomers, as well as other mixtures of the R and S stereoisomers and pharmaceutically acceptable salts thereof. Optical isomers may be obtained in pure form by standard separation techniques.

Glycopeptide compounds of the formula according to the invention may contain mobile hydrogen atoms and consequently be present in different tautomeric forms. One skilled in the art will recognize that said tautomers often exist in equilibrium with each other. As these tautomers interconvert under physiological conditions, they provide the same useful antibacterial effects. The present invention includes mixtures of such tautomers as well as the individual tautomers of compounds of the invention. Compounds of Formula I where R5, R6a, R6b, R6c, R6d, or R6e are not H may for regioisomeric products which are represented by the formulae: embedded image embedded image embedded image

In the same regard, any substituents R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29 of the compounds of the invention above and below, may be represented by their alternative tautomeric forms, where appropriate, as is known to those skilled in the art.

For the compounds of the invention defined above and referred to herein, unless otherwise noted, the following terms are defined:

Halogen, as used herein means fluoro, chloro, bromo and/or iodo.

Alkyl as used herein means a branched or straight chain radical having from 1 to 20 (preferably 1 to 6) carbon atoms optionally substituted with one or more groups selected from halogen, cyano, nitro, hydroxy, sulfhydryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, thioalkylo thioaryl, acyl, aroyl, acyloxy, acylamino, carboxy, carboxyalkyl, carboxyaryl, carboxamido, carboxamidoalkyl, carboxamidodialkyl, alkylsulfonamido, arylsulfonamido, aryl, and heteroaryl. Exemplary alkyl groups include but are not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl and hexyl, also optionally substituted, as well as perfluoroalkyl.

Alkenyl as used herein means a branched or straight chain radical having from 2 to 20 (preferably 2 to 6) carbon atoms optionally substituted with one or more groups selected from halogen, cyano, nitro, hydroxy, sulfhydryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, thioalkyl, thioaryl, acyl, aroyl, acyloxy, acylamino, carboxy, carboxyalkyl, carboxyaryl, carboxamido, carboxamidoalkyl, carboxamidodialkyl, alkylsulfonamido, arylsulfonamido, aryl, and heteroaryl, with the chain containing at least one carbon-carbon double bond. Alkenyl, may be used synonymously with the term olefin and includes alkylidenes. Exemplary alkenyl groups include but are not limited to ethylene, propylene and isobutylene.

Alkynyl as used herein means a branched or straight chain radical having from 2 to 20 (preferably 3 to 10) carbon atoms optionally substituted with one or more groups selected from halogen, cyano, nitro, hydroxy, sulfhydryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, thioalkyl, thioaryl, acyl, aroyl, acyloxy, acylamino, carboxy, carboxyalkyl, carboxyaryl, carboxamido, carboxamidoalkyl, carboxamidodialkyl, alkylsulfonamido, arylsulfonamido, aryl, and heteroaryl. The chain contains at least one carbon-carbon triple bond.

Cycloalkyl as used herein means a saturated monocyclic or polycyclic fused, bridged, or spirocyclic ring system having from 3 to 20 carbon atoms. Exemplary cycloalkyl rings include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, [2.2.1]-bicycloheptanyl, [2.2.2]-bicyclooctanyl, adamantyl, [3.3.1]-bicyclononanyl, spiro-[4.4]-nonanyl, spiro-[4.5]-decanyl, spiro-[5.5]-undecanyl, and the like.

Aryl as used herein means a homocyclic or polycyclic aromatic radical, fused or catenated, having 6 to 20 carbon atoms independently substituted with one to three substituents selected from the group of alkyl, halogen, cyano, nitro, hydroxy, sulfhydryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, thioalkyl, thioaryl, acyl, aroyl, acyloxy, acylamino, carboxy, carboxyalkyl, carboxyaryl, carboxamido, carboxamidoalkyl, carboxamidodialkyl, alkylsulfonamido, arylsulfonamido, aryl, or heteroaryl. Examples include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, and anthracenyl, optionally substituted with one to three substituents.

Alkoxy as used herein means an alkyl-O— group in which the alkyl group is as previously described. Exemplary alkoxy groups include but are not limited to methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, and t-butoxy.

Aryloxy as used herein means an aryl-O— group in which the aryl group is as previously described.

Thioalkyl as used herein means an alkyl-S— group in which the alkyl group is as previously described.

Thioaryl as used herein means an aryl-S— group in which the aryl group is as previously described.

Acyl as used herein means an alkyl-C(O)— group in which the alkyl group is as previously described.

Aroyl as used herein refers to an aryl-C(O)— group in which the aryl group is as previously defined. Examples include but are not limited to benzoyl and naphthoyl.

Acyloxy as used herein means an alkyl-C(O)O— group or an aryl-C(O)O— group in which the alkyl or aryl group is as previously described.

Acylamino as used herein means an alkyl-C(O)N═ group or an aryl-C(O)N═ group in which the alkyl or aryl group is as previously described.

Carboxyalkyl as used herein means an alkyl-OC(O)— group in which the alkyl group is as previously defined.

Carboxyaryl as used herein means an aryl-OC(O)— group in which the aryl group is as previously defined.

Carboxyamido as used herein means a NH2C(O)— group.

Carboxyamidoalkyl as used herein means an alkyl-NHC(O)— group in which the alkyl group is as previously defined.

Carboxyamidodialkyl as used herein means a dialkyl-NC(O)— group in which the alkyl groups are as previously defined.

Alkylsulfondamido as used herein means an alkyl-S(O)2—N═ group in which the alkyl group is as previously defined.

Arylsulfonamido as used herein means an aryl-S(O)2—N═ group in which the aryl group is as previously defined.

Heteroaryl denotes a 5- or 6-membered heterocyclic ring, which may be fused to another 5- or 6-membered heterocyclic ring or non-heterocyclic ring, especially heteroaromatic rings which contain 1 to 3 heteroatoms which may be the same or different. Nitrogen, oxygen and sulfur are the preferred heteroatoms provided that the heterocyclic ring does not contain —O—O—, —S—S— and —S—O— bonds. A heteroaryl group may be optionally substituted with 1 to 3 substituents selected from the group halogen, cyano, nitro, hydroxy, sulfhydryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, thioalkyl, thioaryl, acyl, aroyl, acyloxy, acylamino, carboxy, carboxyalkyl, carboxyaryl, carboxamido, carboxamidoalkyl, carboxamidodialkyl, alkylsulfonamido, arylsulfonamido, aryl, and heteroaryl. Exemplary heteroaryl groups include but are not limited to furan, thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyridine, pyrimidine, pyrazine, pyridazine, indole, quinoline, isoquinoline, benzimidazole, quinazoline, and the like.

Where terms are used in combination, the definition for each individual part of the combination applies unless defined otherwise. For instance, aralkyl refers to an aryl group, and alkyl refers to the alkyl group as defined above.

The compounds of the invention may be obtained as inorganic or organic salts using methods known to those skilled in the art (Richard C. Larock, Comprehensive Organic Transformations, VCH publishers, 411-415, 1989). It is well known to one skilled in the art that an appropriate salt form is chosen based on physical and chemical stability, flowability, hydroscopicity and solubility.

Pharmaceutically acceptable salts of the compounds of the invention include basic salts of inorganic and organic acids, including but not limited to hydrochloric acid, hydrobromic acid, sulphuric acid, phosphoric acid, nitric acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, napthalenesulfonic acid, camphorsulfonic acid, malic acid, acetic acid, trifluroacetic acid, oxalic acid, malonic acid, tartaric acid, citric acid, lactic acid, fumaric acid, succinic acid, maleic acid, salycylic acid, benzoic acid, phenylacetic acid, mandelic acid and the like.

When compounds of the invention include an acidic function such as a carboxy group, then suitable pharmaceutically acceptable salts of the compounds of the invention with an acidic moiety can be formed from organic and inorganic bases. Such includes but is not limited to salts formed with alkali metals or alkaline earth metals such as sodium, potassium, lithium, calcium, or magnesium or organic bases such as triethylamine, N,N-diethylmethylamine, N,N-diethylethylenediamine, and N-tetraalkylammonium salts such as N-tetrabutylammonium salts. For additional examples of “pharmaceutically acceptable salts” see Berge et al, J. Pharm. Sci. 66, 1 (1977).

The compounds can also be used in the form of esters, carbonates, carbamates and other conventional prodrug forms, which when administered in such form, convert to the active moiety in vivo.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

This invention uses as starting materials for the preparation of certain compounds of the invention, a variety of glycopeptide antibiotics prepared by fermentation. In particular, using the fermentation conditions described in U.S. Pat. No. 3,495,004 a complex of antibiotics is isolated. Optionally, using hereindescribed fermentation conditions, with Streptomyces hygroscopicus strain LL4600, the complex may also be prepared. Further separation of the complex of antibiotics by HPLC into individual components AC-98-1, AC-98-2, AC-98-3, AC-98-4 and AC-98-5 and determination of the chemical structures by spectroscopy is described in copending provisional patent application Docket Number 33447, 60/286,249, filed Apr. 25, 2001. The structures of the individual components are shown below.

R1R2R3R4R5
AC- 98-1 embedded image embedded image OHOH embedded image
AC- 98-2 embedded image embedded image OHOH embedded image
AC- 98-3 embedded image embedded image OHOH embedded image
AC- 98-4 embedded image embedded image OHOH embedded image
AC- 98-5 embedded image embedded image OHOH embedded image

Certain compounds of the invention are prepared by fermentation means using modified strains of Streptomyces hygroscopicus selected from the group LL4600, LL4614, LL4666, LL4690, LL4728, LL4741, LL4742, LL4744, LL4773, LL4779, LL4783, LL4902, BD2, BD20 and BD70 and mutants thereof and include those of the formula embedded image
wherein:

    • R1 is selected from: embedded image
    • R1a is H or halogen;
    • R2 is a moiety embedded image
    • R2a is selected from embedded image
    • R2b is H, F or NH2;
    • R2C is H;
    • R3 and R4 are independently H or OH;
    • R5 is H or embedded image
    • R6a, R6b, R6c, R6d, or R6e are H;
    • R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are independently H, or —C(O)—Y-Z;
    • Y is a single bond;
    • Z is straight or branched chain alkyl(C1-C20) or straight or branched chain alkenyl(C2-C20);
    • by directed biosynthetic fermentations through the addition of substrates of the formulae:
    • straight or branched chain alkyl(C1-C20)CO2H, straight or branched chain alkenyl(C2-C20)CO2H, embedded image
      using controlled conditions in a suitable media, optionally containing mannose, under aerobic conditions and isolating the antibiotics which optionally may be further chemically modified. Multiple substrates may optionally be added.

For example cultivating streptomyces hygroscopicus LL4614 in the presence of p-chloro-DL-phenylalanine affords recoverable quantities of glycopeptide antibiotics cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] and cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl].

A further aspect of the invention is to recover glycopeptide antibiotics of the invention wherein R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H by hydrolysis of mixtures where R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H or esters (—C(O)—Y-Z) by adding base which includes sodium hydroxide and the like or (3-[cyclohexylamino]-1-propanesulfonic acid)to the medium at about O° to about 25° C., preferred is about O° to about 4° C. at a pH of about 8.0 to about 13.5, preferred about 11.5 to about 13.5 and recovering said antibiotic at a pH of about 1.8 to about 6.5 preferred is about 4.0 to about 6.0. The pH is adjusted from about 8.0 to about 13.5 to about 1.8 to about 6.5 with acids which include hydrochloric acid, acetic acid, propanoic acid and (3-[N-morpholino]propanesulfonic acid). Preferably the acid adjusted pH is about 4.0 to about 5.0. Optionally buffers may also be used to adjust pH. Optionally, mixtures where R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H or esters (—C(O)—Y-Z) may first be isolated from the medium and then hydrolyzed as described hereinabove.

Certain of the glycopeptide antibiotics of the invention are produced by fermentation of mutant derivative strains of Streptomyces hygroscopicus LL4600. These microorganisms listed in Table 1 are maintained in the culture collection of American Home Products, Wyeth-Ayerst Discovery, Pearl River, N.Y. as culture numbers LL4600, LL4614, LL4666, LL4690, LL4728, LL4741, LL4742, LL4744, LL4773, LL4779, LL4780, LL4783, LL4902, BD2, BD20 and BD70. A viable culture of these new microorganisms is deposited under the Budapest Treaty with the Patent Culture Collection Laboratory, Northern Regional Research Center, U.S. Department of Agriculture, Peoria, Ill. 61604, and added to its permanent collection.

TABLE 1
Wyeth-Ayerst cultureNRRL culture
collection #collection
LL4600NRRL 30439
LL4614NRRL 30440
LL4666NRRL 30441
LL4690NRRL 30442
LL4728NRRL 30443
LL4741NRRL 30444
LL4742NRRL 30445
LL4744NRRL 30446
LL4773NRRL 30447
LL4779NRRL 30448
LL4780NRRL 30449
LL4783NRRL 30450
LL4902NRRL 30451
BD2NRRL 30452
BD20NRRL 30453
BD70NRRL 30454

It is to be understood that the production of certain glycopeptide antibiotics of the invention by fermentation is not limited to the particular mutants defined above which are for illustrative purposes only. In fact, it is desired and intended to include the use of mutants as described herein and those produced by additional exposure of the above defined mutants to X-radiation, ultraviolet radiation, N′-methyl-N′-nitro-N-nitrosoguanidine, ethyl-methane sulfonate and the like. Strains presented are all derivatives of NRRL 3085. A culture stock designated LL4600 is derived from NRRL 3085 by colony purification and served as the starting point for the work described.

Mutants accumulating biosynthetic intermediates, shunt metabolites or compounds not detected in LL4600 are derived by NTG mutagenesis of LL4600 or various industrial derivatives of LL4600.

Mutagenesis

The described strains are obtained via N-methyl-N′-nitro-N-nitrosoguanidine (NTG) mutagenesis. Cells are grown in TSBG (Tryptic soy broth [Difco] supplemented with 20 g/L glucose) for 24-48 hours and then are sonicated for 5-40″ to disperse mycelial pellets to variably-sized mycelial fragments. The sonicated suspension is pelleted, resuspended in fresh TSBG containing 50-1000 μg/mL NTG and dosed for 10-260 min at 30° C. with shaking. The dosed cells are then pelleted, resuspended in fresh TSBG and grown overnight at 30° C. The overnight cells are then sonicated for 6-20″ to disrupt mycelial pellets. The mutagenized cells are stored as a 20% glycerol stock at −70° C.

Cultivation

Cultivation of mutant strains of Streptomyces hygroscopicus designated above may be carried out in a wide variety of liquid culture media. Media which are useful for the production of glycopeptide antibiotics include an assimilable source of carbon, such as dextrin, dextrose, sucrose, molasses, starch, glycerol, etc; an assimilable source of nitrogen such as protein, protein hydrolysate, polypeptides, amino acids, corn steep liquor, etc; and inorganic anions and cations, such as potassium, sodium, ammonium, calcium, sulfate, carbonate, phosphate, chloride, etc. Trace elements such as zinc, cobalt, iron, boron, molybdenum, copper, etc., are supplied as impurities of other constituents of the media. Aeration in tanks and bottles is supplied by forcing sterile air through or onto the surface of the fermenting medium. Aeration provides for aerobic fermentations. Further agitation in tanks is provided by a mechanical impeller. An antifoam agent such as polypropylene glycol may be added as needed.

Culture preservation

Strains are preserved as frozen whole cells (frozen vegetative mycelia, FVM) prepared from cells grown for 24-48 hours in TSBG (Tryptic soy broth [Difco] supplemented with 20 g/L glucose). Glycerol is added to 20% and the cells are frozen at −70° C.

Inoculum Development Fermentation In Suitable Culture Media and Conditions

Composition of suitable culture media used in the examples presented is as follows:

Composition of fermentation media
BPM17statBPM17statBPM27-
ComponentBPM17BPM17statgalmanBPM27man
Pharmamedia10 g/L20 g/L20 g/L20 g/L20 g/L20 g/L
(Traders)
Glucose40 g/L60 g/L60 g/L60 g/L60 g/L60 g/L
Galactose20 g/L
Mannose 2 g/L 2 g/L
CaCO3 5 g/L 5 g/L 5 g/L 5 g/L
(Mississippi
Lime)
CaCO315 g/L15 g/L
(Gamaco)

Fermentations are inoculated from cells grown in TSBG medium at 30° C. for 24-48hr with shaking on a gyrorotary shaker. Shake-flask fermentations are performed at 30° C. for 3-5 days on a gyro-rotary shaker operating at 250 rpm (2″ stroke). Ten-liter fermentations are performed at 30° C. for 3-5 days at 30° C, at 400-800 rpm with 1 vvm airflow. Fermentation at 300 liters is similarly performed with agitation at 170-200 rpm. Antifoam, such as Macol P2000 is added to fermentor medium at 0.2-2.0%. Three hundred-liter fermentations with medium BPM17statgal employ galactose at 8 g/L. The strains described may be fermented in any of the media listed above beyond the specific examples herein described.

Biotransformation Methods

Substrates are prepared as 5 mg/mL stock solutions in water and filter sterilized. The stock solution is added to BPM17statgal shake-flasks (each containing 25 mL of medium) to give a final concentration of 100 mg/L. Substrate compounds are added at the time of inoculation. Fermentations are conducted for 3 days.

Hydrolysis of Esters

Compounds of the invention, prepared by fermentation may be isolated as mixtures which include esters. Alternatively, and in particular, mixtures of esters wherein R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are independently H or —C(O)—Y-Z ; Y is a single bond; and Z is straight or branched chain alkyl(C1-C20) or straight or branched chain alkenyl(C2-C20) may optionally be hydrolyzed following fermentation and preferably before isolation of antibiotics by adding suitable bases to the broth which include: aqueous sodium hydroxide and (3-[cyclohexylamino]-1-propanesulfonic acid) CAPS and the like and adjusting the pH with hydrochloric acid, acetic acid or (3-[N-morpholino]propanesulfonic acid) MOPS and the like to afford products where R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21 and R22 are H followed by recovery of the antibiotics.

Analytical HPLC Analysis of Gycopeptide Antibiotics

Cells are removed for fermentation broth by centrifugation. The clarified supernatant is applied to a wetted BAKERBOND™ spe carboxylic acid extraction column (catalog # 7211-03). Columns are washed with 50% aqueous methanol and eluted with acetonitrile/water/trifluoroacetic acid (70/30/0.5). The solvent is evaporated, and the residue is reconstituted in 0.2-0.4 mL methanol/water (1/1). In some instances supernatants are analyzed directly. Samples are analyzed using a Hewlett Packard model 1090 liquid chromatograph with photodiode array detection. The compounds are resolved by reverse phase chromatography using a YMC ODS-A 4.6×150 mm HPLC column, with a mobile phase of 10% acetonitrile: 0.01% trifluoroacetic acid (solvent A) and 50% acetonitrile:0.01% trifluoroacetic acid (solvent B). A linear gradient from 0% B to 100% B in 22 min, with a flow rate of 1 mL/min, is used for elution. Novel metabolites are identified by the appearance of HPLC peaks which possess characteristic UV absorption spectra but displayed novel retention times. Relative retention times (RRT) are calculated by dividing the peak retention times of novel compounds of the invention by that of (Example 281a) Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl]. Subsequent LC/MS analysis is then performed on fermentation extracts to determine molecular weights.

LC/MS Analysis of Glycopeptide Antibiotics from Fermentations

The molecular weights of new glycopeptide antibiotics from fermentations are determined using a Hewlett-Packard API-electrospray LC/MS system with an HP 5989B Mass Spectrometer, HP 59987A API-Electrospray, HP 1090 series II HPLC and HP ChemStation data system with HP G1047A LC/MS software. Extracts are resolved by reverse phase HPLC as described above. UV detection is at 226 nm. The MS electrospray is performed in positive mode with a scan range of 400-1700 m/z.

General Procedure for the Isolation of Fermentation Products

Typical representative methods for the recovery and isolation of glycopeptide antibiotics of the invention from the fermentation broth include:

    • a) loading fermentation broth on polyacrylate resin, XAD-7, prewashed sequentially with methanol, acetone and water. Eluting the resin with 1:1 acetonitrile-water containing 0.1% trifluoroacetic acid, concentrating under reduced pressure to a small volume then extracting with 1:4 water-N,N-dimethylformamide and fractionating the residue of the evaporated extract by reverse phase HPLC on a C18 column by elution with a gradient of acetonitrile-water containing trifluoroacetic acid;
    • b) using method a) above and fractionating the residue by reverse phase HPLC on a C18 column by elution with a gradient of methanol-water containing trifluoroacetic acid;
    • c) loading fermentation broth on CG-61 resin, and eluting with 40%:60% acetonitrile-water containing 0.01% trifluoroacetic acid, concentrating product fractions under reduced pressure and adjusting the pH to 12.5 with sodium hydroxide for 45 min to 3 h or until esters are hydrolyzed. Adjusting the pH to 3.0 with hydrochloric acid and collecting the antibiotic from acetonitrile;
    • d) adding diatomaceous earth to the fermentation, filtering and adjusting the pH of the filtrate to pH 12.8 with sodium hydroxide and holding for up to 3 h, neutralizing with acetic acid and loading on SP207 resin. Washing the resin with water, methanol and eluting with 1:1 methanol-water-3% acetic acid and collecting product from concentrated fractions with isopropanol-acetonitrile.
    • e) adding an equal volume of 50 mM CAPS buffer (pH 13) to the fermentation broth until esters have been hydrolyzed, adding three volumes of 1M MOPS buffer (pH 7.0) to neutralized the mixture and loading on a CG-71C column, eluting with 1:1 acetonitrile-water-0.05% trifluoroacetic acid and purifying antibiotic product fractions by reverse phase HPLC on a C18 column using a gradient of methanol-water-0.05% trifluoroacetic acid; or
    • f) adding an equal volume of 50 mM CAPS buffer (pH 13) to the fermentation broth until esters are hydrolyzed, adding three volumes of 1M MOPS buffer (pH 7.0) to neutralized the mixture and separating antibiotic product by reverse phase HPLC on a C18 column by elution with 10%-90% acetonitrile-water containing 0.01% trifluoroacetic acid.

Further preparation of compounds of this invention is described below and is illustrated in the following Schemes.

Compounds of this invention may be prepared as shown in Scheme I by nitrations and halogenations of glycopeptide antibiotics 1 to give glycopeptide antibiotics 2 which may be further modified by herein described subsequent transformations. Halogenation of glycopeptide antibiotics 1 to afford glycopeptide antibiotics 2 may be achieved by methods known to those skilled in the art, including treatment with bromine, iodine, sodium hypochlorite, N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinimide, iodine monochloride, benzyltrimethylammonium dichloroiodate, and the like, in a solvent which include a concentrated mineral acid, such as aqueous hydrochloric acid, sulfuric acid, and the like, or a concentrated carboxylic acid such as acetic acid or trifluoroacetic acid, and the like, at temperatures about 0° to about 30° C. Nitration of glycopeptide antibiotics 1 to afford glycopeptide antibiotics 2 may be achieved by methods known to those skilled in the art, by treatment with nitrating reagents, which include metal nitrate salts including potassium nitrate in a solvent such as a concentrated mineral acid or a concentrated carboxylic acid such as acetic acid or trifluoroacetic acid, at temperatures about −20° C. to about 30° C. embedded image

As further shown in Scheme II, compounds in which R2b and/or R2c of glycopeptide antibiotics 2 are bromine or iodine serve as precursors to compounds of formula 3 wherein R2b and/or R2c are alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), aryl and heteroaryl, all of which may be prepared by transition metal mediated coupling reactions, which include the palladium(0) mediated couplings of aryl bromides or iodides with organostannanes which include (R2b)4Sn, (R2c)4Sn, R2bSn(butyl)3 or R2CSn(butyl)3, and the like (Stille couplings; as described in Farina, V. and Roth, G. P. Advances in Metal-Organic Chemistry 1996, 5, 1-53 and references therein), with organoboron compounds which include R2b-(9-borabicyclo[3.3.1]nonane) (R2b-9-BBN), R2c-(9-borabicyclo[3.3.1]nonane) (R2c-9-BBN), R2b—B(OH)2, R2c—B(OH)2, R2b—B(O-alkyl(C1-C20))2, R2c—B(O-alkyl(C1-C20))2, embedded image
(Suzuki couplings; as described in Miyaura, N. and Suzuki, A. Chem. Rev. 1995, 95, 2457-2483 and references therein), or with alkenes or terminal alkynes (Heck couplings; as described in de Meijere, A. and Meyer, F. E. Angew. Chem. Int. Ed. Eng. 1994, 33, 2379-2411 and references therein). In those instances wherein the transition metal mediated coupling reaction is a palladium(O) mediated coupling of a terminal alkyne with glycopeptide antibiotics 2, wherein R2a is H, the formation of products 3a containing a benzofuran moiety may also be produced. embedded image

Scheme III describes the synthesis of amine 4 in which R2b is —NH2 which maybe prepared from the corresponding glycopeptide antibiotic 2 in which R2b is —NO2, by reduction using standard methods known to those skilled in the art, including hydrogenation under an atmosphere of hydrogen at pressures from about 1 to about 250 psi, over a suitable catalyst such as palladium or platinum, and the like, either alone or adsorbed onto a suitable support such as carbon, alumina or diatomaceous earth, in solvents such as water, methanol, ethanol, and the like, alone or in combination, in the presence or absence of a mineral or carboxylic acid, such as hydrochloric acid, sulfuric acid, or acetic acid, at temperatures from about 25° C. to the reflux temperature of the solvent. Alternatively, amine 4 may also be prepared by the reduction of glycopeptide antibiotic 2 over metals such as iron or zinc in solvents such as water, methanol, ethanol, and the like, alone or in combination, in the presence of a mineral or carboxylic acid, such as hydrochloric acid, sulfuric acid, or acetic acid, at temperatures from ambient temperature to the reflux temperature of the solvent. embedded image

As further described in Scheme IV, amine 5 in which R2b is —NR2fR2g, wherein R2f is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20) and R2g is H, may be prepared from amine 4 in which R2b is —NH2, by methods known to those skilled in the art, such as by alkylation with an appropriate alkyl halide R2fX, where X is Cl, Br, I, —O-tosylate, —O-mesylate, or —O-triflate, in the presence or absence of a suitable base. Amine 5 may be further alkylated in the case where R2g is H to give disubstituted amine 6 where R2b is —NR2fR2g, wherein R2f and R2g are independently alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20), by treatement with an appropriate alkyl halide R2gX, where X is Cl, Br, I, —O-tosylate, —O-mesylate, or —O-triflate, in the presence or absence of a suitable base as above. Alternatively, amine 5 in which R2b is —NR2fR2g, wherein R2f is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20) may be prepared from amine 4 in which R2b is —NH2, by methods known to those skilled in the art, such as by treatment with an aldehyde or keto form of the formula R2f(R2f(O)) and a reductant (reductive amination) which include but are not limited to sodium borohydride, sodium cyanoborohydride, and hydrogen and a catalyst selected from palladium and platinum, and the like. Amine 5 may undergo further reductive amination in the case where R2g is H to give disubstituted amine 6 where R2b is —NR2fR2g, wherein R2f and R2g are independently alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20), by treatment with an aldehyde or keto form of the formula Rg2(R2g(O)) and a reductant as above. Alternatively, amine 5 in which R2b and/or R2c are —NR2fR2g wherein R2f is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl, or heteroaryl and R2g, is H, or amine 6, wherein R2b and/or R2c are —NR2fR2g, wherein R2f and R2g are independently alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl, or heteroaryl, may be prepared from glycopeptide antibiotic 2 in which R2b and/or R2c are bromine or iodine, by methods known to those skilled in the art, such as by palladium(0) mediated amination with an appropriate amine R2fNH2 or R2fR2gNH, respectively (J. F. Hartwig, Angew. Chem. Int. Ed. 1998, 37, 2046-2067, and references therein). embedded image

As shown in Scheme V, glycopeptide antibiotics 7 in which R2b is —NR2fR2g, wherein R2g is the group D-E-G, wherein D is —C(O)—, E is a single bond and G is H. alkyl(C1-C20), cycloalkyl(C3-C20), alkeny R(C2-C20), alkynyl (C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from amine 4 or amine 5 in which R2b is —NR2fR2g, where R2f is hereinbefore defined and R2g is H, by methods known to those skilled in the art. Such methods include employing any of a variety of acylation reactions using a carboxylic acid halide G-C(O)—Cl, carboxylic acid anhydride (G-C(O))2—O, or a carboxylic acid G-C(O)—OH in combination with an appropriate activating agent, such as 1,3-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate, 0-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 1,1′-carbonyldiimidazole, and the like, in the presence or absence of a suitable base to give glycopeptide antibiotics 7. embedded image

As described in Scheme VI, glycopeptide antibiotics 8 in which R2b is —NR2fR2g, where R2g is the group D-E-G as described above, wherein D is —C(S)—, E is a single bond and G is H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from glycopeptide antibiotics 7 in which D is —C(O)— by methods known to those skilled in the art such as by treatment with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide. embedded image

As described in Scheme VII, glycopeptide antibiotics 9 in which R2b is —NR2fR2g, wherein R2g is the group D-E-G, D is —S(O)2—, E is a single bond and G is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding primary amine 4 or secondary amine 5 in which R2b is —NR2fR2g, where R2f is hereinbefore defined and R2g is H, by methods known to those skilled in the art, such as by treatment with an appropriate sulfonic acid halide G-S(O)2—Cl or sulfonic acid anhydride (G-S(O)2)2O, in the presence or absence of a suitable base. embedded image

Glycopeptide antibiotics 10 in which R2b is —NR2fR2g, wherein R2g is the group wherein D is —C(O)—, E is —O— and G is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared as shown in Scheme VIII from primary amine 4 or secondary amine 5 in which R2b is —NR2fR2g, where R2f is hereinbefore defined and R2g is H, by methods known to those skilled in the art. Methods include treatment with an appropriate chloroformate G-O—C(O)—Cl, N-hydroxysuccinimide carbonate G-O—C(O)—OSu or, alternatively, by sequential treatment with phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with an alcohol G-OH, in the presence or absence of a suitable base to give glycopeptide antibiotics 10. embedded image

Glycopeptide antibiotics 11, in which R2b is —NR2fR2g, wherein R2g is the group D-E-G wherein D is —C(O)—, E is —NR2h— and G is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared as shown in Scheme IX from primary amine 4 or secondary amine 5 where R2b is NR2fR2g, where R2f is hereinbefore defined and R2g is H, by methods known to those skilled in the art. Methods include treatment with an appropriate isocyanate G-N═C═O or, alternatively, by sequential treatment with phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with a primary or secondary amine, G-NHR2h in the presence or absence of a suitable base to give glycopeptide antibiotics 11. embedded image

Glycopeptide antibiotics 12 in which R2b is —NR2fR2g, wherein R2g is the group D-E-G wherein D is —C(S)—, E is —O— and G is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared as shown in Scheme X from primary amine 4 or secondary amine 5 in which R2b is —NR2fR2g, where R2f is hereinbefore defined and R2g is H, by methods known to those skilled in the art. Methods include sequential treatment of primary amine 4 or secondary amine 5 with thiophosgene or a thiophosgene equivalent such as 1,1′-thiocarbonyldiimidazole or 1,1′-thiocarbonyl-bis(1,2,4)-triazole followed by treatment with an alcohol G-OH in the presence or absence of a suitable base to give glycopeptide antibiotics 12. embedded image

Glycopeptide antibiotics 13, in which R2b is —NR2fR2g, wherein R2g is the group D-E-G, D is —C(S)—, E is —NR2h— and G is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared as shown in Scheme XI from primary amine 4 or secondary amine 5 in which R2b is —NR2fR2g, where R2g is H and R2f is hereinbefore defined by methods known to those skilled in the art. Methods include treatment of primary amine 4 or secondary amine 5 with an appropriate isothiocyanate G-N═C═S or, alternatively, by sequential treatment with thiophosgene or a thiophosgene equivalent such 1,1′-thiocarbonyldiimidazole or 1,1′-thiocarbonyl-bis(1,2,4)-triazole followed by treatment with a primary or secondary amine G-NHR2h in the presence or absence of a suitable base to give glycopeptide antibiotics 13. embedded image

As shown in Scheme XII, glycopeptide antibiotics 14, wherein R2d is alkyl(C1-C20), alkenyl(C2-C20), alkynyl(C2-C20), aryl or heteroaryl, may be prepared from amine 4 in which R2b is —NH2 by methods known to those skilled in the art. Methods include treatment with an appropriate alkenyl-, alkynyl-, aryl- or heteroaryl-aldehyde R2d—CHO or aldehyde dialkyl-acetal R2d—CH(O-alkyl(C1-C20))2 and an excess of an oxidant, such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or it's equivalent to give glycopeptide antibiotics 14. embedded image

Glycopeptide antibiotics 15 wherein R2e is O, may be prepared as shown in Scheme XIII from an amine 4 by methods known to those skilled in the art. Methods include treatment of amine 4 with phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, in the presence or absence of a suitable base to give glycopeptide antibiotics 15. Alternatively, glycopeptide antibiotics 15 may be prepared from glycopeptide antibiotics 10, by treatment with a suitable base. embedded image

Glycopeptide antibiotics 16 wherein R2e is S, may be prepared as shown in Scheme XIV from amine 4, by methods known to those skilled in the art. Methods include treatment of amine 4 with thiophosgene or a thiophosgene equivalent such as 1,1′-thiocarbonyldiimidazole or 1,1′-thiocarbonyl-bis(1,2,4)-triazole, in the presence or absence of a suitable base to give glycopeptide antibiotics 16. Alternatively, glycopeptide antibiotics 16 may be prepared from glycopeptide antibiotics 12 in which G is aryl, by treatment with a suitable base. embedded image

Glycopeptide antibiotics 17 in which R2d is the group L-M, where L is —S— or —SCH2C(O)—, and M is as described above may be prepared as shown in Scheme XV from glycopeptide antibiotics 16 in which R2e is S, by methods known to those skilled in the art. Methods include treatment of glycopeptide antibiotics 16 with an appropriate alkylating agent M-X or M-C(O)—CH2—X, where X is Cl, Br, or I, in the presence or absence of a suitable base to give glycopeptide antibiotics 17. embedded image

As shown in Scheme XVI, glycopeptide antibiotics 18 in which R2d is the group L-M where L is —NH—, and M is as described above may be prepared from glycopeptide antibiotics 13 in which R2b is —NR2fR2g, wherein R2f is H and R2g is the group D-E-G where D is —C(S)—, E is —NR2h— and G is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl or heteroaryl by methods known to those skilled in the art. Methods include treatment of glycopeptide antibiotics 13 with a suitable mercury (II) salt, such a mercuric chloride, in the presence or absence of a suitable base to give glycopeptide antibiotics 18. embedded image

As shown in Scheme XVII, glycopeptide antibiotics 20, may be prepared from glycopeptide antibiotics 19, where R1a is H;

    • R2a is H or a moiety of the formulae: embedded image
      and R2b and R2c are H, by reduction under suitable reducing conditions which include hydrogenation under an atmosphere of hydrogen at pressures from about 1 to about 250 psi, over a suitable catalyst such as rhodium, either alone or adsorbed onto a suitable support such as carbon, alumina or diatomaceous earth in solvents such as water, methanol, ethanol, and the like, alone or in combination, in the presence or absence of a mineral or carboxylic acid, such as hydrochloric acid, sulfuric acid, or acetic acid, and the like, at temperatures from about 25° C. to the reflux temperature of the solvent to give glycopeptide antibiotics 20. The extent of the hydrogenation may be controlled by variations in the reaction temperature, hydrogen pressure, amount of catalyst, composition of the catalyst and support, amount of acid additive and the reaction time. embedded image embedded image

As described in Scheme XVIII, glycopeptide antibiotics 22, may be prepared from the corresponding glycopeptide antibiotics 21 as shown by methods known to those skilled in the art, such as by treatment with an aqueous mineral acid, such as hydrochloric acid, sulfuric acid, nitric acid, and the like, either alone or in a suitable solvent such as methanol, ethanol, water, N,N-dimethylformamide, dimethyl sulfoxide, and the like, at temperatures ranging from about 25° C. to about 90° C.

Alternatively, and when R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 are H, such compounds may also be prepared by treatment with α-mannosidase enzymes, such as purified α-mannosidase derived from sources such as Canavalia ensiformis or Prunus amygdalus or crude α-mannosidase present in jack bean meal or almond meal, in buffered aqueous systems, preferably in 0.1M sodium acetate buffer at about pH 3.5 to about 6.5, in the presence or absence of added metal salts, such as zinc chloride, and in the presence or absence of added cosolvents. embedded image

As described in Scheme XIX glycopeptide antibiotics 24, may be prepared from the corresponding glycopeptide antibiotics 23 by treatment with oc-mannosidase enzymes, such as purified ox-mannosidase readily derived from sources such as Canavalia ensiformis or Prunus amygdalus or crude α-mannosidase present in jack bean meal or almond meal, in buffered aqueous systems, preferably 0.1M sodium acetate buffer at pH about 3.5 to about 6.5, in the presence or absence of added metal salts such as zinc chloride, and in the presence or absence of added cosolvents. embedded image

Glycopeptide antibiotics 26 in which R5 is H, may be prepared as described in Scheme XX from the corresponding glycopeptide antibiotics 25 as shown in which R19, R20, R21 and R22 are H, by methods known to those skilled in the art, such methods include sequential treatment with sodium periodate, followed by a reductant such as sodium borohydride, followed by an aqueous mineral acid, such as hydrochloric acid, sulfuric acid, nitric acid, and the like, either alone or in a suitable solvent at temperatures ranging from about 25° C. to about 90° C. embedded image

As shown in Scheme XXI, glycopeptide antibiotics 27 in which R5 is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20) may be prepared from the corresponding glycopeptide antibiotics 26 in which R5 is H, by methods known to those skilled in the art, such as by alkylation with an appropriate alkylating agent R5—X, where X is Cl, Br, I, —O-tosylate, —O-mesylate, or —O-triflate, in the presence or absence of a suitable base. embedded image

Glycopeptide antibiotics 28, in which R5 is —C(O)—Y-Z, wherein Y is a single bond and Z is H, alkyl(C1-C20), cycloalkyl (C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared as shown in Scheme XXII from the corresponding compounds 26 in which R5 is H, by methods known to those skilled in the art, such as by employing any of a variety of acylation reactions using a carboxylic acid halide Z-C(O)—Cl, carboxylic acid anhydride (Z-C(O))2—O, or a carboxylic acid Z-C(O)—OH in combination with an appropriate activating agent, such as 1,3-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate, O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 1,1′-carbonyldiimidazole, and the like, in the presence or absence of a suitable base. embedded image

As described in Scheme XXIII glycopeptide antibiotics 29 in which R5 is —C(O)—Y-Z, wherein Y is —O— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 26 in which R5 is H, by methods known to those skilled in the art, such as by treatment with an appropriate chloroformate Z-O—C(O)—Cl or N-hydroxysuccinimide carbonate Z-O—C(O)—OSu, and the like, in the presence or absence of a suitable base. embedded image

Glycopeptide antibiotics 30 in which R5 is —C(O)—Y-Z, wherein Y is —NR8a— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared as shown in Scheme XXIV from the corresponding glycopeptide antibiotics 26 in which R5 is H, by methods known to those skilled in the art, such as by treatment with appropriate isocyanate Z-N═C═O, or, alternatively, by sequential treatment with phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with a primary or secondary amine, Z-NHR8a in the presence or absence of a suitable base. embedded image

As shown in Scheme XXV, glycopeptide antibiotics 31 in which R5 is as shown may be prepared from the corresponding glycopeptide antibiotics 26 in which R5 is H, by methods known to those skilled in the art, such as by treatment with aryl halides, tosylates, and triflates, such as a 2-chloropyrimidine, a 2-chlorobenzoxazole, a 2-chlorobenzothiazole, a 4-chlorobenzopyrimidine, a 2-fluoronitrobenzene, a 4-fluoronitrobenzene, and the like, in the presence or absence of a suitable base. embedded image embedded image

As shown in Scheme XXVI, glycopeptide antibiotics 33 in which R6a, R6b, R6c, R6d or R6e are independently alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20) may be prepared from the corresponding glycopeptide antibiotics 32 in which at least one of R6a , R6b , R6c , R6d and R6e are H, by methods known to those skilled in the art, such as by alkylation with an appropriate alkylating agent R6aX, R6bX, R6cX, R6dX or R6eX where X is Cl, Br, I, —O-tosylate, —O-mesylate, or —O-triflate, in the presence or absence of a suitable base. As recognized by those skilled in the art, the extent of alkylation may be controlled by the stoichiometry of the alkylating agent as well as variations in the reaction temperature, and reaction time. embedded image

As shown in Scheme XXVII, glycopeptide antibiotics 34 in which R6a, R6b, R6c, R6d or R6e are independently —C(O)—Y-Z, wherein Y is a single bond and Z is H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 32 in which at least one of R6a, R6b, R6c, R6d and R6e are H, by methods known to those skilled in the art, such as by employing any of a variety of acylation reactions using reagents such as a carboxylic acid halide Z-C(O)—Cl, carboxylic acid anhydride (Z-C(O))2—O, or a carboxylic acid Z-C(O)—OH in combination with an appropriate activating agent, such as 1,3-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate, O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 1,1′-carbonyldiimidazole, and the like, in the presence or absence of a suitable base. The extent of acylation may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image

As shown in Scheme XXVIII glycopeptide antibiotics 35 in which R6a, R6b, R6c, R6d or R6e are independently —C(O)—Y-Z, wherein Y is —O— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 32 in which at least one of R6a, R6b, R6c, R6d and R6e are H, by methods known to those skilled in the art, such as by treatment with reagents which include an appropriate chloroformate Z-O—C(O)—Cl or N-hydroxysuccinimide carbonate Z-O—C(O)—OSu, and the like, in the presence or absence of a suitable base. The extent of acylation may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image

Glycopeptide antibiotics 36 in which R6a, R6b, R6c, R6d or R6e are independently —C(O)—Y-Z, wherein Y is —NR8a— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), aryl or heteroaryl, may be prepared as shown in Scheme XXIX from the corresponding glycopeptide antibiotics 32 in which at least one of R6a, R6b, R6c, R6d and R6e are H, by methods known to those skilled in the art, such as by treatment with reagents which include an appropriate isocyanate Z-N═C═O, or, alternatively, by sequential treatment with reagents which include phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with a primary or secondary amine, Z-NHR8a in the presence or absence of a suitable base. The extent of acylation may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image

As shown in Scheme XXX, glycopeptide antibiotics 37 in which R6a, R6b, R6c, R6d and R6e are independently as shown may be prepared from the corresponding glycopeptide antibiotics 32 in which at least one of R6a, R6b, R6c, R6d and R6e are H, by methods known to those skilled in the art, such as by treatment with reagents which include appropriate aryl halides, tosylates, and triflates, such as a 2-chloropyrimidine, a 2-chlorobenzoxazole, a 2-chlorobenzothiazole, a 4-chlorobenzopyrimidine, a 2-fluoronitrobenzene, a 4-fluoronitrobenzene, and the like, in the presence or absence of a suitable base. The extent of alkylation may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As shown in Scheme XXXI, glycopeptide antibiotics 39 in which R7 is —C(O)—Y-Z, wherein Y is a single bond and Z is H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 38 in which R7 is H, by methods known to those skilled in the art, such as by employing any of a variety of acylation reactions using a carboxylic acid halide Z-C(O)—Cl, carboxylic acid anhydride (Z-C(O))2—O, or a carboxylic acid Z-C(O)—OH in combination with an appropriate activating agent, such as 1,3-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate, O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 1,1′-carbonyldiimidazole, and the like, in the presence or absence of a suitable base. embedded image

Glycopeptide antibiotics 40 in which R7 is —C(O)—Y-Z, wherein Y is —O— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared as shown in Scheme XXXII from the corresponding glycopeptide antibiotics 38 in which R7 is H, by methods known to those skilled in the art, such as by treatment with an appropriate chloroformate Z-O—C(O)—Cl or N-hydroxysuccinimide carbonate Z-O—C(O)—OSu or, alternatively, by sequential treatment with phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with an alcohol, Z-OH, in the presence or absence of a suitable base. embedded image

As shown in Scheme XXXIII glycopeptide antibiotics 41 in which R7 is —C(O)—Y-Z, wherein Y is —NR8a— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding compounds 38 in which R7is H, by methods known to those skilled in the art, such as by treatment with appropriate isocyanate Z-N═C═O or, alternatively, by sequential treatment with phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with an amine Z-NHR8a, in the presence or absence of a suitable base. embedded image

As shown in Scheme XXXIV glycopeptide antibiotics 42 in which R7 is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20), may be prepared from the corresponding glycopeptide antibiotics 38 in which R7 is H, by methods known to those skilled in the art, such as by alkylation with an appropriate alkylating agent R7—X, where X is Cl, Br, I, —O-tosylate, —O-mesylate, or —O-triflate, in the presence or absence of a suitable base. embedded image

Glycopeptide antibiotics 43 in which R7 is trialkylsilyl may be prepared from the corresponding glycopeptide antibiotics 38 as shown in Scheme XXXV in which R7 is H, by methods known to those skilled in the art, such as by treatment with an appropriate silylating agent, such as trimethylsilyl chloride, trimethylsilyl triflate, t-butyldimethylsilyl chloride, t-butyldimethylsilyl triflate, t-butyldiphenylsilyl triflate, and comparable silylating agents commonly used to protect alcohol functionality, in the presence or absence of a suitable base. embedded image

As shown in Scheme XXXVI glycopeptide antibiotics 45 in which R2a is as shown and R8, R9, R10R11, R12, R13, R14, R15, R16, R17 and R18 are independently —C(O)—Y-Z, wherein Y is a single bond and Z is H, alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 44 in which R2a is, as shown and at least one of R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 are H, by methods known to those skilled in the art, such as by employing any of a variety of acylation reactions using reagents such as a carboxylic acid halide Z-C(O)—Cl, carboxylic acid anhydride (Z-C(O))2—O, or a carboxylic acid Z-C(O)—OH in combination with an appropriate activating agent, such as 1,3-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate, O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 1,1′-carbonyldiimidazole, and the like, in the presence or absence of a suitable base. The extent of acylation may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As shown in Scheme XXXVII glycopeptide antibiotics 46 in which R2a is as shown and R8, R9, R10, R11R12, R13, R14, R15, R16, R17 or R18 are independently —C(O)—Y-Z, wherein Y is —O— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 44 in which R2a is as shown and at least one of R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 are H, by methods known to those skilled in the art, such as by treatment with reagents which include an appropriate chloroformate Z-O—C(O)—Cl or N-hydroxysuccinimide carbonate Z-O—C(O)—OSu or, alternatively, by sequential treatment with reagents such as phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with an alcohol Z-OH, in the presence or absence of a suitable base. The extent of reaction may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As shown in Scheme XXXVIII glycopeptide antibiotics 47 in which R is as shown and R8, R9, R10, R11, R12, R13, R14; R15, R16, R17 and R18 are independently —C(O)—Y-Z, wherein Y is —NR8a— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 44 in which R2a is as shown and at least one of R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 are H, by methods known to those skilled in the art, such as by treatment with reagents which include an an appropriate isocyanate Z-N═C═O or, alternatively, by sequential treatment with reagents which include phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with an amine Z-NHR8a, in the presence or absence of a suitable base. The extent of reaction may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As shown in Scheme XXXIX glycopeptide antibiotics 49 in which R8 and R9, R9 and R10, R10 and R11, R13 and R14, R15 and R16, R16 and R17, or R17 and R18 are independently joined forming moieties of the formula: embedded image
where n is an integer of from 1 to 3 may be prepared from the corresponding glycopeptide antibiotics 48 in which R8, R9, R10, R11, R12, R13, R14, R15, R16R17 and R18 are H, by methods known to those skilled in the art, such as by treatment with reagents which include phosgene or a phosgene equivalent reagent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, in the presence or absence of a suitable base. The extent of the reaction may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As shown in Scheme XL glycopeptide antibiotics 50 in which R8 and R9, R9 and R10, R10 and R11, R13 and R14, R15 and R16, R16 and R17, or R17 and R18are independently joined forming moieties of the formula: embedded image
where n is an integer of from 1 to 3 may be prepared from the corresponding glycopeptide antibiotics 48 in which at least one pair of R8 and R9, R9 and R10, R10 and R11, R13 and R14, R15 and R16, R16 and R17, or R17 and R18 are H, by methods known to those skilled in the art, such as by treatment with reagents which include an appropriate dialkyl acetal or dialkyl ketal of the formula R23R24—C(O-alkyl(C1-C20))2, such as a dimethyl acetal or dimethyl ketal, in the presence of a suitable acid catalyst, such as hydrochloric acid, p-toluene sulfonic acid mono-hydrate, camphor sulfonic acid, pyridinium p-toluene sulfonate, Amberlyst, or an equivalent mineral acid, carboxylic acid, or sulfonic acid commonly used by those skilled in the art. The extent of the reaction may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As shown in Scheme XLI, glycopeptide antibiotics 52 in which R8, R9, R10, R11, R13, R14, R15, R16, R17 or R18 are independently —(CH2)-alkenyl(C2-C20), —(CH2)-alkynyl(C2-C20), —(CH2)-aryl or —(CH2)-heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 51 prepared using the conditions described in Scheme XL (by treatment with a compound of the formula R23R24—C(O-alkyl(C1-C20))2 where R23 is H and R24 is alkenyl(C2-C20), alkynyl(C2-C20), aryl, or heteroaryl in which at least one pair of R5 and R9, R9 and R10, R10 and R11, R13 and R14, R15 and R16, R16 and R17, and R17 and R18 are moieties of the formula: embedded image
where R23 is H and R24 is alkenyl(C2-C20), alkynyl(C2-C20), aryl, or heteroaryl, and n is an integer of 1 to 3 by methods known to those skilled in the art, such as by treatment with a reductant and a protic acid or Lewis acid. Suitable combinations of reductants and acids include: sodium cyanoborohydride and trifluroacetic acid, sodium cyanoborohydride and hydrochloride acid, triethylsilane-trifluroacetic acid, borane-trimethylamine complex-aluminium chloride, borane-dimethylamine complex-boron trifluoride diethyl etherate, borane-dibutylboron triflate, or lithium aluminium hydride-aluminium chloride, and the like. embedded image embedded image

Alternatively, glycopeptide antibiotics 53 in which R2a is as shown and R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 or R18 are independently alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20) may be prepared as described in Scheme XLII from the corresponding glycopeptide antibiotics 44 in which R2a is as shown, and at least one of R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 are H, by methods known to those skilled in the art, such as by alkylation with an appropriate alkyling agent R8X, R9X, R10X, R11X, R12X, R13X, R14X, R15X, R16X, R17X and R18X, where X is Cl, Br, I, —O-tosylate, —O-mesylate, or —O-triflate, in the presence or absence of a suitable base. embedded image embedded image

As shown in Scheme XLIII, glycopeptide antibiotics 55 in which R19, R20, R21, or R22 are independently —C(O)—Y-Z, wherein Y is a single bond and Z is H, alkyl (C1-C20), cycloalkyl(C3-C20), alkenyl(C2-C20), alkynyl(C2-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 54 in which at least one of R19, R20, R21 and R22 are H, by methods known to those skilled in the art, such as by employing any of a variety of acylation reactions using reagents such as a carboxylic acid halide Z-C(O)—Cl, carboxylic acid anhydride (Z-C(O))2—O, or a carboxylic acid Z-C(O)—OH in combination with an appropriate activating agent, such as 1,3-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate, O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 1,1′-carbonyldiimidazole, and the like, in the presence or absence of a suitable base. The extent of acylation maybe controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image

As shown in Scheme XLIV glycopeptide antibiotics 56 in which R19, R20, R21 or R22 are independently —C(O)—Y-Z, wherein Y is —O— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 54 in which at least one of R19, R20, R21 and R22 are H, by methods known to those skilled in the art, such as by treatment with reagents which include an appropriate chloroformate Z-O—C(O)—Cl or N-hydroxysuccinimide carbonate Z-O—C(O)—OSu or, alternatively, by sequential treatment with reagents which include phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, and the like, followed by treatment with an alcohol Z-OH, in the presence or absence of a suitable base. The extent of acylation may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image

As described in Scheme XLV, glycopeptide antibiotics 57 in which R19, R20, R21 and R22 are independently —C(O)—Y-Z, wherein Y is —NR8a— and Z is alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20), alkynyl(C3-C20), perfluoroalkyl(C1-C6), aryl or heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 54 in which at least one of R19, R20, R21 and R22 are H, by methods known to those skilled in the art, such as by treatment with reagents which include an appropriate isocyanate Z-N═C═O or, alternatively, by sequential treatment with reagents such as phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylforrnate, and the like, followed by treatment with an amine Z-NHR8a in the presence or absence of a suitable base. The extent of acylation may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image

As shown in Scheme XLVI, glycopeptide antibiotics 58 in which R19 and R20, R20 and R21, R21 and R22 are independently joined forming moieties of the formula: embedded image
where n is an integer of 1 or 2 may be prepared from the corresponding glycopeptide antibiotics 54 in which at least one pair of R19 and R20, R20 and R21, and R21 and R22 are H, by methods known to those skilled in the art, such as by treatment with a reagent such as phosgene or a phosgene equivalent such as triphosgene, 1,1′-carbonyldiimidazole, 1,1′-carbonyl-bis(1,2,4)-triazole, or a chloronitrophenylformate, in the presence or absence of a suitable base. The extent of the reaction may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As shown in Scheme XLVII, glycopeptide antibiotics 59 in which R19 and R20, R20 and R21, or R21 and R22 are independently joined forming moieties of the formula: embedded image
where n is an integer of 1 or 2, may be prepared from the corresponding glycopeptide antibiotics 54 in which at least one pair of R19 and R20, R21 and R21, and R21 and R22 are H, by methods known to those skilled in the art, such as by treatment with a dialkyl acetal or dialkyl ketal of the formula R23R24—C(O-alkyl(C1-C20))2, such as a dimethyl acetal or dimethyl ketal, in the presence of a suitable acid catalyst, such as hydrochloric acid, p-toluene sulfonic acid mono-hydrate, camphor sulfonic acid, pyridinium p-toluene sulfonate, Amberlyst, or any equivalent mineral acid, carboxylic acid, or sulfonic acid commonly used by those skilled in the art. The extent of the reaction may be controlled by variations in reagent stoichiometry, reaction temperature, and reaction time. embedded image embedded image

As described in Scheme XLVIII, glycopeptide antibiotics 61 in which R19, R20, R21, and R22are independently —(CH2)-alkenyl(C2-C20), —(CH2)-alkynyl(C2-C20), —(CH2)-aryl or —(CH2)-heteroaryl, may be prepared from the corresponding glycopeptide antibiotics 60 prepared using the conditions described in Scheme XLVII (by treatment with a compound of the formula R23R24—C(O-alkyl(C1-C20))2 where R23 is H and R24 is alkenyl(C2-C20), alkynyl(C2-C20), aryl, or heteroaryl) in which at least one pair R19 and R20, R20 and R21, and R21 and R22 are moieties of the formula: embedded image
where R23is H and R24 is alkenyl(C2-C20), alkynyl(C2-C20), aryl, or heteroaryl, where n is an integer of 1 or 2, by methods known to those skilled in the art, such as by treatment with a reductant and a protic acid or Lewis acid. Suitable combinations of reductants and acids include: sodium cyanoborohydride and trifluroacetic acid, sodium cyanoborohydride and hydrochloride acid, triethylsilane-trifluroacetic acid, borane-trimethylamine complex—aluminium chloride, borane-dimethylarnine complex-boron trifluoride diethyl etherate, borane-dibutylboron triflate, or lithium aluminium hydride-aluminium chloride, and the like. embedded image

As described in Scheme XLIX, glycopeptide antibiotics 62 in which R19, R20, R21 and R22 are independently alkyl(C1-C20), cycloalkyl(C3-C20), alkenyl(C3-C20) or alkynyl(C3-C20) may be prepared from the corresponding compounds 54 in which at least one of R19, R20, R21 and R22 are H, by methods known to those skilled in the art, such as by alkylation with an appropriate alkylating agent R19X, R20X, R21X or R22X, where X is Cl, Br, I, —O-tosylate, —O-mesylate, or —O-triflate, in the presence or absence of a suitable base. The extent of the reaction may be controlled by variations in the stoichiometry of the alkylating agent, reaction temperature, and reaction time. embedded image

As described in Scheme XLX glycopeptide antibiotics 64 wherein R2 and R2a are as shown may be prepared by fermentation of glycopeptide antibiotics 63 wherein R2 and R2a are as shown in the presence of modified strains of Streptomyces hygroscopicus and in particular, strain LL4780. embedded image embedded image

Generally, reactions described herein may be conducted in a solvent or solvents which are compatible with the reaction conditions contemplated, as is known by those skilled in the art, which include but are not limited to water, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, N,N-dimethyl propyleneurea, N-methylpyrrolidinone, and the like, at temperatures ranging from −15° C. to the reflux temperature of the solvent.

Additionally, reactions are performed in a solvent appropriate to the reagents and materials employed and suitable for the transformation being effected. Various functionalities present on the molecule must be consistent with the chemical transformations proposed. This may necessitate judgement as to the order of synthetic steps and that substituents on the starting materials may be incompatible with some of the reaction conditions. Such restrictions to the substituents which are compatible with the reaction conditions will be apparent to one skilled in the art.

Suitable bases employed in the reactions as described in Schemes IV-XI, XIII-XVI, XXI-XXXIX, and XLII-XLVI include but are not limited to amine bases such as ammonia, triethylamine, N,N-diisopropylethylamine, pyridine, 2,6-di-tert-butyl pyridine, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, and the like, carbonate bases such as sodium carbonate, potassium carbonate, cesium carbonate, and the like, hydroxide bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, barium hydroxide, and the like, or hydride bases such as sodium hydride, potassium hydride, calcium hydride, and the like.

Reactions may be monitored by reverse-phase thin-layer chromatography, electrospray mass spectrometry, analytical high-pressure liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), and/or other analytical methods commonly employed by those skilled in the art.

Reaction products may be isolated by the removal of heterogeneous materials, if present, in the reaction vessel by filtration, followed by the removal of solvent by evaporation and/or by direct precipitation of the crude product upon addition of sufficient quantities of a co-solvent in which the product is minimally soluble, such as acetonitrile, acetone, methanol, ethanol, ethyl acetate, diethyl ether, and the like, followed by filtration or centrifugation.

Reaction products may be purified by reverse-phase preparative TPLC over commonly marketed reverse phase supports, such as the C18-coated silica ODS packing support marketed by the YMC corporation (currently a wholly-owned subsidiary of the Waters corporation), employing isocratic elution conditions, gradient elution conditions, or a combination of both isocratic and gradient elution conditions, using mixed solvent systems consisting of an organic solvent, such as methanol, acetonitrile, and the like, and water, and containing approximately 0.005-0.01% by volume of trifluoroacetic acid, or, alternatively, approximately 0.01-0.05% by volume of acetic acid. In those instances wherein the isolated product exhibits limited stability in the acidic media of the elution solvents, such as those cases in which the product(s) is a (are) ketal(s) or aryl-acetal(s), it is advantageous to employ 0.01% of acetic acid and to neutralize the product-containing fractions to pH 6 (pH paper) by the addition of sufficient quantities of aqueous ammonium hydroxide. Excess ammonium acetate thus produced is removed from the final desired product following concentration of the product-containing fractions in vacuo, by lyophilization, or by washing with a solvent in which the product is minimally soluble, such as ethanol, 2-propanol, and the like.

Typically dialkyl acetals or dialkyl ketals of the formula R23R24—C(O-alkyl(C1-C2O))2, used in the hereinbefore described schemes include the dimethyl acetals of acetaldehyde, propionaldehyde, butyraldehyde, 3-methylbutyraldehyde, 3,3-dimethylbutyraldehyde, cyclopentanecarboxaldehyde, cyclohexanecarboxaldehyde, 2-ethyl-butyraldehyde, phenylacetaldehyde, 4-methoxyphenylacetaldehyde, 4-bromophenylacetaldehyde, 3-phenyl-propionaldehyde, 2-(N-benzyloxycarbonyl-4-piperidinyl)-acetaldehyde (prepared in two steps from 2-(4-piperidnyl)-ethanol by N-funtionalization and oxidation), 1-adamantylcarboxaldehyde, benzaldehyde, 3-(4-methylphenoxy)-benzaldehyde, 3-nitro-4-methoxy-benzaldehyde, 4-benzyloxybenzaldhyde, 3-benzyloxybenzaldhyde, 4-carboxymethylbenzaldehyde, 4-(2-propyl)benzaldehyde, 4-(1-propyl)benzaldehyde, 4-phenylbenzaldehyde, piperonal, 1-naphthaldehyde, 2-naphthaldehyde, 6-methoxy-2-naphthaldehyde, 4-methoxy-1-naphthaldehyde, and the like, and the dimethyl ketals of acetone, cyclopentanone, cyclohexanone, 2-methylcyclohexanone, 4-tert-butylcyclohexanone, 2,2-dimethylcyclohexanone, 2,5-dimethylcyclohexanone, 3,3,5,5-tetramethylcyclohexanone, 2-adamantanone, bicyclo[3.3.1]nonan-9-one, tetrahydrothiopyran-4-one, acetophenone, 4-fluoroacetophenone, (R)-camphor, (S)-camphor, carvone, and the like.

In those instances where the parent aldehyde or ketone is not commercially available, the aldehyde or ketone is prepared from readily accessible compounds by methods known to those skilled in the art, such as by oxidation of the corresponding alcohols, by Kornblum-type oxidation of the corresponding alkyl- or benzyl-bromides, by oxidation of aryl methanes, by benzylic bromination of aryl methanes followed by Kornblum oxidation of the resultant benzyl bromide or hydrolysis of the resultant benzylic dibromides, by reduction of the corresponding esters, carboxylic acids, or nitriles, or, in the case of alkoxy-substituted benzaldehydes, by alkylation of commerically available phenolic benzaldehydes or an appropriate precursor thereof, or, in the case of aryl- or heteroaryl-substituted benzaldehydes, by palladium-mediated couplings of bromo- or iodo-substituted benzaldehydes or an appropriate precursor thereof with aromatic or heteroaromatic boronic acids, or, in the case of acyl-substituted benzaldehydes, by Friedel-Crafts acylation of a benzaldehyde or an appropriate precursor thereof.

Aldehydes or ketones used in these reactions are easily converted to their corresponding dialkyl-acetals, typically dimethylacetals, by methods known to those skilled in the art, such as by reaction of the aldehyde or ketone with trimethylorthoformate (to prepare dimethyl acetals) in the presence of an acid catalyst, such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, camphorsulfonic acid, immobilized sulfonic acid resins (anionic exchange resins) and the like, or, by reaction of the aldehyde or ketone with an alcohol in the presence of an acid catalyst such as those listed above while employing the use of a dehydrating agent such as molecular sieves or by employing the use of a Dean-Stark apparatus, or employing any other conditions that permit the efficient removal of water from the reaction.

Biological Activity

Methods for In Vitro Antibacterial Evaluation (Table 1)

The minimum inhibitory concentration (MIC), the lowest concentration of the antibiotic which inhibits growth of the test organism, is determined by the broth dilution method using Muller-Hinton II agar (Baltimore Biological Laboratories) following the recommendations of the National Committee for Clinical Laboratory Standards [Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, approved standard M7-A2, National Committee for Clinical Laboratory Standards, Villanova, Pa.].

An inoculum level of 5×105 CFU/mL, and a range of antibiotic concentrations (64-0.06 μg/mnL) is used. The MIC is determined after the microtiter plates are incubated for 18 hours at 35° C. in an ambient air incubator. The test organisms include a spectrum of Gram-positive bacteria comprised of Staphylococcus sp., Streptococcus sp. and Enterococcus sp. These organisms include recent clinical isolates that are resistant to methicillin, penicillin and/or vancomycin. The results of representative examples of the invention are given in Table 2.

TABLE 2
StaphylococcusStaphylococcus
EXAMPLEaureusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBER(GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 3>128>128>128>128>128>128
Example 12>128>128>128>128>128>128>128>128
Example 136464646464646464
Example 14>128>128>128>128>128>128>128>128
Example 15>128>128>128>128>128>128>128>128
Example 161281281286412812832128
Example 17>64>64>64>64>64>64>64>64
Example 18>128>128>128>128>128>128>128>128
Example 19>128>128>128>128>128>128>128>128
Example 22>128>128>128>128>128>128>128>128
Example 24>64>64>64>64>64>64>64>64
Examp1e 25>128>128>128>128>128>128>128>128
Example 261616163216163232
Example 2716168168888
Example 2884488848
Example 2988888888
Example 3081616168888
Example 31161616168161616
Example 3222422224
Example 33416888488
Example 343216323232163232
Example 3588888888
Example 36>128>128>128>128>128>128>128>128
Example 378888881616
Example 383264646464643264
Example 39161681616161616
Example 406464646464323264
Example 41>64>64>64>64>64>64>64>64
Example 4228422224
Example 446464326464161664
Example 45888168888
Example 4688888888
Example 473232161616161616
Example 481616161616161632
Example 4944444428
Example 513232643232323232
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 3>128>128>128>128128>128128
Example 12>128>128>128>128>128>128>128
Example 1364646464326432
Example 14>128>128>128>128>128>128>128
Example 15>128>128>128>128>128>128>128
Example 1664816324328
Example 17>64>6464>6432>6464
Example 18>12812812812864>128128
Example 19>128>128>128>128128>128>128
Example 22>128>128>12812864>128128
Example 24>64646464>64>6432
Example 25>128>128>128>128>128>128>128
Example 261648164164
Example 278488884
Example 284484442
Example 298444284
Example 3084841684
Example 311688816164
Example 322221242
Example 334444184
Example 3416816164328
Example 358888882
Example 36>128646412864>12864
Example 3788168884
Example 3864163232646416
Example 3916888484
Example 4064161632163216
Example 41>646464>643264
Example 422221141
Example 4432646482168
Example 458448484
Example 46484824
Example 47881620.58
Example 4816848416
Example 49214214
Example 5132321616464
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 5216163216816816
Example 5342442422
Example 53a>128>128>128>128>128>128>128>128
Example 54>128>128>128>128>128>128>128>128
Example 54a>128>128>128>128>128>128>128>128
Example 5881632161616816
Example 59>128>128>128>128>128>128>128>128
Example 60>128>128>128>128>128>128>128>128
Example 60a>128>128>128>128>128>128>128>128
Example 6l>128>128128>128>128>128>128>128
Example 62>128>128>128>128>128>128>128>128
Example 64>128>128>128>128>128>128>128>128
Example 65>128>128>128>128>128>128>128>128
Example 66168888848
Example 66a>128>128>128>128>128>128>128>128
Example 67>128>128>128>128>128>128>128>128
Example 69>128>128>128>128>128>128>128>128
Example 72>128>128>128>128>128>128>128>128
Example 73>128>128>128>128>128>128>128>128
Example 74>128>128>128>128>128>128>128>128
Example 764-82-82-82-42-84-82-82-8
Example 77168-16164-88-161688-16
Example 7888848888
Example 7984444844
Example 803232643232323232
Example 8l>128>128>128>128>128>128>128>128
Example 82168168161688
Example 8344424422
Example 8488848888
Example 896464646464646464
Example 92>128>128>128>128>128>128>128>128
Example 93>128>128>128>128>128>128>128>128
Example 94>64>64>64>64>64>64>64>64
Example 95>64>64>64>64
Example 95a4844
Example 95b1211
Example 96c0.50.5110.51
Example 96>128>128>128>128>128>128
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 521648848
Example 53212212
Example 53a>128>128>128>128>128>128
Example 54>128>128>128>128>128>128
Example 54a>128128128>128>128>128
Example 58444448
Example 59>128>128>128>128>128>128>128
Example 60>128>128>128>128>128>128>128
Example 60a>128>128>128>128>128>128>128
Example 61>128>128128>128128>128>128
Example 62>128>128>128>128>128>128>128
Example 64>128>128>128>128>128>128>128
Example 65>128>128>128>128>128>128
Example 668448484
Example 66a>128>128>128>128>128>128
Example 67>128>128128>128>128>128>128
Example 69>128>128>128>128>128>128>128
Example 72>128>128>128>128>128>128>128
Example 73>128>128>128>128>128>128>128
Example 74>128>128>128>128>128>128>128
Example 761-42-42-42-42-42-80.5-2
Example 7784-8444-882
Example 784444882
Example 794444244
Example 803232323232328
Example 81>128>128>128>128>128>128>128
Example 82844448
Example 83222122
Example 844444442
Example 8964323264646432
Example 92>128>128>128>128>128>128
Example 93>128>128>128>128>128>128
Example 94>64>64>64>64>64>64
Example 95>64>64>64
Example 95a844
Example 95b211
Example 96c0.50.510.25110.5
Example 96>128>128>128>128>128>128128
StaphylococcusStaphylococcus
EXAMPLEaureusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBER(GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 96a>128128>128>128>128>128
Example 96b212211
Example 97>64>64>64>64
Example 97a2210.5
Example 97b1110.5
Example 98b1616168
Example 98c2422
Example 99b444444
Example 99c221211
Example 100b2222
Example 100c1111
Example 101448844
Example 101a424442
Example 102211-21-20.5-11-20.5-11-2
Example 10321222212
Example 10421110.510.5-11
Example 104a0.5-640.50.50.5-320.50.50.50.5-64
Example 104b0.50.50.50.50.50.50.50.5
Example 1050.25-10.5-11-2<0.5-10.5-10.25-2<0.5-1<0.5-1
Example 1060.5-20.5-20.5-20.5-20.25-10.25-20.5-20.5-2
Example 106a22222422
Example 106b8881681688
Example 107221211
Example 108111111
Example 109111111
Example 110111211
Example 111111111
Example 1120.5-1110.5-21-21
Example 11321111211
Example 11422221222
Example 11511110.510.51
Example 11611110.5111
Example 11721211211
Example 118<0.5-1<0.5-11<0.5-1<0.5-1<0.5-1<0.5-1<0.5-1
Example 11911211111
Example 120<0.5<0.51<0.5<0.5<0.5<0.5<0.5
Example 12121111221
Example 12222222122
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 96a>128128128>1286412864
Example 96b2110.50.520.5
Example 97>64>64>64
Example 97a422
Example 97b111
Example 98b1688
Example 98c211
Example 99b4444282
Example 99c1111121
Example 100b211
Example 100c111
Example 1014422181
Example 101a8111121
Example 1020.5-10.5-110.5-10.5-11-20.5
Example 1031121121
Example 1040.5-10.510.5-10.510.5
Example 104a0.5-64323216-3216-323216
Example 104b0.50.544482
Example 1050.25-1<0.5-10.5-1<0.5-10.5-1<0.5-10.5-1
Example 1060.25-10.5-10.5-20.25-1<0.12-10.25-10.25
Example 106a222112
Example 106b848448
Example 1071111111
Example 108111<0.5111
Example 109111<0.5111
Example 1101111111
Example 111110.510.511
Example 1120.5-110.5-10.5-10.5-10.5-110.5
Example 1131110.5110.5
Example 1142121221
Example 11510.510.5110.5
Example 11610.511110.5
Example 1171111120.5
Example 118<0.5-1<0.5-<0.5<0.5-10.25-0.25<0.5-<0.5<0.5-10.25-0.25
Example 119111111<0.5
Example 120<0.5<0.51<0.5<0.5<0.5<0.5
Example 1211110.50.521
Example 1222221121
StaphylococcusStaphylococcus
EXAMPLEaureusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBER(GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 12388844888
Example 12422221222
Example 125323232832323232
Example 12688888888
Example 12742242422
Example 12842222422
Example 12922222224
Example 1303232323232323232
Example 13222422424
Example 13321412211
Example 13511111211
Example 136161632816161616
Example 13721-22-41-21-222-41-2
Example 137a3232321632323232
Example 137b161616816161616
Example 13822222222
Example 14011<0.5111<0.51
Example 141>64>64>64>64>64>64>64>64
Example 1432-42-44-82-41-42-82-42-4
Example 1441110.50.5412
Example 145<0.511<0.5<0.5111
Example 14688884888
Example 147<0.5-<0.50.50.5<0.5-<0.50.5-10.5-10.5-1<0.5-<0.5
Example 14922422222
Example 15042822222
Example 150a3232321632321632
Example 151881648848
Example 152161632161616816
Example 15322422222
Example 15411211211
Example 155<0.5-<0.50.50.5<0.5-<0.5<0.5-<0.5<0.5-<0.50.5-1<0.5-<0.5
Example 15622422222
Example 1573216321632321632
Example 15821211222
Example 16188844844
Example 1621632161616161616
Example 16348844444
Example 1644168816848
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 1234884484
Example 1242221121
Example 12532323232323232
Example 1268888888
Example 127224212
Example 1282242242
Example 1292221141
Example 13032323232163232
Example 1322121121
Example 133111<0.5111
Example 13510.510.50.510.5
Example 1361616884324
Example 1371-211-20.5-20.5-11-21
Example 137a16161688168
Example 137b8884884
Example 1381241122
Example 14011<0.5<0.5<0.5<0.5<0.5
Example 141>64>64>64>64>64>64>64
Example 1432-40.5-21-21-212-41-2
Example 1441110.250.120.50.25
Example 145<0.5<0.51<0.51<0.50.5
Example 1468884484
Example 1470.5-11-21-2<0.5-1<0.5-1121
Example 1492111111
Example 1502121121
Example 150a16161688328
Example 1518244282
Example 15288888168
Example 1531110.50.520.5
Example 1541120.50.2521
Example 155<0.5-<0.5<0.5-1<0.5-2<0.5-1<0.5-1<0.5-11<0.5
Example 1562221121
Example 15716161688324
Example 15820.521121
Example 1614442282
Example 1621616168888
Example 1631481422
Example 16444410.541
StaphylococcusStaphylococcus
EXAMPLEaureusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBER(GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 164a888816888
Example 1651632161616161616
Example 166888
Example 167161616816161616
Example 16811111211
Example 1693232>643232323232
Example 17044124244
Example 17284442844
Example 17320.510.50.5221
Example 17412222112
Example 17544444444
Example 17722222222
Example 178484888416
Example 1793232323232323232
Example 18021222222
Example 18144444444
Example 182>64>64>64>64>64>64>64>64
Example 18382284444
Example 1843232323232323232
Example 185>64>64>64>64>64>64>64>64
Example 18622221222
Example 1876464326464646464
Example 19016161684161616
Example 19188844844
Example 19241222221
Example 193110.50.50.2510.50.5
Example 1941110.50.5210.5
Example 1950.50.50.50.50.50.50.50.5
Example 196>64>64>6464>64>6464>64
Example 1971664641664323232
Example 19810.50.50.50.250.50.50.5
Example 19921221212
Example 20021211211
Example 2010.250.50.50.50.250.250.250.25
Example 20244844444
Example 20322411211
Example 20484844844
Example 20522222222
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 164a8484484
Example 16516161688168
Example 16644444
Example 1671616888168
Example 16810.520.50.51
Example 1693232323216>648
Example 1704841211
Example 1728882242
Example 1730.5120.50.250.50.5
Example 1741220.5110.5
Example 1754482242
Example 1772241241
Example 17848320.5242
Example 17932323232163232
Example 1802221110.5
Example 1814882122
Example 182>64>64>64>64>64>64>64
Example 1834842442
Example 18432323216323216
Example 185>64>64>64>64>64>64>64
Example 1862121120.5
Example 1876412812816643232
Example 19048888168
Example 1914484444
Example 1922121142
Example 1930.50.510.250.250.50.25
Example 1940.50.510.50.510.5
Example 1950.5242142
Example 196>6432326464>6464
Example 19716323288164
Example 1980.50.51<0.120.50.5
Example 1991120.50.51
Example 200112112
Example 2010.50.250.250.250.250.25
Example 2024222442
Example 2032121121
Example 204424424
Example 205222112
StaphylococcusStaphylococcus
EXAMPLEaureusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBER(GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 20611111111
Example 20722111111
Example 20884484844
Example 209224
Example 2103232323232323232
Example 210a48448844
Example 21242422422
Example 214132221122
Example 2150.50.510.50.50.510.5
Example 21622211212
Example 21744844844
Example 21844444444
Example 21942222824
Example 22011110.510.50.5
Example 22122122221
Example 222>64>64>64>64>64>64>64>64
Example 223>6464>6464646464>64
Example 22442414422
Example 22584848844
Example 226161616816161616
Example 227128128>128128128128128128
Example 2283232323232323232
Example 229>128>128>128>128>128>128>128>128
Example 229a>128>128>128>128>128>128>128>128
Example 229b>128>128>128>128>128>128>128>128
Example 23022212212
Example 230a0.5-21-21-20.5-20.25-21-20.5-11-2
Example 230b42221422
Example 230c12812812864>128128128128
Example 2312-41-21-21-42-42-41-41-4
Example 231a1-211-21-20.5-12-41-21-2
Example 231b4-644-648-644-324-324-644-324-64
Example 231c22222221
Example 23244844444
Example 23422222222
Example 2351-20.5-21-20.5-10.5-21-21-20.5-1
Example 23622224222
Example 23742428424
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 20610.510.50.51
Example 2071110.50.54
Example 2084444444
Example 20914112
Example 2103232323283232
Example 210a4844244
Example 2122222221
Example 2140.51110.51
Example 215<0.120.50.50.5<0.120.5
Example 2162121121
Example 217224128
Example 2184444484
Example 2192222241
Example 22010.250.50.250.250.5
Example 221222112
Example 222>64>64>64>64>64>64
Example 223646464646464
Example 224212112
Example 225444224
Example 22688881682
Example 22712864324328
Example 228321616161616
Example 229>128>128>128>128>128>128>128
Example 229a>128>128>128>128>128>128>128
Example 229b>128>128>128>128>128>128>128
Example 2301110.5120.5
Example 230a0.5-20.25-10.5-20.12-0.50.12-0.50.25-10.25-0.5
Example 230b2121121
Example 230c64646464646432
Example 23121-41-20.5-10.25-0.510.5-1
Example 231a1110.12-0.25<0.12-0.250.50.5
Example 231b4-644-324-322-322-168-321-32
Example 231c1120.50.510.5
Example 2324222142
Example 23421110.521
Example 2350.5-10.25-0.50.5-10.25-0.50.25-0.50.5-10.25-0.5
Example 2362220.50.521
Example 2372121141
StaphylococcusStaphylococcus
EXAMPLEaureusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBER(GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 23844844824
Example 23921242222
Example 239a42444444
Example 24040.5412444
Example 24122222222
Example 241a22222422
Example 24288844848
Example 2436464646464646464
Example 243a3232323232323232
Example 244881681888
Example 24584444844
Example 245a42222222
Example 245b16161681616816
Example 245c>128128>128128128128128128
Example 24684444844
Example 246a41211222
Example 246b128641286464646464
Example 246c>128>128>128>128>128>128>128>128
Example 2483264643264323232
Example 2491281281281286464128128
Example 251>64>64>64>64>64>64
Example 251a>646464>6464>64
Example 251b88816816
Example 253>64>64>6464>64>6464>64
Example 253a42444424
Example 253b42824424
Example 254444484
Example 254b448888
Example 255>0.50.50.50.50.50.50.5>0.5
Example 255a>0.50.50.5>0.5>0.5>0.5>0.5>0.5
Example 256>64>64>64>64>64>64
Example 256a>64>64>64>64>64>64
Example 2570.50.50.50.50.50.50.50.5
Example 257a0.50.50.50.50.50.50.50.5
Example 257b0.50.50.50.50.50.50.50.5
Example 261a>64>64>64>64>64>64
Example 261b1616168168
Example 261c888888
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 2384222241
Example 2392121121
Example 239a2221222
Example 2402242222
Example 2412221242
Example 241a2242141
Example 24284844162
Example 24364646432326432
Example 243a32323232163216
Example 2444442242
Example 2454442182
Example 245a21210.521
Example 245b16888284
Example 245c1281281281286412864
Example 2464444482
Example 246a1111122
Example 246b641286464326464
Example 246c>128>128>128>128>128>128>128
Example 24832161632323216
Example 2491281286412812864128
Example 251>64>64>64>64>64>6464
Example 251a6464646432>6416
Example 251b88884164
Example 2536464646464>6432
Example 253a2444181
Example 253b2242242
Example 2544444242
Example 254b4882442
Example 2550.5323264326432
Example 255a>0.56464>6464>6464
Example 256>64>64>64>64>64>64>64
Example 256a>64>64>64>64>64>6464
Example 2570.5222281
Example 257a0.58888324
Example 257b0.5222241
Example 261a>64>64>64>64>64>64
Example 261b888448
Example 261c8444416
StaphylococcusStaphylococcus
EXAMPLEaureusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBER(GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 262a12864>128646464
Example 262b422424
Example 263646464>646464
Example 264a1616168816
Example 264b888848
Example 265a32161681616
Example 265b32888816
Example 270a444444
Example 270b888848
Example 271a448844
Example 277a>128>128>128>128>128>128>128>128
Example 277b>64>64>64>64>64>64>64>64
Example 278b84888848
Example 278c82844444
Example 279a>64>64>64>64>64>64>64>64
Example 280a>128>128>128>128>128>128>128>128
Example 280b>128128>12812812812864128
Example 282>128>128>128>128>128>128>128>128
Example 283a64641286464646464
Example 283b64641281286412864128
Example 283c3232643232321632
Example 284b>128>128>128>128>128>128>128>128
Example 287>64>64>64>64>64>64>64>64
Example 296>128>128>128>128>128>128>128>128
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 262a6464646416128
Example 262b122112
Example 263323264321664
Example 264a8884416
Example 264b844448
Example 265a888848
Example 265b888448
Example 270a422224
Example 270b444444
Example 271a844244
Example 277a>128>128>128>128>128>128
Example 277b>64>64>64>64>64>64>64
Example 278b8444282
Example 278c4242282
Example 279a>646464>6464>6464
Example 280a>128128128>128128>128128
Example 280b6432321283212832
Example 282>128>128>128>128>128>128
Example 283a646464643264
Example 283b646464646464
Example 283c16161681632
Example 284b>128>128>128>128>128>128
Example 287>64>64>64>64>64>64>64
Example 296>128>128>128>128>128>128
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 3>128>128>128>128
Example 12128128128>128>128>128>128>128
Example 1316244864>64>64
Example 1412812864>128>128>128>128>128
Example 1512812864>128>128>128>128>128
Example 16646412812816>128>128>128
Example 17>6464>64>64>64>64>64>64
Example 1812864128128128>128>128>128
Example 19>12864128128>128>128>128>128
Example 223288832>128>128>128
Example 24>6464>64>646464>64>64
Example 25>128128>128>128>128>128>128>128
Example 26161632328643264
Example 27323216168323232
Example 2844441488
Example 293232323216323264
Example 308161684323264
Example 313232641686464128
Example 32161616168488
Example 333232643216161632
Example 34321632328323232
Example 35881682161632
Example 36>128128>128>128128>128>128>128
Example 37161616324161616
Example 383232643232128128>128
Example 391681684161616
Example 4064321286432128128>128
Example 416464>6464326464>64
Example 4281616848816
Example 4416163284161632
Example 45161632164163232
Example 468888181632
Example 472284143232
Example 4816832168646464
Example 4948882161632
Example 5116488864>64>64
Example 52881688323232
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 3>128>128>128>128>128>128>128>128
Example 12>128>128>128>128>128>128>128>128128
Example 13>6464>64>64>6464646464
Example 14>128>128>128>128>128>128>128>128128
Example 15>128>128>128>128>128>128>128>128128
Example 16>12864>128>128>128128>12816128
Example 17>64>64>64>64>64>64646464
Example 18>128128>128>128>128>128>12864128
Example 19>128128>128>128>128>128>128128128
Example 22>128>128>128>128>128>128>12864>128
Example 24>6432>64>646464643264
Example 25>128>128>128>128>128>128>128128128
Example 2664326432323264832
Example 2764163232323264816
Example 28848888844
Example 2964163232321664816
Example 3064166432643264816
Example 3112816128646432448
Example 32884484824
Example 33161616163286448
Example 3432323264643264816
Example 3532832161683248
Example 36>128128>128>128>128>128>128128128
Example 3716416161681648
Example 38128641281281281281283264
Example 3916832161683288
Example 40>12864>128128128641281664
Example 41646464>646464326464
Example 428888841624
Example 4416832161683284
Example 451616161632163248
Example 46841616841684
Example 47164643284842
Example 486416646464166448
Example 49241616168824
Example 51>64>64>64>64>64>64>641664
Example 5232166432641632832
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 5311411888
Example 53a6432646464>128>128>128
Example 54>128128>128>128>128>128>128>128
Example 54a>128128>128>128>128>128>128>128
Example 581681688646464
Example 59>12864128128>128>128>128>128
Example 60>12864128128>128>128>128>128
Example 60a>12864128>128>128>128>128>128
Example 611286464128128128128128
Example 62>12864128128>128>128>128>128
Example 64128128>128>128>128>128>128>128
Example 65>128128128128128>128>128>128
Example 663232643216163232
Example 66a>128>128>128>128>128>128>128>128
Example 6712864128128128128128128
Example 69128128128128>128>128>128>128
Example 7212816646464>128>128>128
Example 73>12864128128>128>128>128>128
Example 74128128>128>128>128>128>128>128
Example 760.25-2<0.06-0.250.25-4<0.12-10.25-24-164-164-32
Example 7710.25-0.52-421161616
Example 7810.25210.5161616
Example 794884416832
Example 80841688326464
Example 81128128>128>128>128>128>128>128
Example 820.50.25221161616
Example 830.25<0.120.250.50.25444
Example 8410.12110.5888
Example 8932481632646464
Example 92>128128128128>128>128>128>128
Example 93>128128>128>128>128>128>128>128
Example 94>64>64>64>64>64>64>64>64
Example 95>64
Example 95a16
Example 95b8
Example 96c<0.06<0.06<0.061
Example 96>128>128>128>128
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 538416482824
Example 53a>128>128>128>128>128>128>128>128>128
Example 54>128>128>128>128>128>128>128128128
Example 54a>128>128>128>128>128>128>128128128
Example 5864326464643264832
Example 59>128>128>128>128>128>128>128128128
Example 60>128128>128>128>128>128>128128128
Example 60a>128128>128>128>128>128>128128128
Example 61128128128128128>12812812864
Example 62>128128>128>128>128>128>12864128
Example 64>128>128>128>128>128>128>128>128128
Example 65>128128>128>128>128128>128128128
Example 6632864321683244
Example 66a>128>128>128>128>128>128>128>128128
Example 67128128>128128128>128>12812864
Example 69>128>128>128>128>128>128>128128128
Example 72>12864>128>128>128>128>12812864
Example 73>128>128>128>128>128>128>128128128
Example 74>128>128>128>128>128>128>128128128
Example 764-164-84-324-164-162-84-161-22-8
Example 7716816-3216168161-24
Example 78881616881624
Example 79324168883242
Example 80643264646432641632
Example 81>128128>128>128>128>128>128128128
Example 8216832161681624
Example 83424442412
Example 848816884818
Example 89646464646464643232
Example 92>128128>128>128>128>128>128128128
Example 93>128>128>128>128>128>128>128128128
Example 94>64>64>64>64>64>64>64>64>64
Example 95>64>64
Example 95a3232
Example 95b84
Example 96c22222212
Example 96>128>128>128>128>128>128128>128
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 96a321632>128
Example 96b0.25<0.120.254
Example 97>64
Example 97a4
Example 97b2
Example 98b64
Example 98c8
Example 99b2<0.5116
Example 99c<0.5<0.5<0.54
Example 100b8
Example 100c2
Example 1012<0.5216
Example 101a1<0.518
Example 102<0.12-0.25<0.06<0.12-<0.12<0.06<0.12-0.252-42-42-4
Example 1030.50.120.120.120.25488
Example 104<0.12-0.25<0.12<0.12<0.12<0.12244
Example 104a0.50.12-80.120.12-160.12>64>0.5>0.5
Example 104b0.50.120.120.120.120.50.50.5
Example 105<0.06-0.25<0.06<0.06<0.06<0.06-0.120.5-21-21-2
Example 106<0.03<0.03<0.03<0.03<0.030.5-21-21-2
Example 106a0.25<0.06<0.060.120.25448
Example 106b0.5<0.120.50.50.581616
Example 1070.25<0.120.254
Example 108<0.5<0.5<0.52
Example 109<0.5<0.5<0.52
Example 110<0.5<0.5<0.52
Example 11110.50.51
Example 112<0.12<0.12<0.120.51-222
Example 1130.12<0.06<0.06<0.06<0.06442
Example 1140.5<0.060.250.120.5448
Example 1150.25<0.060.12<0.060.25222
Example 1160.25<0.06<0.06<0.060.25222
Example 1170.25<0.060.12<0.060.25244
Example 118<0.06<0.06<0.06<0.06<0.06<0.5-21-21-2
Example 119<0.5<0.51<0.5<0.522>64
Example 120<0.5<0.5<0.5<0.5<0.5111
Example 1210.25<0.06<0.06<0.060.25242
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 96a>128>128>128>128128>12832>128
Example 96b88888814
Example 97>64>64
Example 97a168
Example 97b44
Example 98b12864
Example 98c1616
Example 99b321632161616416
Example 99c44444424
Example 100b88
Example 100c44
Example 101643264323232232
Example 101a161616161616216
Example 1022-42-42-42-42-42-42-41-22-4
Example 103888444428
Example 10444422-422-422-4
Example 104a>0.5>0.5>0.5>64>64>64>640.5>64
Example 104b0.50.50.50.50.50.50.50.50.5
Example 1051-21-21-21-21-21-20.5-21-21-2
Example 1061-21-21-21-20.5-20.5-20.5-20.5-21-2
Example 106a448484824
Example 106b8816888844
Example 10748448428
Example 10822222212
Example 10922221212
Example 11044244224
Example 1112222120.52
Example 11222-42221-220.5-22
Example 113222222222
Example 114484444428
Example 115242222222
Example 116222222222
Example 117442222224
Example 1181-21-21-21-21-21<0.5-1<0.5-21-2
Example 119242224214
Example 120111111111
Example 121242222224
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 1220.12<0.060.12<0.06<0.06222
Example 12321210.581616
Example 1241<0.06<0.06<0.060.12444
Example 12510.120.250.250.5323232
Example 1261<0.06<0.06<0.060.12888
Example 127<0.12<0.12<0.12<0.120.25442
Example 1280.25<0.060.120.250.5444
Example 129<0.06<0.06<0.06<0.06<0.06222
Example 130814816323264
Example 1320.50.120.250.250.58816
Example 133<0.5<0.54<0.5<0.5488
Example 1350.25<0.06<0.06<0.060.25222
Example 1368142864>64>64
Example 1370.5<0.060.250.120.254-84-84-8
Example 137a16416816>64>64>64
Example 137b41224323264
Example 1380.12<0.06<0.06<0.060.25484
Example 140<0.5<0.5<0.5<0.5<0.5<111
Example 141>64>64>64>64>64>64>64>64
Example 1430.5-1<0.06-0.120.25-0.50.12-0.50.25-14-1688-16
Example 144<0.06<0.06<0.06<0.06<0.06224
Example 145<0.5<0.5<0.5<0.51<0.511
Example 1460.12<0.06<0.06<0.06<0.068816
Example 147<0.12<0.5-<0.5>0.12<0.50.5-10.50.5
Example 1491<0.52<0.5<0.5888
Example 15010.120.250.250.5448
Example 150a32816816>64>64>64
Example 15140.5112163232
Example 15280.5224323232
Example 1530.5<0.06<0.06<0.060.25488
Example 154<0.06<0.06<0.06<0.06<0.06222
Example 155<0.120.12<0.5-<0.50.12>0.12<0.50.5-10.50.5
Example 1560.5<0.060.120.120.25488
Example 15716444864>64>64
Example 1580.25<0.06<0.060.120.25444
Example 16110.120.50.51161616
Example 1620.12<0.06<0.060.120.12161632
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 122242222242
Example 123816168888816
Example 124444444410.25
Example 125323232323232321632
Example 126888888888
Example 127444224442
Example 128444444444
Example 129222222222
Example 1303283232328643216
Example 13281688888416
Example 133888488828
Example 135222222222
Example 136>64>64>6464>64>6464864
Example 1374-84-84-844-84-84-82-44-8
Example 137a>64>64>64>64>64>64>641664
Example 137b32326432326432832
Example 138488444824
Example 1401111<0.51111
Example 141>64>64>64>64>64>64>6464>64
Example 1438-168-168-164-168-168-168-162-88-16
Example 144244222224
Example 145121111111
Example 1468816888888
Example 1470.5-10.5-10.5-10.50.5-21-221-20.5-2
Example 149888888828
Example 150888888848
Example 150a>64>64>64>64>64>64>641664
Example 15132323264323232832
Example 152326432323232321632
Example 153888484428
Example 154222222221
Example 155<0.5-<0.5<0.5-<0.50.5-10.50.5-1<0.5-11-21-20.5-1
Example 156888884828
Example 157>64>64>64>64>6464>64864
Example 158844444824
Example 16116161616161616816
Example 16216323216161632164
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 163<0.5<0.51<0.5<0.5448
Example 1640.12<0.06<0.06<0.060.12488
Example 164a10.25110.5161616
Example 1651<0.060.120.120.12161616
Example 1661132
Example 16720.25111323232
Example 168<0.12<0.12<0.12<0.120.5222
Example 1693288816>64>64>64
Example 170<0.06<0.06<0.06<0.06<0.06444
Example 172<0.06<0.06<0.06<0.060.12448
Example 173<0.12<0.12<0.12<0.12<0.12222
Example 174<0.06<0.06<0.06<0.06<0.06222
Example 1750.12<0.06<0.06<0.06<0.06444
Example 177<0.06<0.06<0.06<0.06<0.06222
Example 178<0.06<0.06<0.06<0.060.122116
Example 17910.120.120.250.25323232
Example 180<0.06<0.06<0.06<0.06<0.06422
Example 181<0.06<0.06<0.06<0.060.5244
Example 1823288464>64>64>64
Example 183<0.06<0.06<0.06<0.06<0.06824
Example 1840.12<0.06<0.06<0.060.25323232
Example 1851<0.06<0.060.1216>64>64>64
Example 186<0.06<0.06<0.06<0.060.25222
Example 187<0.12<0.12<0.12<0.120.56416128
Example 1901648816323232
Example 19120.25212888
Example 1920.5<0.060.50.250.5244
Example 193<0.06<0.06<0.060.12<0.06121
Example 194<0.060.12<0.060.25<0.06121
Example 1950.50.120.120.120.120.50.50.5
Example 196>6464646432>64>64>64
Example 1971688416>64>64>64
Example 198<0.12<0.12<0.12<0.12<0.12111
Example 199<0.12<0.12<0.12<0.12<0.12244
Example 2000.12<0.06<0.06<0.06<0.060.542
Example 201<0.12<0.12<0.12<0.12<0.12111
Example 2022<0.58<0.51161664
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 163848488484
Example 1648816488848
Example 164a161616161681648
Example 165161632161616161616
Example 1663232323232
Example 16732323232323232832
Example 168222222212
Example 169>64>64>64>64>64>64>6432>64
Example 170442444444
Example 172844288884
Example 173222112121
Example 174111221122
Example 175448444442
Example 177422142221
Example 1784220.544484
Example 179323232163232321616
Example 180222242222
Example 181212222444
Example 182>64>64>64>64>64>64>64>64>64
Example 183844282842
Example 184321632323216323232
Example 185>6432>64>64>6432>64>6464
Example 186222122222
Example 1876432641664161281616
Example 19032323232323232816
Example 191168168168844
Example 192442242422
Example 1931220.511122
Example 1941210.521122
Example 1950.50.50.50.50.50.50.50.50.5
Example 196>6464>64>64>6464>64832
Example 197>6464>6464>6464>64816
Example 198111111111
Example 199444244422
Example 200244244424
Example 20111111110.51
Example 20232323216323216432
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 20310.120.250.50.5488
Example 20410.250.50.50.5161616
Example 205<0.12<0.12<0.12<0.12<0.12442
Example 2060.25<0.12<0.12<0.121221
Example 207<0.12<0.12<0.12<0.12<0.12422
Example 2080.12<0.06<0.06<0.060.12888
Example 209<0.06<0.064
Example 2100.25<0.06<0.060.25216832
Example 210a2<0.060.250.51888
Example 2121<0.060.250.51888
Example 214<0.12<0.12<0.12<0.12<0.12222
Example 215<0.12<0.12<0.12<0.12<0.12111
Example 2160.5<0.060.250.250.5444
Example 21720.250.511161632
Example 2180.25<0.060.120.120.5444
Example 2192120.528816
Example 220<0.06<0.06<0.06<0.06<0.06122
Example 221<0.12<0.12<0.12<0.12<0.12221
Example 222>6432646464>64>64>64
Example 223>6432>646464>64>64>64
Example 224<0.12<0.120.250.250.25444
Example 2250.5<0.1210.50.581616
Example 22640.5442163232
Example 22764326432326464128
Example 228168888323232
Example 229>128>128>128>128>128>128>128>128
Example 229a>128>128>128>128>128>128>128>128
Example 229b>128128128128>128128>128>128
Example 2300.5<0.060.120.120.25848
Example 230a<0.06-0.12<0.06<0.06<0.06<0.06-0.252-42-42-4
Example 230b0.5<0.120.250.250.5888
Example 230c3216323264>128>128>128
Example 231<0.06<0.06<0.06<0.06<0.0642-42-4
Example 231a<0.06<0.06<0.06<0.06<0.062-421-2
Example 231b1-8<0.06-20.5-80.25-21-88-6416-6416-128
Example 231c<0.12<0.12<0.12<0.12<0.12484
Example 23220.510.52163232
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 203888888448
Example 20416161616161616816
Example 205424222244
Example 206222112122
Example 207444244421
Example 208888888884
Example 20914144
Example 210321632163232323216
Example 210a888884844
Example 212888888844
Example 214222221222
Example 21510.5110.50.510.50.5
Example 216444444444
Example 21716323216161616816
Example 218444444444
Example 2198888168844
Example 220212121112
Example 221222122212
Example 222>64>64>64>64>64>64>646464
Example 223>6464>64>64>64>64>646464
Example 22442444240.52
Example 22584161684814
Example 2263216323232163228
Example 2276481286464326488
Example 22832163232321632168
Example 229>128>128>128>128>128>128>128>128128
Example 229a>128>128>128>128>128>128>128>128128
Example 229b>128128>128>128>128>128>12812864
Example 230888488828
Example 230a2-42-42-41-42-42-42-41-22-4
Example 230b88848880.52
Example 230c>128128>128>128>128128>12832128
Example 2314442-44441-22-4
Example 231a4441-2222-422
Example 231b8-1288-12816-1288-648-1288-12816-1284-168-64
Example 231c444444444
Example 23232323264321632432
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 2340.50.120.250.250.5488
Example 2350.25-0.5<0.06<0.06-0.120.120.25444-8
Example 2360.12<0.06<0.06<0.06<0.06422
Example 23720.250.50.51161632
Example 23820.5111161632
Example 2390.25<0.06<0.06<0.060.25444
Example 239a1<0.060.250.252888
Example 2400.5<0.120.25<0.120.51688
Example 241<0.06<0.06<0.06<0.06<0.06442
Example 241a<0.06<0.06<0.06<0.06<0.06422
Example 24220.50.512161616
Example 24332816323264>64>64
Example 243a1612168323232
Example 24440.5112323264
Example 24541424163216
Example 245a1<0.1210.51484
Example 245b81848326464
Example 245c128326464128>128>128>128
Example 24620.5224163232
Example 246a0.5<0.120.250.250.5484
Example 246b6432643264128128128
Example 246c>12864128128>128>128>128>128
Example 248646412864326432128
Example 24912832646412832128128
Example 251>646464>64
Example 251a32816>64
Example 251b41232
Example 253328161632>64>64>64
Example 253a10.250.50.51161632
Example 253b1<0.060.250.2518816
Example 25441688
Example 254b<0.5<0.5<0.58
Example 255321616>0.5>0.5>0.5
Example 255a643232>0.5>0.5>0.5
Example 256>64>6464>64
Example 256a>646464>64
Example 25720.2510.250.120.50.50.5
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 234888888828
Example 235444-844440.5-24
Example 236444244422
Example 23716163216161616416
Example 23832323216161632416
Example 239444444424
Example 239a8816888848
Example 240161616816161624
Example 241444244424
Example 241a444242222
Example 24216161616161616816
Example 243>6464>6464>6464>643232
Example 243a323232323232321616
Example 24432326432323232432
Example 24516163232321616416
Example 245a848884424
Example 245b64326432643264832
Example 245c>128>128>128>128>128>128>12864>128
Example 246168321616161648
Example 246a424444422
Example 246b128128>1281281281281283264
Example 246c>128128>128>128>128>128>12812864
Example 248128166432643232168
Example 2496464128641664326432
Example 251>64>64>64>64>64>6464>64
Example 251a>64>64>64>64>64>6416>64
Example 251b646464646464464
Example 253>64>64>64>64>64>64>643264
Example 253a32163216161616416
Example 253b888888848
Example 25484884824
Example 254b84484884
Example 255>0.5>0.5>0.5>0.5>0.5>64>6416>0.5
Example 255a>0.5>0.5>0.5>0.5>0.5>64>6432>0.5
Example 256>64>64>64>64>64>6464>64
Example 256a>64>64>64>64>64>6432>64
Example 257>0.50.5>0.50.50.5161620.5
StreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaeStreptococcuspneumoniaeStreptococcusStreptococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)pneumoniae (GC 4565)(ATCC 6301)pyogenes (GC 4563)pyogenes (ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)
Example 257a81410.12>0.50.5>0.5
Example 257b10.250.50.250.120.50.50.5
Example 261a>64>64>64
Example 261b8464
Example 261c4432
Example 262a3232>128
Example 262b1116
Example 2633232>64
Example 264a8464
Example 264b4432
Example 265a4464
Example 265b8464
Example 270a1116
Example 270b2216
Example 271a4216
Example 277a>128>128>128>128>128>128>128>128
Example 277b>64>64>6464>64>64>64>64
Example 278b41212323264
Example 278c20.5111163232
Example 279a>6464>646464>64>64>64
Example 280a>128128>128>128>128>128>128>128
Example 280b128641283264>128>128>128
Example 282>128128>128128>128>128>128>128
Example 283a6416161664128>128>128
Example 283b6416323264128>128>128
Example 283c1648816128128>128
Example 284b>128128>128>128>128>128>128>128
Example 287>64646464>64>64>64>64
Example 296>128128>128>128>128>128>128>128
EXAMPLEEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
NUMBERfaecalis (GC 4552)faecalis (GC 4553)faecalis (GC 4554)faecalis (GC 6189)faecalis (ATCC 29212)faecium (GC 2243)faecium (GC 4556)faecium (GC 4557)avium (GC 4558)
Example 257a>0.5>0.5>0.5>0.5>0.5>32>328>0.5
Example 257b>0.50.5>0.50.50.5161620.5
Example 261a>64>64>64>64>64>64>64>64
Example 261b6464>64>64>64641664
Example 261c646464646464864
Example 262a>128>128>128>128>128>128>128>128
Example 262b323232321616216
Example 263>64>64>64>64>64>6432>64
Example 264a>64>64>6464>646432>64
Example 264b646464646464864
Example 265a>64>64>6464>6464864
Example 265b6464>64646464864
Example 270a161632161616416
Example 270b323232323232832
Example 271a323232323264432
Example 277a>128>128>128>128>128>128>128128128
Example 277b>64>64>64>64>64>64>64>64>64
Example 278b32323232323232832
Example 278c32323232323232832
Example 279a>64>64>64>64>64>64>6464>64
Example 280a>128>128>128>128>128>128>128>128>128
Example 280b>128>128>128>128>128128>12864128
Example 282>128>128>128>128>128>128>128128128
Example 283a>128>128>128>128>128>128>12864128
Example 283b>128>128>128>128>128>128>12864128
Example 283c128128>12812812812812816128
Example 284b>128>128>128>128>128>128>128128128
Example 287>64>64>64>64>64>64>646464
Example 296>128>128>128>128>128>128>128128128
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 3>128>128>128>128>128>128
Example 6>128>128>128>128>128>128
Example 8>128>128>128>128>128>128
Example 10>64>64>64>64>64>64>64>64
Example 12>128>128>128>128>128>128>128>128
Example 136464646464646464
Example 14>128>128>128>128>128>128>128>128
Example 15>128>128>128>128>128>128>128>128
Example 161281281286412812832128
Example 17>64>64>64>64>64>64>64>64
Example 18>128>128>128>128>128>128>128>128
Example 19>128>128>128>128>128>128>128>128
Example 22>128>128>128>128>128>128>128>128
Example 24>64>64>64>64>64>64>64>64
Example 25>128>128>128>128>128>128>128>128
Example 261616163216163232
Example 2716168168888
Example 2884488848
Example 2988888888
Example 3081616168888
Example 31161616168161616
Example 3222422224
Example 33416888488
Example 343216323232163232
Example 3588888888
Example 36>128>128>128>128>128>128>128>128
Example 378888881616
Example 383264646464643264
Example 39161681616161616
Example 406464646464323264
Example 41>64>64>64>64>64>64>64>64
Example 4228422224
Example 446464326464161664
Example 45888168888
Example 4688888888
Example 473232161616161616
Example 481616161616161632
Example 4944444428
Example 513232643232323232
Example 5216163216816816
Example 5342442422
Example 53a>128>128>128>128>128>128>128>128
Example 54>128>128>128>128>128>128>128>128
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 3>128>128>128>128128>128128
Example 6>128>128>128>128>128>128>128
Example 8>128>128>128>128>128>128>128
Example 10>64>64>64>64>64>64>64
Example 12>128>128>128>128>128>128>128
Example 1364646464326432
Example 14>128>128>128>128>128>128>128
Example 15>128>128>128>128>128>128>128
Example 1664816324328
Example 17>64>6464>6432>6464
Example 18>12812812812864>128128
Example 19>128>128>128>128128>128>128
Example 22>128>128>12812864>128128
Example 24>64646464>64>6432
Example 25>128>128>128>128>128>128>128
Example 261648164164
Example 278488884
Example 284484442
Example 298444284
Example 3084841684
Example 311688816164
Example 322221242
Example 334444184
Example 3416816164328
Example 358888882
Example 36>128646412864>12864
Example 3788168884
Example 3864163232646416
Example 3916888484
Example 4064161632163216
Example 41>646464>643264
Example 422221141
Example 4432646482168
Example 458448484
Example 46484824
Example 47881620.58
Example 4816848416
Example 49214214
Example 5132321616464
Example 521648848
Example 53212212
Example 53a>128>128>128>128>128>128
Example 54>128>128>128>128>128>128
StreptococcusStreptococcusStreptococcusStreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaepneumoniaepneumoniaepyogenespyogenesEnterococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)(GC 4565)(ATCC 6301)(GC 4563)(ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)faecalis (GC 4552)
Example 3>128>128>128>128>128
Example 6>128>128>128>128>128
Example 8>128>128>128>128>128
Example 10>64>64>64>64>64>64>64>64>64
Example 12128128128>128>128>128>128>128>128
Example 1316244864>64>64>64
Example 1412812864>128>128>128>128>128>128
Example 1512812864>128>128>128>128>128>128
Example 16646412812816>128>128>128>128
Example 17>6464>64>64>64>64>64>64>64
Example 1812864128128128>128>128>128>128
Example 19>12864128128>128>128>128>128>128
Example 223288832>128>128>128>128
Example 24>6464>64>646464>64>64>64
Example 25>128128>128>128>128>128>128>128>128
Example 2616163232864326464
Example 2732321616832323264
Example 28444414888
Example 29323232321632326464
Example 30816168432326464
Example 313232641686464128128
Example 321616161684888
Example 33323264321616163216
Example 3432163232832323232
Example 3588168216163232
Example 36>128128>128>128128>128>128>128>128
Example 3716161632416161616
Example 383232643232128128>128128
Example 39168168416161616
Example 4064321286432128128>128>128
Example 416464>6464326464>6464
Example 42816168488168
Example 441616328416163216
Example 4516163216416323216
Example 4688881816328
Example 47228414323216
Example 481683216864646464
Example 49488821616322
Example 5116488864>64>64>64
Example 5288168832323232
Example 53114118888
Example 53a6432646464>128>128>128>128
Example 54>128128>128>128>128>128>128>128>128
EnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
EXAMPLEfaecalisfaecalisfaecalisfaecalisfaeciumfaeciumfaeciumaviumEscherichiaEscherichiaEscherichia
NUMBER(GC 4553)(GC 4554)(GC 6189)(ATCC 29212)(GC 2243)(GC 4556)(GC 4557)(GC 4558)coli (GC 4559)coli (GC 4560)coli (ATCC 25922)
Example 3>128>128>128>128>128>128>128>12864>128
Example 6>128>128>128>128>128>128>128>128>128>128
Example 8>128>128>128>128>128>128>128>128>128>128
Example 10>64>64>64>64>64>64>64>64>64>64>64
Example 12>128>128>128>128>128>128>128128>128128>128
Example 1364>64>64>6464646464>6432>64
Example 14>128>128>128>128>128>128>128128>128128>128
Example 15>128>128>128>128>128>128>128128>128128>128
Example 1664>128>128>128128>1281612832832
Example 17>64>64>64>64>64646464321664
Example 18128>128>128>128>128>12864128321664
Example 19128>128>128>128>128>128128128128128128
Example 22>128>128>128>128>128>12864>128>128>128>128
Example 2432>64>646464643264>6432>64
Example 25>128>128>128>128>128>128128128>128>128>128
Example 26326432323264832641664
Example 2716323232326481632832
Example 284888884464864
Example 2916323232166481616416
Example 3016643264326481632832
Example 3116128646432448>12832>128
Example 328448482416416
Example 331616163286448641664
Example 34323264643264816641664
Example 35832161683248>12816>128
Example 36128>128>128>128>128>12812812812864>128
Example 37416161681648>1284128
Example 38641281281281281283264643264
Example 3983216168328812816128
Example 4064>128128128641281664321632
Example 416464>646464326464>64>64>64
Example 4288884162432132
Example 44832161683284>6464>64
Example 451616163216324816416
Example 4641616841684641664
Example 474643284842>6432>64
Example 481664646416644832432
Example 49416161688248416
Example 51>64>64>64>64>64>641664648>64
Example 52166432641632832641664
Example 534164828241284128
Example 53a>128>128>128>128>128>128>128>128>128>128>128
Example 54>128>128>128>128>128>128128128>128>128>128
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 54a>128>128>128>128>128>128>128>128
Example 5881632161616816
Example 59>128>128>128>128>128>128>128>128
Example 60>128>128>128>128>128>128>128>128
Example 60a>128>128>128>128>128>128>128>128
Example 61>128>128128>128>128>128>128>128
Example 62>128>128>128>128>128>128>128>128
Example 64>128>128>128>128>128>128>128>128
Example 65>128>128>128>128>128>128>128>128
Example 66168888848
Example 66a>128>128>128>128>128>128>128>128
Example 67>128>128>128>128>128>128>128>128
Example 69>128>128>128>128>128>128>128>128
Example 71>128>128>128>128>128>128>128>128
Example 72>128>128>128>128>128>128>128>128
Example 73>128>128>128>128>128>128>128>128
Example 74>128>128>128>128>128>128>128>128
Example 764-82-82-82-42-84-82-82-8
Example 77168-16164-88-161688-16
Example 7888848888
Example 7984444844
Example 803232643232323232
Example 81>128>128>128>128>128>128>128>128
Example 82168168161688
Example 8344424422
Example 8488848888
Example 896464646464646464
Example 92>128>128>128>128>128>128>128>128
Example 93>128>128>128>128>128>128>128>128
Example 94>64>64>64>64>64>64>64>64
Example 95>64>64>64>64
Example 95a4844
Example 95b1211
Example 96c0.50.5110.51
Example 96>128>128>128>128>128>128
Example 96a>128128>128>128>128>128
Example 96b212211
Example 97>64>64>64>64
Example 97a2210.5
Example 97b1110.5
Example 98b1616168
Example 98c2422
Example 99b444444
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 54a>128128128>128>128>128
Example 58444448
Example 59>128>128>128>128>128>128>128
Example 60>128>128>128>128>128>128>128
Example 60a>128>128>128>128>128>128>128
Example 61>128>128128>128128>128>128
Example 62>128>128>128>128>128>128>128
Example 64>128>128>128>128>128>128>128
Example 65>128>128>128>128>128>128
Example 668448484
Example 66a>128>128>128>128>128>128
Example 67>128>128128>128>128>128>128
Example 69>128>128>128>128>128>128>128
Example 71>128>128>128>128>128>128>128
Example 72>128>128>128>128>128>128>128
Example 73>128>128>128>128>128>128>128
Example 74>128>128>128>128>128>128>128
Example 761-42-42-42-42-42-80.5-2
Example 7784-8444-882
Example 784444882
Example 794444244
Example 803232323232328
Example 81>128>128>128>128>128>128>128
Example 82844448
Example 83222122
Example 844444442
Example 8964323264646432
Example 92>128>128>128>128>128>128
Example 93>128>128>128>128>128>128
Example 94>64>64>64>64>64>64
Example 95>64>64>64
Example 95a844
Example 95b211
Example 96c0.50.510.25110.5
Example 96>128>128>128>128>128>128128
Example 96a>128128128>1286412864
Example 96b2110.50.520.5
Example 97>64>64>64
Example 97a422
Example 97b111
Example 98b1688
Example 98c211
Example 99b4444282
StreptococcusStreptococcusStreptococcusStreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaepneumoniaepneumoniaepyogenespyogenesEnterococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)(GC 4565)(ATCC 6301)(GC 4563)(ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)faecalis (GC 4552)
Example 54a>128128>128>128>128>128>128>128>128
Example 58168168864646464
Example 59>12864128128>128>128>128>128>128
Example 60>12864128128>128>128>128>128>128
Example 60a>12864128>128>128>128>128>128>128
Example 611286464128128128128128128
Example 62>12864128128>128>128>128>128>128
Example 64128128>128>128>128>128>128>128>128
Example 65>128128128128128>128>128>128>128
Example 66323264321616323232
Example 66a>128>128>128>128>128>128>128>128>128
Example 6712864128128128128128128128
Example 69128128128128>128>128>128>128>128
Example 7l>128>128>128>128>128>128>128>128>128
Example 7212816646464>128>128>128>128
Example 73>12864128128>128>128>128>128>128
Example 74128128>128>128>128>128>128>128>128
Example 760.25-2<0.06-0.250.25-4<0.12-10.25-24-164-164-324-16
Example 7710.25-0.52-42116161616
Example 7810.25210.51616168
Example 79488441683232
Example 8084168832646464
Example 81128128>128>128>128>128>128>128>128
Example 820.50.2522116161616
Example 830.25<0.120.250.50.254444
Example 8410.12110.58888
Example 893248163264646464
Example 92>128128128128>128>128>128>128>128
Example 93>128128>128>128>128>128>128>128>128
Example 94>64>64>64>64>64>64>64>64>64
Example 95>64>64
Example 95a1632
Example 95b88
Example 96c<0.06<0.06<0.0612
Example 96>128>128>128>128>128
Example 96a321632>128>128
Example 96b0.25<0.120.2548
Example 97>64>64
Example 97a416
Example 97b24
Example 98b64128
Example 98c816
Example 99b2<0.511632
EnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
EXAMPLEfaecalisfaecalisfaecalisfaecalisfaeciumfaeciumfaeciumaviumEscherichiaEscherichiaEscherichia
NUMBER(GC 4553)(GC 4554)(GC 6189)(ATCC 29212)(GC 2243)(GC 4556)(GC 4557)(GC 4558)coli (GC 4559)coli (GC 4560)coli (ATCC 25922)
Example 54a>128>128>128>128>128>128128128>128>128>128
Example 5832646464326483281616
Example 59>128>128>128>128>128>128128128>128>128>128
Example 60128>128>128>128>128>128128128>12816>128
Example 60a128>128>128>128>128>128128128>12816>128
Example 61128128128128>128128128641288128
Example 62128>128>128>128>128>12864128>1284>128
Example 64>128>128>128>128>128>128>128128>128>128>128
Example 65128>128>128>128128>128128128>12832>128
Example 66864321683244>1284>128
Example 66a>128>128>128>128>128>128>128128>1288>128
Example 67128>128128128>128>12812864>12832>128
Example 69>128>128>128>128>128>128128128>128>128>128
Example 71>128>128>128>128>128>128>128>128>128128>128
Example 7264>128>128>128>128>12812864>12832>128
Example 73>128>128>128>128>128>128128128>12816>128
Example 74>128>128>128>128>128>128128128>128>128>128
Example 764-84-324-164-162-84-161-22-864->642-464->64
Example 77816-3216168161-24>1284>128
Example 78816168816241284128
Example 794168883242>1282>128
Example 803264646432641632>648>64
Example 81128>128>128>128>128>128128128>128128>128
Example 82832161681624>1284>128
Example 832444241232264
Example 84816884818644>64
Example 896464646464643232>6432>64
Example 92128>128>128>128>128>128128128>128>128>128
Example 93>128>128>128>128>128>128128128>128>128>128
Example 94>64>64>64>64>64>64>64>64>6464>64
Example 95>64>648
Example 95a32>642
Example 95b464<0.5
Example 96c222221264
Example 96>128>128>128>128>128128>128>128
Example 96a>128>128>128128>12832>128>128
Example 96b8888814>128
Example 97>64>642
Example 97a8>641
Example 97b4321
Example 98b64>1282
Example 98c16640.5
Example 99b1632161616416>64
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 99c221211
Example 100b2222
Example 100c1111
Example 101448844
Example 101a424442
Example 102211-21-20.5-11-20.5-11-2
Example 10321222212
Example 10421110.510.5-11
Example 104a0.5-640.50.50.5-320.50.50.50.5-64
Example 104b0.50.50.50.50.50.50.50.5
Example 1050.25-10.5-11-2<0.5-10.5-10.25-2<0.5-1<0.5-1
Example 1060.5-20.5-20.5-20.5-20.25-10.25-20.5-20.5-2
Example 106a22222422
Example 106b8881681688
Example 107221211
Example 108111111
Example 109111111
Example 110111211
Example 111111111
Example 1120.5-1110.5-21-21
Example 11321111211
Example 11422221222
Example 11511110.510.51
Example 11611110.5111
Example 11721211211
Example 118<0.5-1<0.5-11<0.5-1<0.5-1<0.5-1<0.5-1<0.5-1
Example 11911211111
Example 120<0.5<0.51<0.5<0.5<0.5<0.5<0.5
Example 12121111221
Example 12222222122
Example 12388844888
Example 12422221222
Example 125323232832323232
Example 12688888888
Example 12742242422
Example 12842222422
Example 12922222224
Example 1303232323232323232
Example 13222422424
Example 13321412211
Example 13511111211
Example 136161632816161616
Example 13721-22-41-21-222-41-2
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 99c1111121
Example 100b211
Example 100c111
Example 1014422181
Example 101a8111121
Example 1020.5-10.5-110.5-10.5-11-20.5
Example 1031121121
Example 1040.5-10.510.5-10.510.5
Example 104a0.5-64323216-3216-323216
Example 104b0.50.544482
Example 1050.25-1<0.5-10.5-1<0.5-10.5-1<0.5-10.5-1
Example 1060.25-10.5-10.5-20.25-1<0.12-10.25-10.25
Example 106a222112
Example 106b848448
Example 1071111111
Example 108111<0.5111
Example 109111<0.5111
Example 1101111111
Example 111110.510.511
Example 1120.5-110.5-10.5-10.5-10.5-110.5
Example 1131110.5110.5
Example 1142121221
Example 11510.510.5110.5
Example 11610.511110.5
Example 1171111120.5
Example 118<0.5-1<0.5-<0.5<0.5-10.25-0.25<0.5-<0.5<0.5-10.25-0.25
Example 119111111<0.5
Example 120<0.5<0.51<0.5<0.5<0.5<0.5
Example 1211110.50.521
Example 1222221121
Example 1234884484
Example 1242221121
Example 12532323232323232
Example 1268888888
Example 127224212
Example 1282242242
Example 1292221141
Example 13032323232163232
Example 1322121121
Example 133111<0.5111
Example 13510.510.50.510.5
Example 1361616884324
Example 1371-211-20.5-20.5-11-21
StreptococcusStreptococcusStreptococcusStreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaepneumoniaepneumoniaepyogenespyogenesEnterococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)(GC 4565)(ATCC 6301)(GC 4563)(ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)faecalis (GC 4552)
Example 99c<0.5<0.5<0.544
Example 100b88
Example 100c24
Example 1012<0.521664
Example 101a1<0.51816
Example 102<0.12-0.25<0.06<0.12-<0.1<0.06<0.12-0.252-42-42-42-4
Example 1030.50.120.120.120.254888
Example 104<0.12-0.25<0.12<0.12<0.12<0.122444
Example 104a0.50.12-80.120.12-160.12>64>0.5>0.5>0.5
Example 104b0.50.120.120.120.120.50.50.50.5
Example 105<0.06-0.25<0.06<0.06<0.06<0.06-0.120.5-21-21-21-2
Example 106<0.03<0.03<0.03<0.03<0.030.5-21-21-21-2
Example 106a0.25<0.06<0.060.120.254484
Example 106b0.5<0.120.50.50.5816168
Example 1070.25<0.120.2544
Example 108<0.5<0.5<0.522
Example 109<0.5<0.5<0.522
Example 110<0.5<0.5<0.524
Example 11110.50.512
Example 112<0.12<0.12<0.120.51-2222
Example 1130.12<0.06<0.06<0.06<0.064422
Example 1140.5<0.060.250.120.54484
Example 1150.25<0.060.12<0.060.252222
Example 1160.25<0.06<0.06<0.060.252222
Example 1170.25<0.060.12<0.060.252444
Example 118<0.06<0.06<0.06<0.06<0.06<0.5-21-21-21-2
Example 119<0.5<0.51<0.5<0.522>642
Example 120<0.5<0.5<0.5<0.5<0.51111
Example 1210.25<0.06<0.06<0.060.252422
Example 1220.12<0.060.12<0.06<0.062222
Example 12321210.5816168
Example 1241<0.06<0.06<0.060.124444
Example 12510.120.250.250.532323232
Example 1261<0.06<0.06<0.060.128888
Example 127<0.12<0.12<0.12<0.120.254424
Example 1280.25<0.060.120.250.54444
Example 129<0.06<0.06<0.06<0.06<0.062222
Example 13081481632326432
Example 1320.50.120.250.250.588168
Example 133<0.5<0.54<0.5<0.54888
Example 1350.25<0.06<0.06<0.060.252222
Example 1368142864>64>64>64
Example 1370.5<0.060.250.120.254-84-84-84-8
EnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
EXAMPLEfaecalisfaecalisfaecalisfaecalisfaeciumfaeciumfaeciumaviumEscherichiaEscherichiaEscherichia
NUMBER(GC 4553)(GC 4554)(GC 6189)(ATCC 29212)(GC 2243)(GC 4556)(GC 4557)(GC 4558)coli (GC 4559)coli (GC 4560)coli (ATCC 25922)
Example 99c444442464
Example 100b8>1280.5
Example 100c4320.5
Example 1013264323232232>64
Example 101a161616161621664
Example 1022-42-42-42-42-42-41-22-416-320.5-116-64
Example 1038844442864164
Example 1044422-422-422-416-320.5-132-64
Example 104a>0.5>0.5>64>64>64>640.5>64>640.5-16>64
Example 104b0.50.50.50.50.50.50.50.5>0.50.5>0.5
Example 1051-21-21-21-21-20.5-21-21-2320.5-216-32
Example 1061-21-21-20.5-20.5-20.5-20.5-21-232-640.5-232-64
Example 106a4848482432232
Example 106b81688884432864
Example 107844842864
Example 108222221232
Example 109222121216
Example 110424422464
Example 111222120.5232
Example 1122-42221-220.5-22>16132
Example 1132222222232132
Example 1148444442864164
Example 1154222222264132
Example 1162222222264132
Example 1174222222432164
Example 1181-21-21-21-21<0.5-1<0.5-21-216116-32
Example 1194222421432132
Example 1201111111116<0.516
Example 1214222222432132
Example 1224222224232232
Example 12316168888816>648>64
Example 12444444410.2532132
Example 1253232323232321632>6432>64
Example 1268888888864864
Example 1274422444264464
Example 1284444444432432
Example 1292222222232232
Example 13083232328643216>6464>64
Example 1321688888416321>64
Example 1338848882832<0.564
Example 13522222222320.532
Example 136>64>6464>64>6464864>644>64
Example 1374-84-844-84-84-82-44-832-64164
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 137a3232321632323232
Example 137b161616816161616
Example 13822222222
Example 14011<0.5111<0.51
Example 141>64>64>64>64>64>64>64>64
Example 1432-42-44-82-41-42-82-42-4
Example 1441110.50.5412
Example 145<0.511<0.5<0.5111
Example 14688884888
Example 147<0.5-<0.50.50.5<0.5-<0.50.5-10.5-10.5-1<0.5-<0.5
Example 14922422222
Example 15042822222
Example 150a3232321632321632
Example 151881648848
Example 152161632161616816
Example 15322422222
Example 15411211211
Example 155<0.5-<0.50.50.5<0.5-<0.5<0.5-<0.5<0.5-<0.50.5-1<0.5-<0.5
Example 15622422222
Example 1573216321632321632
Example 15821211222
Example 16188844844
Example 1621632161616161616
Example 16348844444
Example 1644168816848
Example 164a888816888
Example 1651632161616161616
Example 166888
Example 167161616816161616
Example 16811111211
Example 1693232>643232323232
Example 17044124244
Example 17284442844
Example 17320.510.50.5221
Example 17412222112
Example 17544444444
Example 17722222222
Example 178484888416
Example 1793232323232323232
Example 18021222222
Example 18144444444
Example 182>64>64>64>64>64>64>64>64
Example 18382284444
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 137a16161688168
Example 137b8884884
Example 1381241122
Example 14011<0.5<0.5<0.5<0.5<0.5
Example 141>64>64>64>64>64>64>64
Example 1432-40.5-21-21-212-41-2
Example 1441110.250.120.50.25
Example 145<0.5<0.51<0.51<0.50.5
Example 1468884484
Example 1470.5-11-21-2<0.5-1<0.5-1121
Example 1492111111
Example 1502121121
Example 150a16161688328
Example 1518244282
Example 15288888168
Example 1531110.50.520.5
Example 1541120.50.2521
Example 155<0.5-<0.5<0.5-1<0.5-2<0.5-1<0.5-1<0.5-11<0.5
Example 1562221121
Example 15716161688324
Example 15820.521121
Example 1614442282
Example 1621616168888
Example 1631481422
Example 16444410.541
Example 164a8484484
Example 16516161688168
Example 16644444
Example 1671616888168
Example 16810.520.50.51
Example 1693232323216>648
Example 1704841211
Example 1728882242
Example 1730.5120.50.250.50.5
Example 1741220.5110.5
Example 1754482242
Example 1772241241
Example 17848320.5242
Example 17932323232163232
Example 1802221110.5
Example 1814882122
Example 182>64>64>64>64>64>64>64
Example 1834842442
StreptococcusStreptococcusStreptococcusStreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaepneumoniaepneumoniaepyogenespyogenesEnterococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)(GC 4565)(ATCC 6301)(GC 4563)(ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)faecalis (GC 4552)
Example 137a16416816>64>64>64>64
Example 137b4122432326432
Example 1380.12<0.06<0.06<0.060.254844
Example 140<0.5<0.5<0.5<0.5<0.5<1111
Example 141>64>64>64>64>64>64>64>64>64
Example 1430.5-1<0.06-0.120.25-0.50.12-0.50.25-14-1688-168-16
Example 144<0.06<0.06<0.06<0.06<0.062242
Example 145<0.5<0.5<0.5<0.51<0.5111
Example 1460.12<0.06<0.06<0.06<0.0688168
Example 147<0.12<0.5-<0.5>0.12<0.50.5-10.50.50.5-1
Example 1491<0.52<0.5<0.58888
Example 15010.120.250.250.54488
Example 150a32816816>64>64>64>64
Example 15140.511216323232
Example 15280.522432323232
Example 1530.5<0.06<0.06<0.060.254888
Example 154<0.06<0.06<0.06<0.06<0.062222
Example 155<0.120.12<0.5-<0.50.12>0.12<0.50.5-10.50.5<0.5-<0.5
Example 1560.5<0.060.120.120.254888
Example 15716444864>64>64>64
Example 1580.25<0.06<0.060.120.254448
Example 16110.120.50.5116161616
Example 1620.12<0.06<0.060.120.1216163216
Example 163<0.5<0.51<0.5<0.54488
Example 1640.12<0.06<0.06<0.060.124888
Example 164a10.25110.516161616
Example 1651<0.060.120.120.1216161616
Example 1661132
Example 16720.2511132323232
Example 168<0.12<0.12<0.12<0.120.52222
Example 1693288816>64>64>64>64
Example 170<0.06<0.06<0.06<0.06<0.064444
Example 172<0.06<0.06<0.06<0.060.124488
Example 173<0.12<0.12<0.12<0.12<0.122222
Example 174<0.06<0.06<0.06<0.06<0.062221
Example 1750.12<0.06<0.06<0.06<0.064444
Example 177<0.06<0.06<0.06<0.06<0.062224
Example 178<0.06<0.06<0.06<0.060.1221164
Example 17910.120.120.250.2532323232
Example 180<0.06<0.06<0.06<0.06<0.064222
Example 181<0.06<0.06<0.06<0.060.52442
Example 1823288464>64>64>64>64
Example 183<0.06<0.06<0.06<0.06<0.068248
EnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
EXAMPLEfaecalisfaecalisfaecalisfaecalisfaeciumfaeciumfaeciumaviumEscherichiaEscherichiaEscherichia
NUMBER(GC 4553)(GC 4554)(GC 6189)(ATCC 29212)(GC 2243)(GC 4556)(GC 4557)(GC 4558)coli (GC 4559)coli (GC 4560)coli (ATCC 25922)
Example 137a>64>64>64>64>64>641664>648>64
Example 137b326432326432832>644>64
Example 13888444824640.564
Example 140111<0.5111164164
Example 141>64>64>64>64>64>6464>64>64>64>64
Example 1438-168-164-168-168-168-162-88-16641-2>64
Example 144442222243232
Example 1452111111132<0.564
Example 1468168888886464
Example 1470.5-10.5-10.50.5-21-221-20.5-2640.5-264-64
Example 1498888882864<0.5>64
Example 15088888848321>64
Example 150a>64>64>64>64>64>641664>6416>64
Example 151323264323232832>642>64
Example 1526432323232321632>648>64
Example 153884844286464
Example 1542222222132232
Example 155<0.5-<0.50.5-10.50.5-1<0.5-11-21-20.5-1>640.5-2>64
Example 15688884828320.5>64
Example 157>64>64>64>6464>64864>64>64
Example 1584444482464164
Example 161161616161616816>642>64
Example 162323216161632164>6416>64
Example 16348488484648>64
Example 164816488848644>64
Example 164a161616168164832832
Example 1651632161616161616>6416>64
Example 1663232323232>642>64
Example 167323232323232832>1288>128
Example 16822222212160.564
Example 169>64>64>64>64>64>6432>64>648>64
Example 17042444444>644>64
Example 17244288884>642>64
Example 17322112121160.532
Example 17411221122>644>64
Example 1754844444264464
Example 17722142221644>64
Example 178220.544484>6416>64
Example 1793232163232321616>6432>64
Example 18022242222642>64
Example 18112222444>6416>64
Example 182>64>64>64>64>64>64>64>64>64>64>64
Example 18344282842>644>64
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 1843232323232323232
Example 185>64>64>64>64>64>64>64>64
Example 18622221222
Example 1876464326464646464
Example 19016161684161616
Example 19188844844
Example 19241222221
Example 193110.50.50.2510.50.5
Example 1941110.50.5210.5
Example 1950.50.50.50.50.50.50.50.5
Example 196>64>64>6464>64>6464>64
Example 1971664641664323232
Example 19810.50.50.50.250.50.50.5
Example 19921221212
Example 20021211211
Example 2010.250.50.50.50.250.250.250.25
Example 20244844444
Example 20322411211
Example 20484844844
Example 20522222222
Example 20611111111
Example 20722111111
Example 20884484844
Example 209224
Example 2103232323232323232
Example 210a48448844
Example 21242422422
Example 214132221122
Example 2150.50.510.50.50.510.5
Example 21622211212
Example 21744844844
Example 21844444444
Example 21942222824
Example 22011110.510.50.5
Example 22122122221
Example 222>64>64>64>64>64>64>64>64
Example 223>6464>6464646464>64
Example 22442414422
Example 22584848844
Example 226161616816161616
Example 227128128>128128128128128128
Example 2283232323232323232
Example 229>128>128>128>128>128>128>128>128
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 18432323216323216
Example 185>64>64>64>64>64>64>64
Example 1862121120.5
Example 1876412812816643232
Example 19048888168
Example 1914484444
Example 1922121142
Example 1930.50.510.250.250.50.25
Example 1940.50.510.50.510.5
Example 1950.5242142
Example 196>6432326464>6464
Example 19716323288164
Example 1980.50.51<0.120.50.5
Example 1991120.50.51
Example 200112112
Example 2010.50.250.250.250.250.25
Example 2024222442
Example 2032121121
Example 204424424
Example 205222112
Example 20610.510.50.51
Example 2071110.50.54
Example 2084444444
Example 20914112
Example 2103232323283232
Example 210a4844244
Example 2122222221
Example 2140.51110.51
Example 215<0.120.50.50.5<0.120.5
Example 2162121121
Example 217224128
Example 2184444484
Example 2192222241
Example 22010.250.50.250.250.5
Example 221222112
Example 222>64>64>64>64>64>64
Example 223646464646464
Example 224212112
Example 225444224
Example 22688881682
Example 22712864324328
Example 228321616161616
Example 229>128>128>128>128>128>128>128
StreptococcusStreptococcusStreptococcusStreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaepneumoniaepneumoniaepyogenespyogenesEnterococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)(GC 4565)(ATCC 6301)(GC 4563)(ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)faecalis (GC 4552)
Example 1840.12<0.06<0.06<0.060.2532323232
Example 1851<0.06<0.060.1216>64>64>64>64
Example 186<0.06<0.06<0.06<0.060.252222
Example 187<0.12<0.12<0.12<0.120.5641612864
Example 190164881632323232
Example 19120.2521288816
Example 1920.5<0.060.50.250.52444
Example 193<0.06<0.06<0.060.12<0.061211
Example 194<0.060.12<0.060.25<0.061211
Example 1950.50.120.120.120.120.50.50.50.5
Example 196>6464646432>64>64>64>64
Example 1971688416>64>64>64>64
Example 198<0.12<0.12<0.12<0.12<0.121111
Example 199<0.12<0.12<0.12<0.12<0.122444
Example 2000.12<0.06<0.06<0.06<0.060.5422
Example 201<0.12<0.12<0.12<0.12<0.121111
Example 2022<0.58<0.5116166432
Example 20310.120.250.50.54888
Example 20410.250.50.50.516161616
Example 205<0.12<0.12<0.12<0.12<0.124424
Example 2060.25<0.12<0.12<0.1212212
Example 207<0.12<0.12<0.12<0.12<0.124224
Example 2080.12<0.06<0.06<0.060.128888
Example 209<0.06<0.064
Example 2100.25<0.06<0.060.2521683232
Example 210a2<0.060.250.518888
Example 2121<0.060.250.518888
Example 214<0.12<0.12<0.12<0.12<0.122222
Example 215<0.12<0.12<0.12<0.12<0.121111
Example 2160.5<0.060.250.250.54444
Example 21720.250.51116163216
Example 2180.25<0.060.120.120.54444
Example 2192120.5288168
Example 220<0.06<0.06<0.06<0.06<0.061222
Example 221<0.12<0.12<0.12<0.12<0.122212
Example 222>6432646464>64>64>64>64
Example 223>6432>646464>64>64>64>64
Example 224<0.12<0.120.250.250.254444
Example 2250.5<0.1210.50.5816168
Example 22640.544216323232
Example 227432643232646412864
Example 22816888832323232
Example 229>128>128>128>128>128>128>128>128>128
EnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
EXAMPLEfaecalisfaecalisfaecalisfaecalisfaeciumfaeciumfaeciumaviumEscherichiaEscherichiaEscherichia
NUMBER(GC 4553)(GC 4554)(GC 6189)(ATCC 29212)(GC 2243)(GC 4556)(GC 4557)(GC 4558)coli (GC 4559)coli (GC 4560)coli (ATCC 25922)
Example 1841632323216323232>6432>64
Example 18532>64>64>6432>64>6464>64>64>64
Example 1862212222264464
Example 18732641664161281616>128128>128
Example 190323232323232816>6416>64
Example 1918168168844648>64
Example 1924224242232432
Example 193220.511122322
Example 194210.521122322
Example 1950.50.50.50.50.50.50.50.5>0.50.5>0.5
Example 19664>64>64>6464>6483264864
Example 19764>6464>6464>64816641632
Example 1981111111132132
Example 1994424442232164
Example 2004424442432132
Example 2011111110.51160.2516
Example 20232321632321643216232
Example 2038888844832264
Example 2041616161616168161284128
Example 20524222244128164
Example 2062211212232132
Example 2074424442164232
Example 20888888884>64864
Example 20914144>64464
Example 2101632163232323216>6464>64
Example 210a88884844>6416>64
Example 2128888884432232
Example 2142222122264264
Example 2150.5110.50.510.50.532132
Example 2164444444416232
Example 21732321616161681632264
Example 21844444444>64864
Example 21988816884464464
Example 22012121112160.532
Example 2212212221232264
Example 222>64>64>64>64>64>646464>6464>64
Example 22364>64>64>64>64>646464>6432>64
Example 2242444240.52642128
Example 22541616848141284128
Example 226163232321632281284>128
Example 22781286464326488>1288>128
Example 228163232321632168>6416>64
Example 229>128>128>128>128>128>128>128128>128>128>128
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 229a>128>128>128>128>128>128>128>128
Example 229b>128>128>128>128>128>128>128>128
Example 23022212212
Example 230a0.5-21-21-20.5-20.25-21-20.5-11-2
Example 230b42221422
Example 230c12812812864>128128128128
Example 2312-41-21-21-42-42-41-41-4
Example 231a1-211-21-20.5-12-41-21-2
Example 231b4-644-648-644-324-324-644-324-64
Example 231c22222221
Example 23244844444
Example 23422222222
Example 2351-20.5-21-20.5-10.5-21-21-20.5-1
Example 23622224222
Example 23742428424
Example 23844844824
Example 23921242222
Example 239a42444444
Example 24040.5412444
Example 24122222222
Example 241a22222422
Example 24288844848
Example 2436464646464646464
Example 243a3232323232323232
Example 244881681888
Example 24584444844
Example 245a42222222
Example 245b16161681616816
Example 245c>128128>128128128128128128
Example 24684444844
Example 246a41211222
Example 246b128641286464646464
Example 246c>128>128>128>128>128>128>128>128
Example 247>64>64>64>64>64>64>64>64
Example 2483264643264323232
Example 2491281281281286464128128
Example 251>64>64>64>64>64>64
Example 251a>646464>6464>64
Example 251b88816816
Example 252>64>64>64>64>64>64
Example 253>64>64>6464>64>6464>64
Example 253a42444424
Example 253b42824424
Example 254444484
Example 254b448888
Example 255>0.50.50.50.50.50.50.5>0.5
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 229a>128>128>128>128>128>128>128
Example 229b>128>128>128>128>128>128>128
Example 2301110.5120.5
Example 230a0.5-20.25-10.5-20.12-0.50.12-0.50.25-10.25-0.5
Example 230b2121121
Example 230c64646464646432
Example 23121-41-20.5-10.25-0.510.5-1
Example 231a1110.12-0.25>0.12-0.250.50.5
Example 231b4-644-324-322-322-168-321-32
Example 231c1120.50.510.5
Example 2324222142
Example 23421110.521
Example 2350.5-10.25-0.50.5-10.25-0.50.25-0.50.5-10.25-0.5
Example 2362220.50.521
Example 2372121141
Example 2384222241
Example 2392121121
Example 239a2221222
Example 2402242222
Example 2412221242
Example 241a2242141
Example 24284844162
Example 24364646432326432
Example 243a32323232163216
Example 2444442242
Example 2454442182
Example 245a21210.521
Example 245b16888284
Example 245c1281281281286412864
Example 2464444482
Example 246a1111122
Example 246b641286464326464
Example 246c>128>128>128>128>128>128>128
Example 247>64>64>64>64>64>64>64
Example 24832161632323216
Example 2491281286412812864128
Example 251>64>64>64>64>64>6464
Example 251a6464646432>6416
Example 251b88884164
Example 252>64>64>64>64>64>64>64
Example 2536464646464>6432
Example 253a2444181
Example 253b2242242
Example 2544444242
Example 254b4882442
Example 2550.5323264326432
StreptococcusStreptococcusStreptococcusStreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaepneumoniaepneumoniaepyogenespyogenesEnterococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)(GC 4565)(ATCC 6301)(GC 4563)(ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)faecalis (GC 4552)
Example 229a>128>128>128>128>128>128>128>128>128
Example 229b>128128128128>128128>128>128>128
Example 2300.5<0.060.120.120.258488
Example 230a<0.06-0.12<0.06<0.06<0.06<0.06-0.252-42-42-42-4
Example 230b0.5<0.120.250.250.58888
Example 230c3216323264>128>128>128>128
Example 231<0.06<0.06<0.06<0.06<0.0642-42-44
Example 231a<0.06<0.06<0.06<0.06<0.062-421-24
Example 231b1-8<0.06-20.5-80.25-21-88-6416-6416-1288-128
Example 231c<0.12<0.12<0.12<0.12<0.124844
Example 23220.510.5216323232
Example 2340.50.120.250.250.54888
Example 2350.25-0.5<0.06<0.06-0.120.120.25444-84
Example 2360.12<0.06<0.06<0.06<0.064224
Example 23720.250.50.5116163216
Example 23820.511116163232
Example 2390.25<0.06<0.06<0.060.254444
Example 239a1<0.060.250.2528888
Example 2400.5<0.120.25<0.120.5168816
Example 241<0.06<0.06<0.06<0.06<0.064424
Example 241a<0.06<0.06<0.06<0.06<0.064224
Example 24220.50.51216161616
Example 24332816323264>64>64>64
Example 243a161216832323232
Example 24440.511232326432
Example 2454142416321616
Example 245a1<0.1210.514848
Example 245b8184832646464
Example 245c128326464128>128>128>128>128
Example 24620.522416323216
Example 246a0.5<0.120.250.250.54844
Example 246b6432643264128128128128
Example 246c>12864128128>128>128>128>128>128
Example 247>64>64>64>64>64>64>64>64>64
Example 248646412864326432128128
Example 2491283264641283212812864
Example 251>646464>64>64
Example 251a32816>64>64
Example 251b4123264
Example 252>64>64>64>64>64
Example 253328161632>64>64>64>64
Example 253a10.250.50.5116163232
Example 253b1<0.060.250.25188168
Example 254416888
Example 254b<0.5<0.5<0.588
Example 255321616>0.5>0.5>0.5>0.5
EnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
EXAMPLEfaecalisfaecalisfaecalisfaecalisfaeciumfaeciumfaeciumaviumEscherichiaEscherichiaEscherichia
NUMBER(GC 4553)(GC 4554)(GC 6189)(ATCC 29212)(GC 2243)(GC 4556)(GC 4557)(GC 4558)coli (GC 4559)coli (GC 4560)coli (ATCC 25922)
Example 229a>128>128>128>128>128>128>128128>128>128>128
Example 229b128>128>128>128>128>12812864>12832>128
Example 23088488828>64164
Example 230a2-42-41-42-42-42-41-22-4320.25-132
Example 230b8848880.521281128
Example 230c128>128>128>128128>12832128>12832>128
Example 231442-44441-22-4>1280.5-2>128
Example 231a441-2222-422320.5-232-64
Example 231b8-12816-1288-648-1288-12816-1284-168-64>1280.25-4>128
Example 231c44444444>1282>128
Example 232323264321632432642>64
Example 2348888882864164
Example 23544-844440.5-2432->640.5-132->64
Example 23644244422>641>64
Example 23716321616161641664164
Example 238323216161632416>642>64
Example 23944444424>641>64
Example 239a816888848>642>64
Example 2401616816161624>1282128
Example 24144244424>642>64
Exarnple 241a44242222>642>64
Example 242161616161616816>642>64
Example 24364>6464>6464>643232>6464>64
Example 243a3232323232321616>6432>64
Example 244326432323232432642>64
Example 24516323232161641632464
Example 245a4888442432232
Example 245b326432643264832648128
Example 245c>128>128>128>128>128>12864>128>12832>128
Example 2468321616161648644128
Example 246a2444442216216
Example 246b128>1281281281281283264>12832>128
Example 246c128>128>128>128>128>12812864>12832>128
Example 247>64>64>64>64>64>64>64>64>64>64>64
Example 24816643264323216864864
Example 24964128641664326432128128128
Example 251>64>64>64>64>6464>64>644>64
Example 251a>64>64>64>64>6416>64>648>64
Example 251b6464646464464>642>64
Example 252>64>64>64>64>64>64>64>64
Example 253>64>64>64>64>64>643264>642>64
Example 253a163216161616416>642>64
Example 253b8888884864264
Example 25448848248464
Example 254b4484884641664
Example 255>0.5>0.5>0.5>0.5>64>6416>0.5>0.50.5>0.5
Staphylococcus
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusaureus-
NUMBERaureus (GC 1131)aureus (GC 3051)aureus (GC 3053)aureus (GC 4535)aureus (GC 4541)aureus (GC 4542)aureus (GC 4544)aureus (GC 4545)aureus (ATCC 29213)SMITH (GC 4536)
Example 255a>0.50.50.5>0.5>0.5>0.5>0.5>0.5
Example 256>64>64>64>64>64>64
Example 256a>64>64>64>64>64>64
Example 2570.50.50.50.50.50.50.50.5
Example 257a0.50.50.50.50.50.50.50.5
Example 257b0.50.50.50.50.50.50.50.5
Example 261a>64>64>64>64>64>64
Example 261b1616168168
Example 261c888888
Example 262a12864>128646464
Example 262b422424
Example 263646464>646464
Example 264a1616168816
Example 264b888848
Example 265a32161681616
Example 265b32888816
Example 270a444444
Example 270b888848
Example 271a448844
Example 277a>128>128>128>128>128>128>128>128
Example 277b>64>64>64>64>64>64>64>64
Example 277c>64>64>64>64>64>64>64>64
Example 278b84888848
Example 278c82844444
Example 279a>64>64>64>64>64>64>64>64
Example 280a>128>128>128>128>128>128>128>128
Example 280b>128128>12812812812864128
Example 282>128>128>128>128>128>128>128>128
Example 283a64641286464646464
Example 283b64641281286412864128
Example 283c3232643232321632
Example 284b>128>128>128>128>128>128>128>128
Example 287>64>64>64>64>64>64>64>64
Example 296>128>128>128>128>128>128>128>128
CoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulaseCoagulase
NegativeNegativeNegativeNegativeNegativeNegativeNegativeNegative
EXAMPLEStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcusStaphylococcus
NUMBERaureus-SMITH (GC 4543)haemolyticus (GC 4546)(GC 4537)(GC 4538)(GC 4547)(GC 4548)(GC 4549)(GC 4551)(GC 6257)(ID-3941)
Example 255a>0.56464>6464>6464
Example 256>64>64>64>64>64>64>64
Example 256a>64>64>64>64>64>6464
Example 2570.5222281
Example 257a0.58888324
Example 257b0.5222241
Example 261a>64>64>64>64>64>64
Example 261b888448
Example 261c8444416
Example 262a6464646416128
Example 262b122112
Example 263323264321664
Example 264a8884416
Example 264b844448
Example 265a888848
Example 265b888448
Example 270a422224
Example 270b444444
Example 271a844244
Example 277a>128>128>128>128>128>128
Example 277b>64>64>64>64>64>64>64
Example 277c>64>64>64>64>64>64>64
Example 278b8444282
Example 278c4242282
Example 279a>646464>6464>6464
Example 280a>128128128>128128>128128
Example 280b6432321283212832
Example 282>128>128>128>128>128>128
Example 283a646464643264
Example 283b646464646464
Example 283c16161681632
Example 284b>128>128>128>128>128>128
Example 287>64>64>64>64>64>64>64
Example 296>128>128>128>128>128>128
StreptococcusStreptococcusStreptococcusStreptococcusStreptococcusStreptococcus
EXAMPLEagalactiaepneumoniaepneumoniaepneumoniaepyogenespyogenesEnterococcusEnterococcusEnterococcusEnterococcus
NUMBER(GC 4564)(GC 1894)(GC 4565)(ATCC 6301)(GC 4563)(ID-3187)faecalis (GC 2242)faecalis (GC 2691)faecalis (GC 3059)faecalis (GC 4552)
Example 255a643232>0.5>0.5>0.5>0.5
Example 256>64>6464>64>64
Example 256a>646464>64>64
Example 25720.2510.250.120.50.50.5>0.5
Example 257a81410.12>0.50.5>0.5>0.5
Example 257b10.250.50.250.120.50.50.5>0.5
Example 261a>64>64>64>64
Example 261b846464
Example 261c443264
Example 262a3232>128>128
Example 262b111632
Example 2633232>64>64
Example 264a8464>64
Example 264b443264
Example 265a4464>64
Example 265b846464
Example 270a111616
Example 270b221632
Example 271a421632
Example 277a>128>128>128>128>128>128>128>128>128
Example 277b>64>64>64>64>64>64>64>64>64
Example 277c>64>64>64>64>64>64>64>64>64
Example 278b4121232326432
Example 278c20.511116323232
Example 279a>6464>646464>64>64>64>64
Example 280a>128128>128>128>128>128>128>128>128
Example 280b128641283264>128>128>128>128
Example 282>128128>128128>128>128>128>128>128
Example 283a6416161664128>128>128>128
Example 283b6416323264128>128>128>128
Example 283c1648816128128>128128
Example 284b>128128>128>128>128>128>128>128>128
Example 287>64646464>64>64>64>64>64
Example 296>128128>128>128>128>128>128>128>128
EnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcusEnterococcus
EXAMPLEfaecalisfaecalisfaecalisfaecalisfaeciumfaeciumfaeciumaviumEscherichiaEscherichiaEscherichia
NUMBER(GC 4553)(GC 4554)(GC 6189)(ATCC 29212)(GC 2243)(GC 4556)(GC 4557)(GC 4558)coli (GC 4559)coli (GC 4560)coli (ATCC 25922)
Example 255a>0.5>0.5>0.5>0.5>64>6432>0.5>0.50.5>0.5
Example 256>64>64>64>64>6464>64>6432>64
Example 256a>64>64>64>64>6432>64>648>64
Example 2570.5>0.50.50.5161620.5>0.50.5>0.5
Example 257a>0.5>0.5>0.5>0.5>32>328>0.5>0.50.5>0.5
Example 257b0.5>0.50.50.5161620.5>0.50.5>0.5
Example 261a>64>64>64>64>64>64>64>64>64>64
Example 261b64>64>64>64641664>644>64
Example 261c6464646464864>644>64
Example 262a>128>128>128>128>128>128>128>12816>128
Example 262b3232321616216>641>64
Example 263>64>64>64>64>6432>64>6416>64
Example 264a>64>6464>646432>64>64464
Example 264b6464646464864>64464
Example 265a>64>6464>6464864>644>64
Example 265b64>64646464864644>64
Example 270a1632161616416>642>64
Example 270b3232323232832>644>64
Example 271a3232323264432>64264
Example 277a>128>128>128>128>128>128128128>128>128>128
Example 277b>64>64>64>64>64>64>64>64>6432>64
Example 277c>64>64>64>64>64>64>64>64>64>64>64
Example 278b323232323232832>644>64
Example 278c323232323232832>642>64
Example 279a>64>64>64>64>64>6464>64643264
Example 280a>128>128>128>128>128>128>128>1286464128
Example 280b>128>128>128>128128>12864128163232
Example 282>128>128>128>128>128>128128128>128128>128
Example 283a>128>128>128>128>128>12864128>12832128
Example 283b>128>128>128>128>128>12864128>12832>128
Example 283c128>128128128128128161281288128
Example 284b>128>128>128>128>128>128128128>128>128>128
Example 287>64>64>64>64>64>646464>64>64>64
Example 296>128>128>128>128>128>128128128>128>128>128

Zone of Inhibition

Protocol for Assay Plate Staphylococcus aureus

Inoculate 10 mL of Tryptic Soy Broth with a loopful of slant culture, Staphylococcus aureus, and place in a stationary rack at 37° C. After 16-18 hour incubation, the Optical Density (OD) of the culture is read @ A600 nm, using a 1:10 dilution. OD should be between 0.1-0.3, and if not adjust with Tryptic Soy Broth. A 40 mL sample of Nutrient Agar, pH 6.8 is inoculated with 90 μl of S. aureus culture and poured into a sterile petri dish. When the agar has solidified, wells (5 mm) are plated using an automated welling device. Wells are inoculated with 25 μl of extract and incubated overnight at 37° C. Zones of inhibition are measured and recorded the following morning. The results of representative examples of the invention are given in Table 3.

TABLE 3
Zone of Inhibition vs.
Example No.S. aureus (mm)
270c11
271c12
272b8
8
273b8
9
274a9
274b10

Methods for in Vivo Antibacterial Evaluation

The therapeutic effects of glycopeptide antibiotics of Formula I are determined against acute lethal infections with S. aureus (strain Smith), a penicillin resistant strain of S. pneumoniae (strain GC 1894), and a vancomycin resistant strain of E. fecalis (strain GC 6189 and GC 2246). Female mice, CD-1 (Charles River Laboratories), 20±2 gm, are challenged by intraperitoneal injection of sufficient bacteria (suspended in Trypticase Soy Broth or hog gastric mucin) to kill non-treated controls within 24-48 hr. Antibacterial agents, contained in 0.2 mL of saline or 5% dextrose solution, are administered intravenously 30 min. after infection. Five mice are treated at each dose level. The 7 day survival ratios from 3 separate tests are pooled for calculation of median effective dose (ED50). The results of representative examples of the invention are given Table 4.

TABLE 4
In Vivo Antibacterial Activity of Glycopeptide Antibiotics
in Acute Lethal Infections in Mice
Staphylococcus
EX-EnterococcusEnterococcusaureus-Streptococcus
AM-faecalisfaecalisSMITHpneumoniae
PLE(GC 2246)(GC 6189)(GC 4543)(GC 1894)
 288
 52>4
 55>8
 59>8
 60>8
 61>8
 62>8
 64>8
 65>8
 66>8
 66a>4
 67>8
 69>8
 71>8
 72>8
 73>8
 74>8
 774
 782
 80>8
 81>8
 89>8
 95b4
 96c5.20.29
 97b8
 99c4.30.52
1021.040.23-0.43
1030.28
1040.39-0.630.190.22
105 1.8-1.960.04-0.080.04
1060.07
1110.280.140.03
1120.19-0.280.07-0.080.02
1131.040.26
1150.360.23
1160.460.08-0.19
1170.380.26-0.5 
1190.410.19
1200.06
1210.50.32
1350.260.07
1370.24
141>8
1430.28
1540.1
1580.14
1740.08
1770.1
1800.05
2190.5
2200.19
2210.03
2300.12
230a0.06
2310.25
231a0.06
2350.59
2454
245a1
262b1.22
263>8
277a>8
277b>8
277c>8
280a>8
280b>8

Table 5

In Vivo Antibacterial Activity of Glycopeptide Antibiotics in Non-Lethal Thigh Infections in Mice

The therapeutic effects of glycopeptide antibiotics of the invention are also determined against a non-lethal thigh infection model in mice infected with S. aureus (strain Smith and PT 5679), a penicillin resistant strain of S. pneumoniae (strain GC 1894), a penicillin sensitive strain of S. pneumoniae (GC 6242), and a vancomycin resistant strain of E. fecalis (strain GC 6189). Female mice, CD-1 (Charles River Laboratories), 20±2 gm, are challenged by intramuscular injection of sufficient bacteria (suspended in Trypticase Soy Broth or hog gastric mucin) to cause biohazard class 1-2 (Biosafety in Microbiological and Medical Laboratories, HHS Publication NO (NIH) 88-8395, 3rd edition, 1993) infection in mice. Broth cultures of freshly plated bacteria are grown into log phase overnight to an optical density of 0.3 at 580 nm. After a 1:10 dilution into fresh broth, 0.1 mL (approximately 106 CFU) is injected intramuscularly into the thigh of each mouse. Antibacterial agents, contained in 0.2 mL of saline or 5% dextrose solution, are administered intravenously beginning 2 hr after infection. Two-fold serial dilutions of each antibiotic are administered at selected time intervals for up to 22 hr post-infection to achieve a range of drug concentrations in serum for a complete dose-response relationship from no effect to maximal effect. After 24 hr. animals are sacrificed, thighs are removed and homogenized in 10 mL of 0.85% iced saline. Duplicate aliquots are plated for serial dilutions to determine the bacterial population. Efficacy is calculated by subtracting the log10 CFU per thigh of untreated control mice just before therapy and at the end of therapy (24 hr) from the treated groups. The results of representative examples of the invention are given in Table 5.

TABLE 5
In Vivo Antibacterial Activity of Glycopeptide
Antibiotics in Mouse Thigh Infection
EnterococcusStaphylococcusStreptococcusStreptococcus
faecalisStaphylococcusaureus-pneumoniaepneumoniae
EXAMPLE(GCaureusSMITH(GC(GC
NO.6189)(PT 5679)(GC 4543)1894)6242)
7610.63 
1020.5 2.03
1041.22-1.8 1.42
1051  2.461.02-1.840.53
1060.59
1110.481.73-2 
1120.33-0.651.57-1.950.13
1131.25
1150.56-1.371.22
1161.21-1.651.1-1.9
1170.672.53
1191.391.15
1351.021.27
1371.190.87

Clinical Pathology:

20-day-old CD-1 mice were divided into a vehicle control group (5 mice) and a treatment group (5 mice). Samples of glycopeptide antibiotics were administered at 20 mg/kg intravenously daily for 9 days. Animals were necropsied on day 10 Sera were analyzed for BUN (blood urea nitrogen), creatinine, AST (aspartic aminotransferase), and ALT (alanine aminotransferase) by routine, standard, automated methods using an Hitachi 747 chemistry analyzer. Results of representative examples of the invention are given in Table 6.

Anatomic Pathology:

Samples of tissues from necropsied mice were formalin-fixed, paraffin-embedded, sectioned, stained with hematoxylin and eosin, and examined microscopically. Histopathologic findings were recorded. These findings were subjectively graded on a scale corresponding to slight, mild, moderate, marked and severe as compared to untreated controls. Results of representative examples of the invention are given in Table 6.

TABLE 6
Clinical Chemistry and Anatomical Pathology Comparison
in Mice
Results based on 20 mg/kg Intravenous Dose
ClinicalAnatomical
Chemistry (Day 10)Pathology
% of Control(Day 10)
Ex. No.ASTALTBUNCreatinineHeartbKidney
 28No samples00
 52NSNS  211%NS0+++
 59NSNSNSNS00
 60NSNSNSNS00
 61NSNS+157%+122%0+++
 62NT*NT*NT*
 64NSNSNSNS00
 65+182%+196%+161%NS0+++
 66  147%  182%NSNS00
 66aNSNSNSNS0++
 67NSNSNSNS00
 69NSNSNSNS00
 71NSNSNSNS00
 72NSNS+122%NS0++
 73NT*NT*NT*
 74NSNSNSNS00
 76NSNSNSNS0++
 77NSNSNSNS00
 78NSNSNSNS0++
 80NT*NT*NT*
 81NSNSNSNS00
102+340%+672%+249%+100%++++++
104 +87%NS+203% +65%++++++
105+205%+480% +35%NS++++++
106NSNSNSNS0+/−
141NSNS+308%+113%0+++
219NSNSNSNS0+++
220NSNS  149%  121%0+++
221NSNSNSNS00
230NSNS+179%+124%0+++
230aNSNSNSNS0+
245NSNS+160%+138%0+++
245aNSNS+212%+133%++++
263NSNSNS+116%+++
277aNSNS+110%NS0++
277b+138%+164%+113%NS0+
277c+253%NSNSNS0+
280aNSNSNSNS0++
280bNT*NT*NT*

aClinical chemisitry-Liver function tests included AST and ALT measurements.

Renal function tests includes BUN and Creatinine measurements

Degree of elevation reported as a % above untreated control animals.

bAnatomical Pathology-Heart and kidneys were examined for microscopic histopathology

Degree of severity and number of animals affected were scored by 0, +, ++, or +++ as compared to untreated control animals.

NS—not significant change from controls.

NT*—animals did not survive treatment regimin.

In therapeutic use, the compounds of this invention may be administered in the form of conventional pharmaceutical composition appropriate for the intended use as antibacterials. Such compositions may be formulated so as to be suitable for oral, parenteral or topical administration. The active ingredient may be combined in admixture with nontoxic pharmaceutical carrier may take a variety of forms, depending on the form of preparation desired for administration, i.e. oral, parenteral, or topical.

When the compounds are employed as antibacterials, they can be combined with one or more pharmaceutically acceptable carriers, for example, solvents, diluentsand the like, and may be administered orally in such forms as tablets, capsules, dispersible powders, granules, or suspensions containing, for example, from about 0.05 to 5% of suspending agent, syrups containing, for example, from about 10 to 50% of sugar, and elixirs containing for example, from about 20 to 50% ethanol and the like, or parenterally in the form of sterile injectable solutions or suspensions containing from about 0.05 to 5% suspending agent in an isotonic medium. Such pharmaceutical preparations may contain, for example, from about 25 to about 90% of the active ingredient in combination with the carrier, more usually between about 5% and 60% by weight.

An effective amount of compound from 0.001 mg/kg of body weight to 100.0 mg/kg of body weight should be administered one to five times per day via any typical route of administration including but not limited to oral, parenteral (including subcutaneous, intravenous, intramuscular, intrasternal injection or infusion techniques), topical or rectal, in dosage unit formulations containing conventional non-toxic pharmaceutically acceptable carriers, adjuvants and vehicles. It will be understood, however, that the specific dose level and frequency of dosage for any particular patient may be varied and will depend upon a variety of factors including the activity of the specific compound employed, the metabolic stability and length of action of that compound, the age, body weight, general health, sex, diet, mode and time of administration, rate of excretion, drug combination, the severity of the particular condition of the host undergoing therapy.

Additionally, the antibacterially effective amount of the glycopeptide antibiotics of the invention may be administered at a dosage and frequency without inducing side effects commonly experienced with conventional antibiotic therapy which could include hypersensitivity, neuromuscular blockade, vertigo, photosensitivity, discoloration of teeth, hematologic changes, gastrointestinal disturbances, ototoxicity, and renal, hepatic, or cardiac impairment. Further the frequency and duration of dosage may be monitored to substantially limit harmful effects to normal tissues caused by administration at or above the antibacterially effective amount of the glycopeptide antibiotics of the invention.

These active compounds may be administered orally as well as by intravenous, intramuscular, or subcutaneous routes. Solid carriers include starch, lactose, dicalcium phosphate, microcrystalline cellulose, sucrose and kaolin, while liquid carriers include sterile water, polyethylene glycols, non-ionic surfactants and edible oils such as corn, peanut and sesame oils, as are appropriate to the nature of the active ingredient and the particular form of administration desired. Adjuvants customarily employed in the preparation of pharmaceutical compositions may be advantageously included, such as flavoring agents, coloring agents, preserving agents, and antioxidants, for example, vitamin E, ascorbic acid, BHT and BHA. These active compounds may also be administered parenterally or intraperitoneally. Solutions or suspensions of these active compounds as a free base or pharmacologically acceptable salt can be prepared in glycerol, liquid, polyethylene glycols and mixtures thereof in oils. Under ordinary conditions of storage and use,these preparations contain a preservative. The pharmaceutical forms suitable for injectable use include sterile aqueous solutions or dispersions and sterile powders for the extemporaneous preparation of sterile injectable solutions or dispersions. In all cases, the form must be sterile and must be fluid to the extent that easy syringability exists. It must be stable under the conditions of manufacture and storage and must be preserved against the contaminating action of microorganisms such as bacterial and fungi. The carrier can be a solvent or dispersion medium containing, for example, water, ethanol, polyol (e.g., glycerol, propylene glycol and liquid polyethylene glycol), suitable mixtures thereof, and vegetable oil.

The invention accordingly provides a pharmaceutical composition which comprises a compound of this invention in combination or association with a pharmaceutically acceptable carrier. In particular, the present invention provides a pharmaceutical composition which comprises an antibacterially effective amount of a compound of this invention and a pharmaceutically acceptable carrier.

The present invention further provides a method of treating bacterial infections in warm-blooded animals including man, which comprises administering to the afflicted warm-blooded animals an antibacterially effective amount of a compound or a pharmaceutical composition of a compound of the invention. The invention will be more fully described in conjunction with the following specific examples which are not to be construed as limiting the scope of the invention.

The following examples illustrate the preparation of the compounds of the invention by fermentation and synthetic procedures and as such are not to be considered as limiting the invention set forth in the claims appended hereto.

EXAMPLE 1

Cyclo[glycyl-β-methylphenylalanyl-3-bromo-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl- 2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (152 mg) in trifluoroacetic acid (4 mL) is treated with N-bromosuccinimide (23 mg) and the reaction mixture is then stirred at room temperature for 2 h. Volatiles are then removed in vacuo and the resulting residue is triturated with ether, the solid collected and washed with ethyl acetate and then diethyl ether to give the crude monobromo-derivative of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl]. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 687 (M+2H)2+.

EXAMPLE 2

Cyclo[glycyl-β-methylphenylalanyl-3-bromotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl ]

A stirred solution the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (21 mg) in trifluoroacetic acid (0.5 mL) is treated with 3 mg of bromine in 0.3 mL of acetic acid and the reaction is stirred at room temperature for 45 min, then poured into diethyl ether (8 mL). The resulting solid is collected by filtration and washed with diethyl ether to give 18 mg of the crude monobromo-derivative of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 525.1 (M+2H)2+.

EXAMPLE 3

Cyclo[glycyl-β-methylphenylalanyl-3,5-dibromotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryls eryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (31 mg) in trifluoroacetic acid (1 mL) is treated with N-bromosuccinimide (10 mg) and the reaction mixture is then stirred at room temperature for 2 h. Volatiles are then removed in vacuo and the resulting residue is triturated with ether, the solid collected and washed with ethyl acetate and then diethyl ether to give the crude dibromo-derivative of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 565 (M+2H)2+.

EXAMPLE 4

Cyclo[glycyl-β-methylphenylalanyl-3,5-dibromotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 3. MS (+ES), m/z: 484 (M+2H)2+.

EXAMPLE 5

Cyclo[glycyl-β-methylphenylalanyl-3-iodotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (31 mg) in trifluoroacetic acid (1 mL) is treated with N-iodosuccinimide (12 mg) and the reaction mixture is then stirred at 4-8° C. for 2 h. Volatiles are then removed in vacuo and the resulting residue is triturated with ether, the solid is collected by filtration and washed with ethyl acetate and then diethyl ether to give the crude monoiodo-derivative of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 549 (M+2H)2+.

EXAMPLE 6

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)-3-iodo-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl- 2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 5 using the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl]. MS (+ES), m/z: 711.3 (M+2H)2+.

EXAMPLE 7

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)-3,5-diiodo-tyrosyl-3-(2-iminioimidazolidin-4-yl)seryl-3-(3-hexopyran osyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (304 mg) in trifluoroacetic acid (10 mL) is treated with N-iodosuccinimide (99 mg) and the reaction mixture is then stirred at 4-8° C. for 2 h. Volatiles are then removed in vacuo and the resulting residue is triturated with ether, the solid collected and washed with ethyl acetate and then diethyl ether to give the crude diiodo-derivative of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl]. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 774 (M+2H)2+.

EXAMPLE 8

Cyclo[glycyl-β-methylphenylalanyl-3-nitrotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl ]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (4.62 g) in trifluoroacetic acid (10 mL) at 3° C. is treated with potassium nitrate (492 mg) and the reaction mixture is then stirred with cooling in an ice bath for 45 min. Volatiles are then removed in vacuo and the resulting residue is triturated with ethanol to provide an amber solid, which is then collected by filtration and washed with ethanol and then diethyl ether to give the crude mono-nitro derivative of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 508 (M+2H)2+.

EXAMPLE 9

Cyclo[glycyl-β-methylphenylalanyl-3-nitrotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 8. MS (+ES), m/z: 427.8 (M+2H)2+.

EXAMPLE 10

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-3-nitrotyros yl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyltyrosyl] by the procedure described for example 8. MS (+ES), m/z: 492.9 (M+2H)2+.

EXAMPLE 11

Cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl ]

A stirred solution of the crude bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-nitrotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (16 g) in 15% aqueous acetic acid (160 mL) and ethanol (10 mL) is hydrogenated under balloon pressure at room temperature over 10% palladium on carbon (1.2 g) for 3.5 h. The catalyst is then removed by filtration through diatomaceous earth, the filtrate is concentrated to a volume of ˜70 mL, then added to acetonitrile (450 mL) and the precipitated product is collected by filtration. The precipitate is then washed with acetonitrile and diethyl ether and air dried to give the desired product. MS (+ES), m/z: 493.9 (M+2H)2+.

EXAMPLE 12

Cyclo[glycyl-β-methylphenylalanyl-3-(dimethylamino)tyrosyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl )serylseryl]

A stirred solution of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (100 mg) in ethanol (10 mL) is treated with glacial acetic acid (1.5 mL) and aqueous formaldehyde (37%, 1 mL), and is then hydrogenated under balloon pressure at room temperature over 10% palladium on carbon for 1 hour. The catalyst is removed by filtration through diatomaceous earth, and the filtrate is concentrated to a volume of ˜4 mL. The concentrated filtrate is then added to acetonitrile (15 mL) and diethyl ether (30 mL) and the precipitated product is collected by filtration. The precipitate is then washed with acetonitrile and diethyl ether and air dried to give the desired product. MS (+ES), m/z: 507.8 (M+2H)2+.

EXAMPLE 13

Cyclo[glycyl-β-methylphenylalanyl-3-acetamidotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolodin-4-yl)seryls eryl]

A stirred solution of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (100 mg) in neat acetic anhydride (0.2 mL) is stirred at room temperature for 45 min. Acetic, anhydride is removed under a stream of nitrogen and the residue is triturated with diethyl ether. The resulting precipitate is collected by filtration, washed, and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 515 (M+2H)2+.

EXAMPLE 14

Cyclo[glycyl-β-methylphenylalanyl-3-(propanamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)se rylseryl]

A stirred solution of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (100 mg) in tetrahydrofuran (0.2 mL) is treated with propionic anhydride (2 mL) and the reaction mixture is stirred at room temperature for 75 min. The reaction mixture is then triturated with acetonitrile and diethyl ether, and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. MS (+ES), m/z: 522.2 (M+2H)2+.

EXAMPLE 15

Cyclo[glycyl-β-methylphenylalanyl-3-(2-methylpropanamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin -4-yl)serylseryl]

The title compound is prepared by the procedure described for example 14 using isobutyric anhydride to give the corresponding isobutyryl amide derivative. MS (+ES), m/z: 528.9 (M+2H)2+.

EXAMPLE 16

Cyclo[glycyl-β-methylphenylalanyl-3-(heptanamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)se rylseryl]

The title compound is prepared by the procedure described for example 14 using heptanoic anhydride to give the corresponding heptyl amide derivative. MS (+ES), m/z: 550.2 (M+2H)2+.

EXAMPLE 17

Cyclo[glycyl-β-methylphenylalanyl-3-(benzamido)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)sery lseryl]

A stirred solution of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (250 mg) in tetrahydrofuran (3 mL) is treated with benzoyl chloride (0.3 mL) and the reaction mixture is then stirred at room temperature for 45 min. Solvent is removed under a stream of nitrogen and the residue is triturated with diethyl ether. The resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 545.9 (M+2H)2+.

EXAMPLE 18

Cyclo[glycyl-β-methylphenylalanyl-3-formamidotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryls eryl]

A stirred suspension of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (180 mg) in 88% formic acid (2.5 mL) at 0° C. is treated with acetic anhydride (0.25 mL) and the reaction mixture is then stirred for 45 min. The reaction mixture is then diluted with diethyl ether and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 508.5 (M+2H)2+.

EXAMPLE 19

Cyclo[glycyl-β-methylphenylalanyl-3-[[(4-methylphenoxy)carbonyl]amino]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-imin oimidazolidin-4-yl)serylseryl]

A stirred suspension of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (61 mg) in glacial acetic acid (5 mL) is treated dropwise with a solution of p-tolyl chloroformate (8.5 mg) in glacial acetic acid (0.5 mL) and the reaction mixture is then stirred at 70° C. for 2 h. The reaction mixture is then diluted with diethyl ether and acetonitrile and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 561 (M+2H)2+.

EXAMPLE 20

Cyclo[glycyl-β-methylphenylalanyl-3-[(methoxycarbonyl)amino]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazoli din-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 19 using methyl chloroformate to form the corresponding urethane derivative. MS (+ES), m/z: 523.5 (M+2H)2+.

EXAMPLE 21

Cyclo[glycyl-β-methylphenylalanyl-3-[(phenylmethoxycarbonyl)amino]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimi dazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 19 using benzyl chloroformate to form the corresponding urethane derivative. MS (+ES), m/z: 561 (M+2H)2+.

EXAMPLE 22

Cyclo[3-(2,3-dihydro-2-oxo-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryl serylglycyl-β-methylphenylalanyl]

A stirred suspension of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (106 mg) in glacial acetic acid (9.5 mL) is treated dropwise with a solution of 4-chlorophenyl chloroformate (17 mg) in glacial acetic acid (0.5 mL) and the reaction mixture is then stirred at 70° C. for 3 h. The reaction mixture is then diluted with diethyl ether and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The resulting solid (71 mg) is dissolved in 0.1N NaOH (2 mL) and stirred at room temperature for 1 h. The solution is then diluted with acetonitrile and the resulting precipitate is collected by filtration, washed with acetonitrile then diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 507 (M+2H)2+.

EXAMPLE 23

Cyclo[3-(2,3-dihydro-2-thio-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)sery lserylglycyl-β-methylphenylalanyl]

A stirred solution of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (177 mg) in N,N-dimethylformamide (3 mL) is treated with 1,1′-thiocarbonyldiimidazole (32 mg) and the mixture is stirred at room temperature for 1 h. The reaction mixture is then diluted with diethyl ether and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 515 (M+2H)2+.

EXAMPLE 24

Cyclo[glycyl-β-methylphenylalanyl-3-[[[3,5-bis(trifluoromethyl)phenyl]carbamothioyl]amino]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

A stirred suspension of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (135 mg) in THF (0.5 mL) is treated with 3,5-ditrifluoromethylphenyl isothiocyanate (0.6 mL) and the mixture is stirred at room temperature for 3 days. The reaction mixture is then diluted with diethyl ether and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 629.2 (M+2H)2+.

EXAMPLE 25

Cyclo[3-[2-(4-carboxyphenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)ser ylserylglycyl-β-methylphenylalanyl]

A stirred suspension of the bis-trifluroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (121 mg) in N,N-dimethylformamide (5 mL) at room temperature is treated with 4-carboxybenzaldehyde (75 mg) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (57 mg), and the reaction mixture is stirred for 2 h. The reaction mixture is then poured into a mixture of diethyl ether and acetonitrile, and the resulting solid is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 558.7 (M+2H)2+.

EXAMPLE 26

Cyclo[3-[2-(3-nitrophenyl)-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryl serylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 559.5 (M+2H)2+.

EXAMPLE 27

Cyclo[3-[2-(4-bromophenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)seryl serylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 576.6 (M+2H)2+.

EXAMPLE 28

Cyclo[3-[2-[3-(4-methylphenoxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3hexopyranosyl-2-iminoimidazolidin -4-yl)serylserylglycyl-β-methylphenyl-alanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 590.2 (M+2H)2+.

EXAMPLE 29

Cyclo[3-[2-[4-(dimethylamino)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin -4-yl)serylserylglycyl-β-methylphenyl-alanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 558.6 (M+2H)2+.

EXAMPLE 30

Cyclo[3-[2-(3-fluorophenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)sery lserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 545.8 (M+2H)2+.

EXAMPLE 31

Cyclo[3-[2-[4-(phenylmethoxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl-β-methyl-phenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 589.9 (M+2H)2+.

EXAMPLE 32

Cyclo[3-[2-(4-tert-butylphenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl) serylserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 565 (M+2H)2+.

EXAMPLE 33

Cyclo[3-[2-([1,1-biphenyl]-4-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-y l)serylserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 574.9 (M+2H)2+.

EXAMPLE 34

Cyclo[3-[2-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4 -yl)serylserylglycyl-β-methylphenyl-alanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 581.9 (M+2H)2+.

EXAMPLE 35

Cyclo[3-[2-[3-(4-methoxyphenoxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolid in-4-yl)serylserylglycyl-β-methylphenyl-alanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 597.9 (M+2H)2+.

EXAMPLE 36

Cyclo[3-[2-[2-(hexolpyranosyloxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazoli din-4-yl)serylserylglycyl-β-methyl-phenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 625.6 (M+2H)2+.

EXAMPLE 37

Cyclo[3-[2-(9H-fluoren-2-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)ser ylserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 581.6 (M+2H)2+.

EXAMPLE 38

Cyclo[3-[2-(3-furyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylg lycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 531.9 (M+2H)2+.

EXAMPLE 39

Cyclo[3-[2-(2,2-diphenylethenyl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl )serylserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 588.1 (M+2H)2+.

EXAMPLE 40

Cyclo[3-[2-(2-methylprop-1-en-1-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4 -yl)serylserylglycyl-β-methylphenyl-alanyl]

The title compound is prepared by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 526.1 (M+2H)2+.

EXAMPLE 41

Cyclo[3-[2-[4-(3-methylphenoxy)phenyl]benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(2-iminoimidazolidin-4-yl)serylserylgly cyl-β-methylphenylalanyl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 508.7 (M+2H)2+.

EXAMPLE 42

Cyclo[3-[2-(9H-fluoren-2-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)al anylserylglycyl-β-methylphenylalanyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyltyrosyl] by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 564.9 (M+2H)2+.

EXAMPLE 43

Cyclo[3-[2-(6-methoxynaphth-2-yl)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-y l)serylserylglycyl-β-methylphenylalanyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyltyrosyl] by the procedure described for example 25 using the appropriate aldehyde to form the corresponding benzoxazole derivative. MS (+ES), m/z: 577.2 (M+2H)2+.

EXAMPLE 44

Cyclo[3-[[2-(2,3,4 6-tetra-O-benzoylhexopyranosyl)amino]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4- yl)seryl-serylglycyl-β-methylphenylalanyl]

A suspension of the bis-trifluoroacetate salt of cyclo[glycyl-β-methylphenylalanyl-3-aminotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (300 mg) in THF (5 mL) is treated with 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl isothiocyanate (300 mg) and the mixture is stirred at room temperature for 11 days. The reaction mixture is then diluted with diethyl ether and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The resulting solid is then dissolved in methanol (5 mL) and treated with mercuric chloride (350 mg) and the reaction mixture is stirred at room temperature for 18 h. Methanol is then evaporated under a gentle stream of nitrogen and the title compound is then isolated by reverse phase HPLC. MS (+ES), m/z: 795.9 (M+2H)2+.

EXAMPLE 45

Cyclo[3-[2-(benzylthio)-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylser ylglycyl-β-methylphenylalanyl]

A stirred solution of the bis-trifluoroacetate salt of cyclo[3-(2,3-dihydro-2-thio-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylse rylglycyl-β-methylphenylalanyl] (100 mg) in N,N-dimethylformamide (0.6 mL) is treated with benzyl bromide (40 mg) and N,N-diisopropylethylamine (40 uL), and the mixture is stirred at room temperature for 30 min. The reaction mixture is then diluted with diethyl ether and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 560 (M+2H)2+.

EXAMPLE 46

Cyclo[3-[2-[(naphthylmethyl)thiol-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4- yl)serylserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 45 using 2-(bromomethyl)naphthalene to form the corresponding 2-thiobenzoxazole derivative. MS (+ES), m/z: 584.8 (M+2H)2+.

EXAMPLE 47

Cyclo[3-[2-[(4-phenylbenzyl)thio]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-y l)serylserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 45 using 4-phenylbenzyl chloride to form the corresponding 2-thiobenzoxazole derivative. MS (+ES), m/z: 598 (M+2H)2+.

EXAMPLE 48

Cyclo[3-[2-[(2-oxo-2-phenylethyl)thio]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolid in-4-yl)serylserylglycyl-β-methylphenyl-alanyl]

A stirred solution of the bis-trifluoroacetate salt of cyclo[3-(2,3-dihydro-2-thio-1,3-benzoxazol-5-yl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylse rylglycyl-β-methylphenylalanyl] (100 mg) in N,N-dimethylformamide (3 mL) is treated with 2-bromo-acetophenone (200 mg), and the mixture is stirred at room temperature for 2 h. The reaction mixture is then diluted with diethyl ether and the resulting precipitate is collected by filtration, washed with diethyl ether and air dried. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 573.7 (M+2H)2+.

EXAMPLE 49

Cyclo[3-[2-[[2-(4-chlorophenyl)-2-oxoethyl]thio]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoi midazolidin-4-yl)serylserylglycyl-β-methylphenylalanyl]

The title compound is prepared by the procedure described for example 48 using 2-bromo-4′-chloroacetophenone to form the corresponding 2-thiobenzoxazole derivative. MS (+ES), m/z: 590.7 (M+2H)2+.

EXAMPLE 50

Cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolid in-4-yl)serylserylglycyl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylseryl] (10 g) in 10% aqueous acetic acid (300 mL) containing n-butanol (10 mL) is hydrogenated under balloon pressure over 3% rhodium on carbon (20 g) and monitored periodically by electrospray mass spectrometry until the majority of the starting material is consumed. Catalyst is removed by filtration through diatomaceous earth and the filtrate is concentrated in vacuo to provide a gum. This material is then triturated with 1:1 acetonitrile-diethyl ether (300 mL) and the resulting precipitate is filtered, washed with acetonitrile and diethyl ether, and air dried. MS (+ES), m/z: 644.3 (M+2H)2+.

EXAMPLE 51

Cyclo[3-cyclohexyl-2-aminobutanoyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-imino imidazolidin-4-yl)-serylserylglycyl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] by the procedure described for example 50. The product is then purified by reverse phase HPLC. MS (+ES), m/z: 651.1 (M+2H)2+.

EXAMPLE 52

Cyclo[3-cyclohexylalanyl-3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycy l]

EXAMPLE 52a

Cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylserylglycyl]

EXAMPLE 52b

Cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylserylglycyl]

A solution of the bis-hydrochloride salt of cyclo[glycylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylseryl] (350 mg) in 10% aqueous acetic acid (10 mL) containing n-butanol (1 mL) is hydrogenated over 3% Rh/C (250 mg) in a Parr apparatus at an initial pressure of 50 psi and monitored periodically by electrospray mass spectrometry until the starting material has been completely converted to products of the desired molecular weight. Catalyst is removed by filtration through diatomaceous earth and the filtrate is concentrated in vacuo to provide a gum. This material is then subjected to reverse phase HPLC separation to provide the three title compounds. Cyclo[3-cyclohexylalanyl-3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]: MS (+ES), m/z: 477.1 (M+2H)2+; Cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylserylglycyl]: MS (+ES), m/z: 647.1 (M+2H)2+; Cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylserylglycyl]: MS (+ES), m/z: 647.2 (M+2H)2+.

EXAMPLE 53

Cyclo[3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cyclohexyl-2-am inobutanoyl]

EXAMPLE 53a

Cyclo[3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidi n-4-yl)serylserylglycyl-3-cyclohexyl-2-aminobutanoyl]

The title compounds are prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] by the procedure described for example 52. Cyclo[3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cyclohexyl-2-amino butanoyl]: MS (+ES), m/z: 484 (M+2H)2+; Cyclo[3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4 -yl)serylserylglycyl-3-cyclohexyl-2-aminobutanoyl]: MS (+ES), m/z: 654.1 (M+2H)2+.

EXAMPLE 54

Cyclo[3-(syn-4-hydroxycyclohexyl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3- cyclohexyl-2-aminobutanoyl]

EXAMPLE 54a

Cyclo[3-(anti-4-hydroxycyclohexyl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3 -cyclohexyl-2-aminobutanoyl]

The title compounds are prepared from cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 52. Cyclo[3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cyclohexyl-2-amino butanoyl]: MS (+ES), m/z: 484 (M+2H)2+; Cyclo[3-(syn-4-hydroxycyclohexyl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cyc lohexyl-2-aminobutanoyl]: MS (+ES), m/z: 492.5 (M+2H)2+. Cyclo[3-(anti-4-hydroxycyclohexyl)alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl-3-cy clohexyl-2-aminobutanoyl]: MS (+ES), m/z: 492.3 (M+2H)2+.

EXAMPLE 55

Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (10 g) in dimethyl sulfoxide (80 mL) is treated with concentrated hydrochloric acid (37%, 5 mL) and the mixture is heated at 60° C. for 20 hrs. The solution is then filtered to remove insoluble material and the filtrate is treated dropwise at 60° C. with acetonitrile (180 mL) to precipitate the product. The mixture is cooled to room temperature and the precipitate is removed by filtration, the filter cake is washed with acetonitrile and diethyl ether and air dried to provide the product as a tan powder. MS (+ES), m/z: 486.4 (M+2H)2+.

EXAMPLE 56

Cyclo[glycylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminomidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4 -yl)serylseryl] by the procedure described for example 55. MS (+ES), m/z: 479.5 (M+2H)2+.

EXAMPLE 57

Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl]

To a suspension of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (1.5 g) in water (60 mL) is added sodium periodate (616 mg) and the mixture is stirred for 5 h. at room temperature. Methanol (45 mL) is added, followed by sodium borohydride (326 mg) and the mixture is stirred for 16 h. The volume of the solution is adjusted to 150 mL by the addition of methanol, and then concentrated hydrochloric acid (37%, 9 mL) is added and the solution is stirred at 60° C. for 16 h. The solution is cooled and concentrated in vacuo to provide a gum, which is subjected to flash chromatography over a reverse phase support (MCI CHP20P) to provided the desired product. MS (+ES), m/z: 405.4 (M+2H)2+.

EXAMPLE 58

Cyclo[3-cyclohexylalanyl-3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)-serylserylglycyl]

The title compound is prepared from cyclo[3-cyclohexylalanyl-3-cyclohexylalanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl] by the procedure described for example 57. MS (+ES), m/z: 396.4 (M+2H)2+.

EXAMPLE 59

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-(2-iminoimidazolidin-4-yl)seryl-3-[1-benzyl-3-hexopyranosyl-2 -iminoimidazolidin-4-yl]serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (1.0 g) in dimethyl sulfoxide (25 mL) and water (4 mL) is treated with benzyl bromide (2.0 mL) and potassium carbonate (2.0 g) and the mixture is stirred for 2 h at room temperature. The reaction mixture is filtered and the filtrate is treated with acetonitrile (100 mL) to precipitate the crude product. The precipitate is filtered, washed with acetonitrile, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z: 693.3 (M+2H)2+.

EXAMPLE 60

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-(2-iminoimidazolidin-4-yl)seryl-3-[1-(4-tert-butylbenzyl)-3-h exopyranosyl-2-iminoimidazolidin-4-yl]-serylseryl]

EXAMPLE 60a

Di-N-(4-tert-butylbenzyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.5 g) in dimethyl sulfoxide (10 mL) and water (1 mL) is treated with 4-t-butylbenzyl bromide (0.8 g) and potassium carbonate (0.8 g) and the mixture is stirred for 3 h at room temperature. The reaction mixture is filtered and the filtrate is treated-with acetonitrile (100 mL) to precipitate the crude products. The precipitate is filtered, washed with acetonitrile, and air-dried. The desired products are purified by reverse phase HPLC. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-(2-iminoimidazolidin-4-yl)seryl-3-[1-(4-tert-butylbenzyl)-3-hexo pyranosyl-2-iminoimidazolidin-4-yl]-serylseryl]: MS (+ES), m/z: 721.4 (M+2H)2+; Di-N-(4-tert-butylbenzyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 794.5 (M+2H)2+.

EXAMPLE 61

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-hexopyranosyl-1-(12-hy droxydodecyl)-2-iminoimidazolidin-4-yl]-serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (1.0 g) in dimethyl sulfoxide (20 mL) and water (4 mL) is treated with 12-bromo-1-dodecanol (0.66 g) and potassium carbonate (0.8 g) and the mixture is stirred for 2 h at room temperature. The reaction mixture is filtered and the filtrate is treated with acetonitrile (100 mL) to precipitate the crude product. The precipitate is filtered, washed with acetonitrile, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z: 740.4 (M+2H)2+.

EXAMPLE 62

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[1,3-dibenzyl-2-(benzylimino)imidazolidin-4-yl]seryl-3-[1-b enzyl-2-(benzylimino)-3-hexopyranosylimidazolidin-4-yl]serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (1.0 g) in dimethyl sulfoxide (25 mL) and water (4 mL) is treated with benzyl bromide (2.0 mL) and potassium carbonate (2.0 g) and the mixture is stirred for 16 h at room temperature. Additional benzyl bromide (1.0 mL), potassium carbonate (0.6 g) and water (5 mL) is then added and the mixture is stirred for 20 h. The reaction mixture is filtered and the filtrate is treated with acetonitrile (180 mL) to precipitate the crude product. The precipitate is filtered, washed with acetonitrile, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z: 873.4 (M+2H)2+.

EXAMPLE 63

Cyclo[glycyl-O-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-butyl-3-hexopyranosyl- 2-iminoimidazolidin-4-yl]serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (1.0 g) in dimethyl sulfoxide (20 mL) and water (2.0 mL) is treated with 1-bromobutane (0.24 mL) and potassium carbonate (0.6 g) and the mixture is stirred for 24 h at room temperature. The reaction mixture is filtered and the filtrate is treated with acetonitrile to precipitate the crude product. The precipitate is filtered, washed with acetonitrile, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z: 676.4 (M+2H)2+.

EXAMPLE 64

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(1,3-dimethyl-2-(methylimino)imidazolidin-4-yl)seryl-3-[3-h exopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]-serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.8 g) in dimethyl sulfoxide (15 mL) and water (1.5 mL) is treated with methyl iodide (0.35 mL) and potassium carbonate (1.0 g) and the mixture is stirred for 16 h at room temperature. Additional benzyl bromide (1.0 mL), potassium carbonate (0.6 g) and water (5 mL) is then added and the mixture is stired for 20 h. The reaction mixture is filtered and the filtrate is treated with acetonitrile (180 mL) to precipitate the crude product. The precipitate is filtered, washed with acetonitrile, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z: 697.6 (M)2+.

EXAMPLE 65

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino -1-(2-phenylbenzyl)-imidazolidin-4-yl]-serylseryl]

The title compound is prepared by the procedure described for example 59 using the appropriate arylmethyl halide. MS (+ES), m/z. 731.6(M+2H)2+.

EXAMPLE 66

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[3-(4-phenylbenzyl)-2-[(4-phenylbenzyl)imino]imidazolidin-4 -yl]seryl-3-[3-hexopyranosyl-2-imino-1-(4-phenylbenzyl)-imidazolidin-4-yl]serylseryl]

EXAMPLE 66a

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino -1-(4-phenylbenzyl)-imidazolidin-4-yl]-serylseryl]

The title compound is prepared by the procedure described for example 60 using the appropriate arylmethyl halide. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[3-(4-phenylbenzyl)-2-[(4-phenylbenzyl)imino]imidazolidin-4-yl ]seryl-3-[3-hexopyranosyl-2-imino-1-(4-phenylbenzyl)-imidazolidin-4-yl]serylseryl]: MS (+ES), m/z: 897.6(M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino-1- (4-phenylbenzyl)-imidazolidin-4-yl]-serylseryl]: MS (+ES), m/z: 731.6(M+2H)2+.

EXAMPLE 67

Cyclo[glycyl-O-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-hexopyranosyl-2-imino- 1-(2-naphthylmethyl)-imidazolidin-4-yl]-serylseryl]

The title compound is prepared by the procedure described for example 59 using the appropriate arylmethyl halide. MS (+ES), m/z: 718.7(M+2H)2+.

EXAMPLE 68

Cyclo[glycyl-O-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino -1-(4-trifluoromethylbenzyl)-imidazolidin-4-yl]-serylseryl]

The title compound is prepared by the procedure described for example 59 using the appropriate arylmethyl halide. MS (+ES), m/z: 727.5(M+2H)2+.

EXAMPLE 69

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-(4-carboxybenzyl)-2-im ino-3-hexopyranosylimidazolidin-4-yl]-serylseryl]

EXAMPLE 69a

Di-N-(4-carboxybenzyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3(3- hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 69b

Tri-N-(4-carboxybenzyl)-Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 60 using the appropriate arylmethyl halide. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-(4-carboxybenzyl)-2-imino -3-hexopyranosylimidazolidin-4-yl]-serylseryl]: MS (+ES), m/z: 715.4(M+2H)2+; Di-N-(4-carboxybenzyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 782.4(M+2H)2+; Tri-N-(4-carboxybenzyl)-cCyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3- hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 849.2(M+2H)2+.

EXAMPLE 70

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-hexopyranosyl-2-imino- 1-(3-methyl-but-2-enyl)imidazolidin-4-yl]serylseryl]

The title compound is prepared by the procedure described for example 59 using the appropriate allylic halide. MS (+ES), m/z: 682.5(M+2H)2+.

EXAMPLE 71

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-heptyl-3-hexopyranosyl -2-iminoimidazolidin-4-yl]serylseryl]

The title compound is prepared by the procedure described for example 63 using the appropriate alkyl halide. MS (+ES), m/z: 697.4(M+2H)2+.

EXAMPLE 72

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-(10-carboxydecyl)-3-he xopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]

EXAMPLE 72a

Di-N-(10-carboxydecyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 61 using the appropriate alkyl halide. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-(10-carboxydecyl)-3-hexop yranosyl-2-iminoimidazolidin-4-yl]serylseryl]: MS (+ES), m/z: 740.7(M+2H)2+; Di-N-(10-carboxydecyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 832.9(M+2H)2+.

EXAMPLE 73

Cyclo[3-[1,3-benzyl-2-(benzylimino)imidazolidin-4-yl]alanyl-3-[1-benzyl-2-(benzylimino)-3-hexopyranosylimidazolidin-4-yl]alanylserylglycy l-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 62 using the appropriate alkyl halide. MS (+ES), m/z: 857.9 (M+2H)2+.

EXAMPLE 74

Cyclo[3-[1,3-dimethyl-2-(methylimino)imidazolidin-4-yl]alanyl-3-[3-hexopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]alanylserylgly cyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 64. MS (+ES), m/z: 681.7(M)2+.

EXAMPLE 75

Cyclo[glycyl-β-methylphenylalanyl-O-(methyl)tyrosyl-3-(1,3-dimethyl-2-(methylimino)imidazolidin-4-yl)seryl-3-[3-hexopyranosyl-1-methyl-2- (methylimino)imidazolidin-4-yl]-serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 64. MS (+ES), m/z: 542.6(M)2+.

EXAMPLE 76

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[2-(benzylimino)-3-hexopyranosylimidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 59. MS (+ES) m/z: 759.4 (M+2H)2+.

EXAMPLE 77

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[2-[1-(4-tert-butylbenzyl)-3-hexopyranosyl-2-imidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 59 using the appropriate arylmethyl halide. MS (+ES) m/z: 787.7 (M+2H)2+.

EXAMPLE 78

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[3-hexopyranosyl-2-imino-1-(2-naphthylmethyl)-imidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 59 using the appropriate arylmethyl halide. MS (+ES) m/z: 784.6 (M+2H)2+.

EXAMPLE 79

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[1,3-dibenzyl-2-(benzylimino)imid azolidin-4-yl]seryl-3-[1-benzyl-2-(benzylimino)-3-hexopyranosylimidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 62 using the appropriate arylmethyl halide. MS (+ES) m/z: 939.9 (M+2H)2+.

EXAMPLE 80

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(1-benzyl-3-hexopyranosyl-2-iminoimidazolidin-4-yl)alanylserylglycyl-O-methylphenylalanyl-O-[4 -O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methlphenylalanyl-O-[4-O-[4,6-O-(2 -adamantylidene)hexopyranosyl]-hexopyranosyl]tyrosyl] by the procedure described for example 59. MS (+ES) m/z: 743.6 (M+2H)2+.

EXAMPLE 81

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[1,3-dimethyl-2-(methylimino)imid azolidin-4-yl]seryl-3-[3-hexopyranosyl-1-methyl-2-(methylimino)imidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 64. MS (+ES) m/z: 763.6 (M)2+.

EXAMPLE 82

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[1-[(3,7-dimethylocta-2,6-dien-1-yl)-imino]-3-hexopyranosylimidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 59. MS (+ES) m/z: 782.5 (M+2H)2+.

EXAMPLE 83

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[1-heptyl-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 63 using the appropriate alkyl halide. MS (+ES) m/z: 763.5 (M+2H)2+.

EXAMPLE 84

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-[3-hexopyranosyl-2-(hexylimino)imidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 63 using the appropriate alkyl halide. MS (+ES) m/z: 756.5 (M+2H)2+.

EXAMPLE 85

Cyclo[3-[2-[2-(hexopyranosyloxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(1-benzyl-3-hexopyranosyl-2-iminoi midazolidin-4-yl)serylserylglycyl-β-methyl-phenylalanyl]

The title compound is prepared from cyclo[3-[2-[2-(hexopyranosyloxy)phenyl]-1,3-benzoxazol-5-yl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl-β-methyl-phenylalanyl] by the procedure described for example 59. MS (+ES) m/z: 671.0 (M+2H)2+.

EXAMPLE 86

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl -3-(2-iminoimidazolidin-4-yl)seryl-3-(2-decanoylimino-3-hexopyranosylimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.1 g) in N,N-dimethylformamide (1.5 mL) and 2,4,6-collidine (1.2 mL) is treated with decanoic anhydride (0.07 mL) and the mixture is stirred for 30 h at room temperature. The reaction mixture is then concentrated in vacuo to provide a gum, which is triturated with ethyl acetate to precipitate the crude product. The precipitate is filtered, washed with ethyl acetate, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z: 725.2 (M+2H)2+.

EXAMPLE 87

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-(3-met hyl-butyrylimino)-imidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 86 using the appropriate carboxylic acid anhydride. MS (+ES), m/z: 690.2 (M+2H)2+.

EXAMPLE 88

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-(2-ethyl-butyrylimino) -3-hexopyranosylimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 86 using the appropriate carboxylic acid anhydride. MS (+ES), m/z: 697.2 (M+2H)2+.

EXAMPLE 89

Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl]

A stirred solution of the, bis-acetate salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (0.2 g) in dimethyl sulfoxide (1.5 mL) is treated with N,N-diisopropylethylamine (0.105 mL) and a solution of N-(benzyloxycarbonyloxy)-succinimide (160 mg) in dimethyl sulfoxide (0.3 mL) and the mixture is stirred for 16 h at room temperature. Acetonitrile (8 mL) is then added to precipitate the crude product. The precipitate is filtered, washed with acetonitrile and diethyl ether, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z. 687.3 (M+2H)2+.

EXAMPLE 90

N-[(Phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (50 mg) in N,N-dimethylformamide (0.8 mL) is treated with N,N-diisopropylethylamine (0.013 mL) and N-(benzyloxycarbonyloxy)-succinimide (13 mg) and the mixture is stirred for 16 h at room temperature. Acetonitrile is then added to precipitate the crude product. The precipitate is filtered, washed with ethyl acetate, and air-dried. The desired product is purified by reverse phase HPLC. MS (+ES), m/z: 715.8 (M+2H)2+.

EXAMPLE 91

Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] by the procedure described for example 89. MS (+ES), m/z: 849.7 (M+2H)2+.

EXAMPLE 92

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(pyrimidin-2-ylimino)imidazolidin-4-yl]seryl-3-[3-hexopy ranosyl-2-imino-1-(pyrimidin-2-yl)imidazolidin-4-yl]serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.908 g) in dimethyl sulfoxide (20 mL) is treated with potassium carbonate (0.912 g) and 2-chloropyrimidine (0.756 g) and the mixture is stirred for 20 h at 50° C. The mixture is cooled to room temperature, decanted into acetonitrile (64 mL) and the resultant precipitate collected by centrifugation. The precipitate is resuspended in acetonitrile (64 mL) and recentrifuged. The resulting pale brown solid is purified by reverse phase HPLC. MS (+ES), m/z: 726.4 (M+2H)2+.

EXAMPLE 93

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(1,3-benzoxazol-2-ylimino)imidazolidin-4-yl]seryl-3-[1-( 1,3-benzoxaxol-2-yl)-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.908 g) in dimethyl sulfoxide (20 mL) is treated with potassium carbonate (0.912 g) and 2-chlorobenzoxazole (0.674 g) and the mixture is stirred for 4 h at room temperature. The reaction mixture is decanted into acetonitrile (64 mL) and the resultant precipitate collected by centrifugation. The precipitate is resuspended in acetonitrile (64 mL) and recentrifuged. The resulting pale brown solid is purified by reverse phase HPLC. MS (+ES), m/z: 765.3 (M+2H)2+.

EXAMPLE 94

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(1,3-benzothiazol-2-ylimino)imidazolidin-4-yl]seryl-3-[1 -(1,3-benzo-thiazol-2-yl)-2-imino-3-hexopyranosylimidazolidin-4-yl]serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.24 g) in dimethyl sulfoxide (5 mL) is treated with potassium carbonate (0.24 g) and 2-chlorobenzothiazole (0.297 g) and the mixture is stirred for 5 days at 35° C. The mixture is cooled to room temperature, decanted into acetonitrile (64 mL) and the resultant precipitate collected by centrifugation. The precipitate is resuspended in acetonitrile (64 mL) and recentrifuged. The resulting pale brown solid is purified by reverse phase HPLC. MS (+ES), m/z: 781.2 (M+2H)2+.

EXAMPLE 95

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-hexanoylhexopyran osyl)-2-iminoimidazolidin-4-yl]serylseryl]

EXAMPLE 95a

Cyclo[glycyl-β-methylphenylalanyl-O-(6-O-hexanoyl-4-O-hexopyranosylhexopyranosyl)-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyra nosyl-2-iminoimidazolidin-4-yl)-serylseryl]

EXAMPLE 95b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(6-O-hexanoylhexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyr anosyl-2-iminoimidazolidin-4-yl)-serylseryl]

A stirred solution of the bis-trifluoroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.38 g) in N,N-dimethylformamide (50 mL) and pyridine (0.4 mL) is treated dropwise with a solution of hexanoic anhydride (0.25 g) in N,N-dimethylformamide (2 mL) and the reaction mixture is stirred for 16 h at room temperature. The reaction is then quenched by the addition of methanol (100 mL), stirred for 30 min, and the volatiles are removed in vacuo. The resulting residue is purified by reverse phase HPLC to provide the title compounds. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-hexanoylhexopyranosy l)-2-iminoimidazolidin-4-yl]serylseryl]: MS (+ES), m/z: 697.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-(6-O-hexanoyl-4-O-hexopyranosylhexopyranosyl)-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranos yl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES), m/z: 697.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(6-O-hexanoylhexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyrano syl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES), m/z: 697.4 (M+2H)2+.

EXAMPLE 96

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-[6-O-(diphenylacetyl)h exopyranosyl]-2-iminoimidazolidin-4-yl]-serylseryl]

EXAMPLE 96a

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoi midazolidin-4-yl)seryl-O-(diphenylacetyl)-seryl]

EXAMPLE 96b

Cyclo[glycyl-β-methylphenylalanyl-O-[6-O-(diphenylacetyl)-4-O-hexopyranosylhexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 96c

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(diphenylacetyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3- hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-trifluoroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (1.0 g) in N,N-dimethylformamide (100 mL) and pyridine (1.0 mL) is treated dropwise with a solution of diphenylacetyl chloride (0.8 g) in N,N-dimethylformamide (2 mL) at −5° C. The resulting mixture is warmed to room temperature and stirred for 1 h. The reaction is then quenched by the addition of methanol (100 mL), stirred for 30 min, and the volatiles are removed in vacuo. The resulting residue is purified by reverse phase HPLC to provide the title comounds. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-[6-O-(diphenylacetyl)hexo pyranosyl]-2-iminoimidazolidin-4-yl]-serylseryl]: MS (+ES), m/z: 745.2 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)seryl-O-(diphenylacetyl)-seryl]: MS (+ES), m/z: 745.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[6-O-(diphenylacetyl)-4-O-hexopyranosylhexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexo pyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 745.3 (M+2H)2+. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(diphenylacetyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hex opyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 745.4 (M+2H)2+.

EXAMPLE 97

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexolpyranosylhexopyranosyl)tyrosyl- 3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-heptanoylhexopyranosyl)-2-iminoimidazolidin-4-yl]seryl-seryl]

EXAMPLE 97a

Cyclo[glycyl-β-methylphenylalanyl-O-(6-O-heptanoyl-4-O-hexopyranosylhexopyranosyl)-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl3-(3-hexopyra nosyl-2-iminoimidazolidin-4-yl)-serylseryl]

EXAMPLE 97b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(6-O-heptanoylhexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopy ranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

The title compounds are prepared by the procedure described for example 95 using the appropriate carboxylic acid anhydride. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-heptanoylhexopyranos yl)-2-iminoimidazolidin-4-yl]seryl-seryl]: MS (+ES) m/z: 704.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-(6-O-heptanoyl-4-O-hexopyranosylhexopyranosyl)-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyrano syl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES) m/z: 704.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-[4-O-(6-O-heptanoylhexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranos yl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES) m/z: 704.4 (M+2H)2+.

EXAMPLE 98

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-(6-O-(phenylacetyl)hex opyranosyl-2-iminoimidazolidin-4-yl-serylseryl]

EXAMPLE 98a

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoi midazolidin-4-yl-seryl-O-(phenylacetyl)seryl]

EXAMPLE 98b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-(phenylacetyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl-serylseryl]

EXAMPLE 98c

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(phenylacetyl)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

The title compounds are prepared by the procedure described for example 96 using the appropriate carboxylic acid chloride. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-(6-O-(phenylacetyl)hexopy ranosyl-2-iminoimidazolidin-4-yl-serylseryl]: MS (+ES) m/z: 707.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl-seryl-O-(phenylacetyl)seryl]: MS (+ES) m/z: 707.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-(phenylacetyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl-serylseryl]: MS (+ES) m/z: 707.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(phenylacetyl)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexo pyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES) m/z: 707.2 (M+2H)2+.

EXAMPLE 99

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-propylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[3-(6-O-(2-propylpentanoyl)-hexopyranosyl)-2-iminoimidazolidin-4-yl]serylseryl]

EXAMPLE 99a

Cyclo[glycyl-β-methyl]phenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-imino imidazolidin-4-yl)seryl-O-(2-propylpentanoyl)-seryl]

EXAMPLE 99b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-(2-propylpentanoyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 99c

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-propylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 96 using the appropriate carboxylic acid chloride. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-propylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3 -(6-O-(2-propylpentanoyl)-hexopyranosyl)-2-iminoimidazolidin-4-yl]serylseryl]: MS (+ES) m/z: 711.2 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)seryl-O-(2-propylpentanoyl)-seryl]: MS (+ES) m/z: 711.2 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-(2-propylpentanoyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 711.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-propylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 711.3 (M+2H)2+.

EXAMPLE 100

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-(3-cyclopentylpro panoyl)-hexopyranosyl)-2-iminoimidazolidin-4-yl]serylseryl]

EXAMPLE 100a

Cyclo[glycyl-O-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoi midazolidin-4-yl)seryl-O-(3-cyclopentylpropanoyl)seryl]

EXAMPLE 100b

Cyclo[glycyl-β-methylphenylalanyl-O-[6-O-(3-cyclopentylpropanoyl)-4-O-hexopyranosyl-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 100c

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-cyclopentylpropanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 96 using the appropriate carboxylic acid chloride. Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(6-O-(3-cyclopentylpropan oyl)-hexopyranosyl)-2-iminoimidazolidin-4-yl]serylseryl]: MS (+ES) m/z: 710.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)seryl-O-(3-cyclopentylpropanoyl)seryl]: MS (+ES) m/z: 710.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[6-O-(3-cyclopentylpropanoyl)-4-O-hexopyranosyl-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 710.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-cyclopentylpropanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 710.4 (M+2H)2+.

EXAMPLE 101

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-[(phenylmethoxy)carbonyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 101a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(phenylmethoxy)carbonyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-trifluoroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (80 mg) in pyridine (3 mL) is treated with benzyl chloroformate (15 μl). After stirring at room temperature for 20 hr, additional 10 μl of benzyl chloroformate is added. The mixture is stirred for 3 days at room temperature and the volatiles are then removed in vacuo. The residue is triturated with ethyl acetate (3 mL), and the resulting precipitate is collected by filtration, washed with ethyl acetate, dried under vacuum to give a brown solid. The solid is then purified by reverse phase HPLC to provide the title compounds; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-hexopyranosyl-6-O-[(phenylmethoxy)carbonyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 715.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(phenylmethoxy)carbonyl]hexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES), m/z: 715.3 (M+2H)2+.

EXAMPLE 102

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-phenethylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-trifluoroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.5 g) in N,N-dimethylformamide (35 mL) is treated with phenylacetaldehyde dimethyl acetal (0.165 g) and p-toluene sulfonic acid mono-hydrate (0.15 g) and the mixture is stirred at 60-65° C. for 12 h. The reaction mixture is then directly separated by reverse phase HPLC to provide the title compound. MS (+ES), m/z: 699.3 (M+2H)2+.

EXAMPLE 103

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-methoxyphenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.5 g) in N,N-dimethylformamide (5 mL) and dimethyl sulfoxide (5 mL) is treated with 4-methoxyphenylacetaldehyde dimethyl acetal (0.215 g) and p-toluene sulfonic acid mono-hydrate (0.15 g) and the mixture is stirred at 60-65° C. for 12 h. The reaction mixture is then directly separated by reverse phase HPLC to provide the title compound. MS (+ES), m/z: 714.4 (M+2H)2+.

EXAMPLE 104

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

EXAMPLE 104a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

EXAMPLE 104b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (20.9 g, 15.2 mmol) in dimethylsufloxide (100 mL) is treated with benzaldehyde dimethyl acetal (3.7 mL) and hydrogen chloride (1 mL of 4.0M solution in 1,4-dioxane) and the mixture is heated at 50° C. for 24 h. The reaction mixture is cooled to room temperature and acetonitrile (300 mL) is added to precipitate the crude products. The precipitate is collected by filtration, washed with acetonitrile (3×100 mL), and dried. The products are then purified by reverse phase HPLC. Cyclo[glycyl-β-methylphenylalanyl-β-[4-O-(4,6-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES), m/z: 692.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-benzylidenehexopyranosyl)hexopyranosyl)-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES), m/z: 692.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-benzylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexop yranosyl-2-iminoimidazolidin-4-yl)-serylseryl]: MS (+ES), m/z: 692.4 (M+2H)2+.

EXAMPLE 105

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (30.5 g, 22.3 mmol) in dimethyl sulfoxide (110 mL) is treated with adamantanone dimethyl ketal (8.0 g) and hydrogen chloride (1.6 mL of 4.0 M in 1,4-dioxane). The mixture is heated at 50° C. for 1 h before 10 mL of DMSO is removed in vacuo. The resulting solution is directly subjected to purification by reverse phase HPLC. MS (+ES), m/z: 714.4 (M+2H)2+.

EXAMPLE 106

Cyclo[3-cyclohexylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexo pyranosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl]

EXAMPLE 106a

Cyclo[3-cyclohexylalanyl-O-[4-O-[2,3-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexo pyranosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl]

EXAMPLE 106b

Cyclo[3-cyclohexylalanyl-O-[4-O-[2,3:4,6-di-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl]

A stirred solution of the bis-acetate salt of cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl] (8.2 g) in dimethyl sulfoxide (110 mL) is treated with adamantanone dimethyl ketal (3.0 g) and hydrogen chloride (5 mL of 4.0 M in 1,4-dioxane). The mixture is heated at 50° C. for 2 h and then cooled and neutralized (pH paper) by the addition of N,N-diisopropylethylamine (1 mL). Acetonitrile (400 mL) is added to precipitate the crude products, which are collected by filtration and washed with acetonitrile, diethyl ether, and air dried. The resulting solids are subjected to purification by reverse phase HPLC. Cyclo[3-cyclohexylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyr anosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl]: MS (+ES), m/z: 710.6 (M+2H)2+; Cyclo[3-cyclohexylalanyl-O-[4-O-[2,3-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyr anosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl]: MS (+ES), m/z: 710.6 (M+2H)2+; Cyclo[3-cyclohexylalanyl-O-[4-O-[2,3:4,6-di-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)-serylserylglycyl]: MS (+ES), m/z: 776.5 (M+2H)2+.

EXAMPLE 107

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methylbutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 682.2 (M+2H)2+.

EXAMPLE 108

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-hexylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hex opyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 689.4 (M+2H)2+.

EXAMPLE 109

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-octylidenehexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hex opyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 703.3 (M+2H)2+.

EXAMPLE 110

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,3-dimethylbutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 689.1 (M+2H)2+.

EXAMPLE 111

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-methylpentylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 689.3 (M+2H)2+.

EXAMPLE 112

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclohexylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 695.3 (M+2H)2+.

EXAMPLE 113

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[2-[1-[(phenylmethoxy)carbonyl]piperidin-4-yl]ethylidene]hexopyranosyl]hexopyranosyl]tyro syl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 769.8 (M+2H)2+.

EXAMPLE 114

Cyclo[glycyl-β-methyl]phenylalanyl-O-[4-O-[4,6-O-(4-butoxy-4-oxobutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate di-n-butyl acetal. MS (+ES) m/z: 718.4 (M+2H)2+.

EXAMPLE 115

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclohex-3-en-1-ylmethylene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 694.4 (M+2H)2+.

EXAMPLE 116

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-ethylbutylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 689.4 (M+2H)2+.

EXAMPLE 117

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclopentylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 102 using the appropriate dimethyl acetal. MS (+ES) m/z: 688.3 (M+2H)2+.

EXAMPLE 118

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-bromophenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 103 using the appropriate dimethyl acetal. MS (+ES) m/z: 738.8 (M+2H)2+.

EXAMPLE 119

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-methylphenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 103 using the appropriate dimethyl acetal. MS (+ES) m/z: 706.3 (M+2H)2+.

EXAMPLE 120

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-chlorophenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 103 using the appropriate dimethyl acetal. MS (+ES) m/z: 716.4 (M+2H)2+.

EXAMPLE 121

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-fluorophenethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 103 using the appropriate dimethyl acetal. MS (+ES) m/z: 708.3 (M+2H)2+.

EXAMPLE 122

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-cyclohexylethylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 702 (M+2H)2+.

EXAMPLE 123

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(5-methylhex-4-en-1-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 695.3 (M+2H)2+.

EXAMPLE 124

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-phenylpropylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 706.3 (M+2H)2+.

EXAMPLE 125

Cyclo[glycyl-β-methyl]phenylalanyl-O-[4-O-[4,6-O-(2,6-dimethylhept-5-en-1-yidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolid in-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 709 (M+2H)2+.

EXAMPLE 126

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,7-dimethyloct-6-en-1-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidi n-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 716.1 (M+2H)2+.

EXAMPLE 127

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(1-adamantylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 721.4 (M+2H)2+.

EXAMPLE 128

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-[2-(1-adamantyl)ethylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 728.4 (M+2H)2+.

EXAMPLE 129

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[2-(1-adamantyl)ethylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 728.8 (M+2H)2+.

EXAMPLE 130

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methoxycholan-24-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 826.4 (M+2H)2+.

EXAMPLE 131

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-(4-phenylbenzylidene)-hexopyranosyl)hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 690.2 (M+2H)2+.

EXAMPLE 132

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-thienylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 696 (M+2H)2+.

EXAMPLE 133

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-thienylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 695 (M+2H)2+.

EXAMPLE 134

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-methylbenzylidene)hexopyranosyl]-hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 699.2 (M+2H)2+.

EXAMPLE 135

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 699 (M+2H)2+.

EXAMPLE 136

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-hydroxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 700 (M+2H)2+.

EXAMPLE 137

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 137a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 137b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 104 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 707.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 707.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3-methoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 707.3 (M+2H)2+.

EXAMPLE 138

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-chlorobenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 709.2 (M+2H)2+.

EXAMPLE 139

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-isopropylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 713.4 (M+2H)2+.

EXAMPLE 140

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-propylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 713.3 (M+2H)2+.

EXAMPLE 141

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-carboxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 714.6 (M+2H)2+.

EXAMPLE 142

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-ethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 714.3 (M+2H)2+.

EXAMPLE 143

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(1,3-benzodioxol-5-ylmethylene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 714.3 (M+2H)2+.

EXAMPLE 144

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(methylthio)benzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 715 (M+2H)2+.

EXAMPLE 145

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-naphthylmethylene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 717.3 (M+2H)2+.

EXAMPLE 146

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(2-methylprop-1-en-1-yl)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimi dazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 719.2 (M+2H)2+.

EXAMPLE 147

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-tert-butylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 720.4 (M+2H)2+.

EXAMPLE 148

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-propyloxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 721.3 (M+2H)2+.

EXAMPLE 149

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[(2,3-dihydro-1,4-benzodioxan-6-yl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-im inoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 721 (M+2H)2+.

EXAMPLE 150

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,5-dimethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 150a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3,5-dimethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 104 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,5-dimethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 722.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-(3,5-dimethoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 722.3 (M+2H)2+.

EXAMPLE 151

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methyl-4-nitrobenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 722.5 (M+2H)2+.

EXAMPLE 152

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-ethoxy-4-methoxybenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 729.2 (M+2H)2+.

EXAMPLE 153

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-methoxy-4-nitrobenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 729.5 (M+2H)2+.

EXAMPLE 154

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-phenylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)ser yl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 730.2 (M+2H)2+.

EXAMPLE 155

Cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-[(2,2-dimethylpropanoyl)imino]imidazolidin-4-yl]seryl-3- (3-hexolpyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 730.3 (M+2H)2+.

EXAMPLE 156

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(3-pridyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 730.8 (M+2H)2+.

EXAMPLE 157

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(methylsulfonyl)benzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexolpyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 731 (M+2H)2+.

EXAMPLE 158

Cyclo[glycyl-β-methylphenylalanyl-β-[4-O-[4,6-O-[(6-chloro-1,3-benzodioxol-5-yl)-methylene]hexolpyranosyl]hexopranosyl]tyrosyl-3-(2-imino imidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 731.2 (M+2H)2+.

EXAMPLE 159

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[(6-methoxy-2-naphthyl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 732.3 (M+2H)2+.

EXAMPLE 160

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-[(6-methoxy-2-naphthyl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 732.5 (M+2H)2+.

EXAMPLE 161

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[1-(acetylindol-3-yl)methylene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 732.8 (M+2H)2+.

EXAMPLE 162

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(3-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 733.3 (M+2H)2+.

EXAMPLE 163

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(2-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 733.3 (M+2H)2+.

EXAMPLE 164

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(3-thienyl)benzylidene]hexopyranosyl]-hexolpyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 164a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-[4-(3-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 104 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(3-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2,3-O-[4-(3-thienyl)benzylidene]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.3 (M+2H)2+.

EXAMPLE 165

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-[(3-methylbut-2-en-1-yl)oxy]-benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-imin oimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 734 (M+2H)2+.

EXAMPLE 166

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(carboxymethoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 736.2 (M+2H)2+.

EXAMPLE 167

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-ethoxy-4-nitrobenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 736.8 (M+2H)2+.

EXAMPLE 168

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(methylthio)-3-nitrobenzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazol idin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 737.73 (M+2H)2+.

EXAMPLE 169

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-hydroxy-3-methoxy-4-nitro-benzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoim idazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 737.5 (M+2H)2+.

EXAMPLE 170

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3-phenoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 738 (M+2H)2+.

EXAMPLE 171

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-phenoxybenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 738.3 (M+2H)2+.

EXAMPLE 172

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(2-phenylethenyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidi n-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 743.4 (M+2H)2+.

EXAMPLE 173

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-benzoylbenzylidene)hexopyranosyl]-hexopyranosyl]tyrosyl -3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 744.2 (M+2H)2+.

EXAMPLE 174

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-methylphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidi n-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 745 (M+2H)2+.

EXAMPLE 175

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(phenylmethoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 745 (M+2H)2+.

EXAMPLE 176

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(phenylmethoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 745.3 (M+2H)2+.

EXAMPLE 177

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(4-chlorophenyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 747.3 (M+2H)2+.

EXAMPLE 178

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-chlorophenyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 747.3 (M+2H)2+.

EXAMPLE 179

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(1,1,2,2-tetrafluoroethoxy)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-imino imidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 750 (M+2H)2+.

EXAMPLE 180

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(4-methoxyphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolid in-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 753 (M+2H)2+.

EXAMPLE 181

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-tert-butylphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazo lidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 766 (M+2H)2+.

EXAMPLE 182

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-[(4-nitrophenyl)methoxy]benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimid azolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 768.1 (M+2H)2+.

EXAMPLE 183

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(3,7-dimethylocta-2,6-dien-1-yl)oxy]-benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3 -(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 768 (M+2H)2+.

EXAMPLE 184

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-[3-(trifluoromethyl)phenoxy]-benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-imin oimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 772 (M+2H)2+.

EXAMPLE 185

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[[3-(3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy]benzylidene]hexopyranosyl]hexopyranosyl ]tyrosyl-3-(2-iminoimidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 802 (M+2H)2+.

EXAMPLE 186

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(4-iodobenzoyl)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 807.2 (M+2H)2+.

EXAMPLE 187

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[4-(3,4,5-triiodobenzoyl)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimida zolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 933.4 (M+2H)2+.

EXAMPLE 188

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,3-diphenylprop-2-enylidene)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 743.2 (M+2H)2+.

EXAMPLE 189

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(prop-2-enylidene)hexopyranosyl]-hexopyranosyl]tyrosyl -3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 667.4 (M+2H)2+.

EXAMPLE 190

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6- O-[(6-methoxy-2-naphthyl)-methylene]hexopyranosyl]hexopyranosyl]tyrosyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 716.3 (M+2H)2+.

EXAMPLE 191

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6- O-[4-(phenylmethoxy)benzylidene]-hexolpyranosyl]hexopyranosyl]tyrosyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 729.6 (M+2H)2+.

EXAMPLE 192

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6- O-[3-(4-methoxyphenoxy)benzylidene]-hexopyranosyl]hexopyranosyl]tyrosyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 737.4 (M+2H)2+.

EXAMPLE 193

Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[4,6-O-(cyclohexylmethylene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 712.3 (M+2H)2+.

EXAMPLE 194

Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-methylpentylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 706.2 (M+2H)2+.

EXAMPLE 195

Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 709.5 (M+2H)2+.

EXAMPLE 196

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)hexopyranosyl]-3-iodotyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)-3-iodo-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-i minoimidazolidin-4-yl)serylseryl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 755 (M+2H)2+.

EXAMPLE 197

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-[3-(4-methylphenoxy)benzylidene]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidi n-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyhanosyl)-3-iodo-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-i minoimidazolidin-4-yl)serylseryl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 808 (M+2H)2+.

EXAMPLE 198

Cyclo[3-cyclohexylalanyl-O-[4-O-[4,6-O-(3-phenylpropylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycl]

The title compound is prepared from cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 702.3 (M+2H)2+.

EXAMPLE 199

Cyclo[3-cyclohexylalanyl-O-[4-O-(4,6-O-benzylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosy l-2-iminoimidazolidin-4-yl)-seryl-serylglycyl]

The title compound is prepared from cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl]by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 688.1 (M+2H)2+.

EXAMPLE 200

Cyclo[3-cyclohexylalanyl-O-[4-O-[4,6-O-phenethylidene-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyra nosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]

The title compound is prepared from cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin- 4-yl)serylserylglycyl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 695.2 (M+2H)2+.

EXAMPLE 201

Cyclo[3-cyclohexyl-2-aminobutanoyl-O-[4-O-[4,6-O-benzylidenehexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-he xopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]

The title compound is prepared from cyclo[3-cyclohexyl-2-aminobutanoyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimi dazolidin-4-yl)-serylserylglycyl] by the procedure described for example 104 using the appropriate dimethyl acetal. MS (+ES) m/z: 695.1 (M+2H)2+.

EXAMPLE 202

Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclopentylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 681.2 (M+2H)2+.

EXAMPLE 203

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclohexylidene-4-hexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 688.2 (M+2H)2+.

EXAMPLE 204

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-methylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 695.3 (M+2H)2+.

EXAMPLE 205

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2,2-dimethylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 702.3 (M+2H)2+.

EXAMPLE 206

Cyclo[glycyl-β-methylphenylalanyl-β-[4-β-[4,6-β-(2,6-dimethylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 702.4 (M+2H)2+.

EXAMPLE 207

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(3,3,5,5-tetramethylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazo lidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 716.3 (M+2H)2+.

EXAMPLE 208

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-tert-butylcyclohexylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 716 (M+2H)2+.

EXAMPLE 209

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclododecylidenehexopyranosyl)-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 730.4 (M+2H)2+.

EXAMPLE 210

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-cyclotridecylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 737.2 (M+2H)2+.

EXAMPLE 210a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(2,3-O-cyclotridecylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 737.2 (M+2H)2+.

EXAMPLE 211

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(bicylo-[3,2.1]oct-2-ylidene)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 701.1 (M+2H)2+.

EXAMPLE 212

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-bicyclo[3.3.1]non-9-ylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 708.7 (M+2H)2+.

EXAMPLE 213

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-(4,6-O-tricyclo[5.2.1.0(2,6)]decan-2-ylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidaz olidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 714.3 (M+2H)2+.

EXAMPLE 214

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-imi noimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 715.2 (M+2H)2+.

EXAMPLE 215

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-imi noimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 715.3 (M+2H)2+.

EXAMPLE 216

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(4-fluoro-α-methylbenzylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 708.4 (M+2H)2+.

EXAMPLE 217

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(tetrahydrothiopyran-4-ylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 697.4 (M+2H)2+.

EXAMPLE 218

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)-3-O-(3-methyl-butanoyl)-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-imino imidazolidin-4-yl)-seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-h exopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 756.4 (M+2H)2+.

EXAMPLE 219

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4,6- O-(2-adamantylidene)hexopyranosyl]-hexopyranosyl]tyrosyl]

The title compound is prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 698.9 (M+2H)2+.

EXAMPLE 220

Cyclo[glycylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]-tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexo pyranosyl-2-iminoimidazolidin-4-yl]-serylseryl]

The title compound is prepared from cyclo[glycylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminomidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4 -yl)serylseryl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 707.4 (M+2H)2+.

EXAMPLE 221

Cyclo[3-cyclohexyl-2-aminobutanoyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]

The title compound is prepared from cyclo[3-cyclohexyl-2-aminobutanoyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimi dazolidin-4-yl)-serylserylglycyl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 717.2 (M+2H)2+.

EXAMPLE 222

Cyclo[3-cyclohexylalanyl-3-[4-[[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]

The title compound is prepared from cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylserylglycyl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 713.3 (M+2H)2+.

EXAMPLE 223

Cyclo[3-cyclohexylalanyl-3-[4-[[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]

The title compound is prepared from cyclo[3-cyclohexylalanyl-3-[4-[(4-O-hexopyranosylhexopyranosyl)oxy]cyclohexyl]alanyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2- iminoimidazolidin-4-yl)serylserylglycyl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 713.2 (M+2H)2+.

EXAMPLE 224

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(1-butyl-3-hexolpyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[1-butyl-3-hexopyranosyl-2-i minoimidazolidin-4-yl]serylseryl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 742.6 (M+2H)2+.

EXAMPLE 225

Cyclo[glycyl-1-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[3-hexopyranosyl-2-imino-1-(3-methylbut-2-en-1-yl)imidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-hexopyranosyl-2-imino-1-( 3-methyl-but-2-enyl)imidazolidin-4-yl]serylseryl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 748.5 (M+2H)2+.

EXAMPLE 226

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -[3-hexopyranosyl-2-imino-1-[4-(trifluoromethyl)-benzyl]imidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl]-3-[3-hexopyranosyl-2-imino-1- (4-trifluoromethylbenzyl)-imidazolidin-4-yl]-serylseryl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 793.5 (M+2H)2+.

EXAMPLE 227

Di-N-(2-(1,3-benzoxazolyl)-cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[2-imi noimidazolidin-4-yl]seryl-3-[3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(pyrimidin-2-ylimino)imidazolidin-4-yl]seryl-3-[3-hexopyran osyl-2-imino-1-(pyrimidin-2-yl)imidazolidin-4-yl]serylseryl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 831.1 (M+2H)2+.

EXAMPLE 228

Di-N-(2-(pyrimidinyl)-cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4,6-O-(2-adamantylidene)hexopyranosyl]hexopyranosyl]tyrosyl-3-[2-iminoimi dazolidin-4-yl]seryl-3-[3-hexolpyranosyl-2-iminoimidazolidin-4-yl]serylseryl]

The title compound is prepared from cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-[2-(1,3-benzoxazol-2-ylimino)imidazolidin-4-yl]seryl-3-[1-(1,3 -benzoxaxol-2-yl)-3-hexopyranosyl-2-iminoimidazolidin-4-yl]serylseryl] by the procedure described for example 104 using the appropriate dimethyl ketal. MS (+ES) m/z: 792.2 (M+2H)2+.

EXAMPLE 229

Cyclo[glycyl-β-methylphenylalanyl-O-(2,3-O-isopropylidene-4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[2-i mino-(2,3-O-isopropylidene-hexopyranosyl)imidazolidin-4-yl]serylseryl]

EXAMPLE 229a

Cyclo[glycyl-β-methylphenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3-isopropylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolid in-4-yl)seryl-3-[2-imino-3-(2,3-O-isopropylidenehexopyranosyl)imidazolidin-4-yl]serylseryl]

EXAMPLE 229b

Cyclo[glycyl-β-methylphenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3:4,6-di-O-isoprolpylidene-hexopyranosyl)hexopyranosyl]tyrosyl-3-(2-imin oimidazolidin-4-yl)seryl-3-[2-imino-(2,3-O-isopropylidenehexopyranosyl)imidazolidin-4-yl]serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (0.908 g) in N,N-dimethylformamide (16 mL) is treated with 2,2-dimethoxypropane (5 mL) and hydrogen chloride (0.15 mL of a 4.0 M solution in 1,4-dioxane) and the mixture is stirred for 3 days at room temperature. The resultant solution is concentrated in vacuo to approximately one-third of the original volume, added to acetonitrile (32 mL) and the resultant precipitate collected by centrifugation. The precipitate is resuspended in acetonitrile (32 mL) and recentrifuged. The products are then purified by reverse phase HPLC. Cyclo[glycyl-β-methylphenylalanyl-O-(2,3-O-isopropylidene-4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[2-imin o-(2,3-O-isopropylidene-hexopyranosyl)imidazolidin-4-yl]serylseryl]: MS (+ES) m/z: 688.6 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3-isopropylidenehexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin- 4-yl)seryl-3-[2-imino-3-(2,3-O-isopropylidenehexopyranosyl)imidazolidin-4-yl]serylseryl]: MS (+ES) m/z: 708.5 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[2,3-O-isopropylidene-4-O-(2,3:4,6-di-O-isopropylidene-hexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimi dazolidin-4-yl)seryl-3-[2-imino-(2,3-O-isopropylidenehexopyranosyl)imidazolidin-4-yl]serylseryl]: MS (+ES) m/z.: 728.6 (M+2H)2+.

EXAMPLE 230

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 230a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 230b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 230c

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (5.46 g) in dimethyl sulfoxide (25 mL) is treated with 6-methoxy-2-naphthaldehyde dimethyl acetal (1.856 g) and hydrogen chloride (1 mL of 1.0M solution in diethyl ether), and the mixture is heated at 50° C. for 1 h. The reaction mixture is then cooled to room temperature and poured into water (100 mL) containing dilute sodium hydroxide solution. The pH of the solution is then adjusted to pH 10, and the resulting precipitates are filtered and washed with a mixture of acetonitrile and diethyl ether (1:1). The crude acetal thus obtained is air dried and used in the next step without further purification. An ice cold solution of trifluoroacetic acid (3.192 g) in N,N-dimethylformamide (5 mL) is added dropwise to a cooled (0° C.) mixture containing the above acetal derivative (2.04 g) and sodium cyanoborohydride (0.879 g) in N,N-dimethylformamide (20 mL). The mixture is then stirred for 24 h and gradually warmed to room temperature, and is then poured into water (50 mL). A dilute solution of sodium hydroxide is added to adjust to pH 10, the resulting solid is filtered, washed several times with water, then acetonitrile and dried. This solid is then purified by reverse phase HPLC to provide the title compounds. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.2 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl]-O-[4-O-[4-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl]-O-[4-O-[3-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[(6-methoxy-2-naphthyl)methyl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (ES) m/z: 733.2 (M+2H)2+.

EXAMPLE 231

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 231a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 231b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 231c

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 230 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 746.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 746.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 746.7 (M+2H)2+: Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-[4-(phenylmethoxy)benzyl]hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 746.7 (M+2H)2+.

EXAMPLE 232

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-methoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 708.3 (M+2H)2+.

EXAMPLE 233

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-ethoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3- hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 715.4 (M+2H)2+.

EXAMPLE 234

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-methylbenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3- hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 700.2 (M+2H)2+.

EXAMPLE 235

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-propoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 722.3 (M+2H)2+.

EXAMPLE 236

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(4-phenoxybenzyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 739.2 (M+2H)2+.

EXAMPLE 237

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-fluoro-4-methoxybenzyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 717.3 (M+2H)2+.

EXAMPLE 238

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-ethoxy-4-methoxybenzyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 730.3 (M+2H)2+.

EXAMPLE 239

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4-methoxy-3-(phenylmethoxy)benzyl]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 239a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4-methoxy-3-(phenylmethoxy)benzyl]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 230 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4-methoxy-3-(phenylmethoxy)benzyl]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 761.3 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4-methoxy-3-(phenylmethoxy)benzyl]-hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin -4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 761.8 (M+2H)2+.

EXAMPLE 240

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 240a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosy]lhexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 240b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosy]lhexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4 -yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 230 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosy]lhexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.6 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosy]lhexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.5 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-[(4-methoxy-1-naphthyl)methyl]hexo-pyranosy]lhexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 733.4 (M+2H)2+.

EXAMPLE 241

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3,3-diphenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 241a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(3,3-diphenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 230 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3,3-diphenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 744.4 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(3,3-diphenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 744.7 (M+2H)2+.

EXAMPLE 242

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(3-phenylprop-2-en-1-yl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)se ryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 706.3 (M+2H)2+.

EXAMPLE 243

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[3-[4-(dimethylamino)phenyl]prop-2-en-1-yl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoim idazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 243a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[3-[4-(dimethylamino)phenyl]prop)-2-en-1-yl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoi midazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 230 using the appropriate dimethyl acetal. Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-[3-[4-(dimethylamino)phenyl]prop-2-en-1-yl]hexopyranosyl)hexopyranosyl]tyrosyl-3-(2-iminoimida zolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 728.0 (M+2H)2+; Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-[3-[4-(dimethylamino)phenyl]prop-2-en-1-yl]hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimida zolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 728.0 (M+2H)2+.

EXAMPLE 244

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-(2-thienylmethyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3 -hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compound is prepared by the procedure described for example 230 using the appropriate dimethyl acetal. MS (+ES) m/z: 696.3 (M+2H)2+.

EXAMPLE 245

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[6-O- [(6-methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]

EXAMPLE 245a

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4-O- [(6-methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]

EXAMPLE 245b

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[3-O- [(6-methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]

EXAMPLE 245c

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[2-O- [(6-methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]

The title compounds are prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 230 using the appropriate dimethyl acetal. Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[6-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.6 (M+2H)2+; Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.7 (M+2H)2+; Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[3-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.7 (M+2H)2+; Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[2-O-[(6 -methoxy-2-naphthyl)methyl]-hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.7 (M+2H)2+.

EXAMPLE 246

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[6-O- [4-(phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]

EXAMPLE 246a

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4-O- [4-(phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]

EXAMPLE 246b

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[3-O- [4-(phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]

EXAMPLE 246c

Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[2-O- [4-(phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]

The title compounds are prepared from cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-(4-O-hexopyra nosylhexopyranosyl)tyrosyl] by the procedure described for example 230 using the appropriate dimethyl acetal. Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[6-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.6 (M+2H)2+; Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[4-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.7 (M+2H)2+; Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[3-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.7 (M+2H)2+: Cyclo[3-(2-iminoimidazolidin-4-yl)alanyl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)-alanylserylglycyl-β-methylphenylalanyl-O-[4-O-[2-O-[4- (phenylmethoxy)benzyl]hexopyranosyl]hexopyranosyl]tyrosyl]: MS (+ES) m/z: 717.7 (M+2H)2+.

EXAMPLE 247

Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2,3:4,6-diisopropylidenehexopyranosyl)-2-iminoimidazolidin- 4-ylserylseryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl] (2.85 g) in N,N-dimethylformamide (20 mL) is treated with 2,2-dimethoxypropane (5.8 mL) and p-toluenesulfonic acid mono-hydrate (35 mg) and the mixture is stirred for 16 h at room temperature. Water (1 mL) is then added, the mixture is stirred for 30 min at room temperature, and then acetonitrile (100 mL) is added dropwise to precipitate the product. After stirring for 45 min at 0° C., the product is collected by filtration, and is then washed with acetonitrile, diethyl ether, and air dried. MS (+ES) m/z: 526.6 (M+2H)2+.

EXAMPLE 248

Cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(2,3:4,6-di-O-isopropylidenehexopyranosyl)-2-iminoimidazo lidin-4-yl]seryl-O-(tert-butyldimethylsilyl)seryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2,3:4,6-diisopropylidenehexopyranosyl)-2-iminoimidazolidin-4-y lserylseryl] (2.25 g) in N,N-dimethylformamide (15 mL) containing 2,6-lutidine (4 mL) is treated dropwise at −45° C. with a solution of t-butyldimethylsilyl triflate in N,N-dimethylformamide (2 M, 5 mL) and the mixture is stirred for 2 h at −45° C. Methanol (1.5 mL) is added, and then diethyl ether (200 mL) is added to the reaction mixture. Stirring is stopped and the resulting oil is permitted to settle. The solvents are decanted and an additional portion of diethyl ether (200 mL) is added. After stirring briefly, and then allowing the oil to settle, the solvents are again decanted. Acetonitrile (175 mL) is added to precipitate the product, which is collected by filtration and then washed with acetonitrile, diethyl ether, and air dried. MS (+ES) m/z: 583.6 (M+2H)2+.

EXAMPLE 249

Tri-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(2,3:4,6-di-O-isopropylid enehexopyranosyl)-2-iminoimidazolidin-4-yl]seryl-O-(tert-butyldimethylsilyl)seryl]

A stirred solution of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-[3-(2,3:4,6-di-O-isopropylidenehexopyranosyl)-2-iminoimidazolid in-4-yl]seryl-O-(tert-butyldimethylsilyl)seryl] (1.97 g) in N,N-dimethylformamide (15 mL) containing N,N-diisopropylethylamine (1 mL) is treated with N-(benzyloxycarbonyloxy)-succinimide (1.48 g) and the mixture is stirred for 16 h at room temperature. The mixture is then diluted with ethyl acetate and washed twice with saturated aqueous sodium bicarbonate, twice with water, and then with saturated aqueous sodium chloride. The organic phase is then dried over anhydrous sodium sulfate, filtered and concentrated to provide an oil. This oil is dissolved in a minimal amount of dichloromethane and treated with hexanes to precipitate the product. The product is then collected by filtration, washed with hexanes, and dried. MS (+ES) m/z: 784.6 (M+2H)2+.

EXAMPLE 250

Tetra-N-[(phenylmethoxy)carbonyl]-cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl) seryl-O-(tert-butyldimethylsilyl)seryl]

A stirred solution of the bis-hydrochloride salt of cyclo[glycyl-β-methylphenylalanyltyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(2-iminoimidazolidin-4-yl)serylseryl] (590 mg) in N,N-dimethylformamide (6 mL) containing 2,6-lutidine (0.5 mL) is treated dropwise at −45° C. with t-butyldimethylsilyl triflate (0.62 mL) and the mixture is stirred for 16 h and then gradually warmed to room temperature. Methanol (0.25 mL) is added, the mixture is stirred for 10 min, and then N,N-diisopropylethylamine (0.66 mL) and N-(benzyloxycarbonyloxy)-succinimide (0.84 g) are sequentially added. The mixture is stirred for 2 h, and then additional N,N-diisopropylethylamine (0.33 mL) and N-(benzyloxycarbonyloxy)-succinimide (0.33 g) are added. After 2 more hs, the mixture is diluted with ethyl acetate and washed twice with saturated aqueous sodium bicarbonate, twice with water, and then with saturated aqueous sodium chloride. The organic phase is then dried over anhydrous sodium sulfate, filtered and concentrated to provide an oil. This oil is chromatographed over silica gel to provide the title compound. MS (+ES) m/z: 730.9 (M+2H)2+.

EXAMPLE 251

α-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 251a

β-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 251b

γ-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A solution of the bis-trifluoroacetate salt of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl] (250 mg) in N,N-dimethylformamide (1.6 mL) at 0° C. is treated dropwise with a 1M solution of N,N′-carbonyldiimidazole in N,N-dimethylformamide (0.25 mL) and the reaction is stirred for 2 h at 0° C. Isoamyl amine (0.16 mL) is added and the reaction is stirred overnight at approximately 4° C. Acetonitrile (˜2 mL) is then added to precipitate the products. Solids are collected by filtration, washed with acetonitrile and ether, air dried, and then purified by reverse phase HPLC. α-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]:MS (+ES) m/z: 704.8 (M+2H)2+; β-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 704.8 (M+2H)2+; γ-O-[(Pentylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 704.6 (M+2H)2+.

EXAMPLE 252

α-O-[(Butylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 252a

β-O-[(Butylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl- 3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 251 using the appropriate alkyl amine. α-O-[(Butylamino)carbonyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 697.8 (M+2H)2+; β-O-[(Butylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-( 3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 697.9 (M+2H)2+.

EXAMPLE 253

α-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 253a

β-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 253b

γ-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methyl]phenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 251 using the appropriate alkyl amine. α-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 718.8 (M+2H)2+; β-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 718.9 (M+2H)2+; γ-O-[(Heptylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 718.9 (M+2H)2+.

EXAMPLE 254

α-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 254a

β-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 254b

γ-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 251 using the appropriate alkyl amine. α-O-[(Dodecylamino)carbonyl)-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 753.8 (M+2H)2+; β-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 754.0 (M+2H)2+; γ-O-[(Dodecylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 753.9 (M+2H)2+.

EXAMPLE 255

α-O—[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidaz olidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 255a

β-O—[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidaz olidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 251 using the appropriate alkyl amine. α-O—[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 705.0 (M+2H)2+; β-O—[(N-Methyl-2-methylpropylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazoli din-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 704.8 (M+2H)2+.

EXAMPLE 256

α-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 256a

β-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 251 using the appropriate alkyl amine. α-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 710.7 (M+2H)2+; β-O-[(Cyclohexylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)sery l-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 710.9 (M+2H)2+.

EXAMPLE 257

α-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 257a

β-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 257b

γ-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

The title compounds are prepared by the procedure described for example 251 using the appropriate alkyl amine. α-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 714.8 (M+2H)2+; β-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 714.8 (M+2H)2+; γ-O-[(Benzylamino)carbonyl]-cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]: MS (+ES) m/z: 714.8 (M+2H)2+.

EXAMPLE 258

SEED PREPARATION

A seed medium of the following formulation is prepared:

Bacto tryptic soy broth1 (dehydrated)3%
Dextrose2%
Distilled water

1(Soybean-casein digest medium, Difco Laboratories, Detroit MI)

The seed medium is prepared by adding a filter-sterilized dextrose solution to the tryptic soy broth after autoclaving. Fifty mL of seed medium in a 250 mL Erlenmeyer flask is inoculated with cells from a mutant strain (see table below) cultured on ATCC agar medium #172 (ATCC Media Handbook, 1st edition, 1984).

Sufficient inoculum from the agar culture is used to provide a turbid seed after 24-36 h. of growth. The seed is incubated at 30° C., 200 rpm using a gyro-rotary shaker with a 2 inch throw, for 24-36 h. To prepare inoculum for fermentors, 1 liter of the above seed medium in a 2.8 liter Fernbach flask is inoculated with 5 mL of cryo-preserved seed culture and is incubated as above.

EXAMPLE 259

DIRECTED BIOSYNTHESIS OF GLYCOPEPTIDE ANTIBIOTICS

A fermentation medium of the following formulation is prepared:

Pharmamedia2  2%
Calcium carbonate0.5%
Dextrose  4%
Distilled water

2(Cottonseed flour, Traders Oil Mill Co., Fort Worth, TX Trader's Guide to Fermentation Media Formulation, 1980)

This medium is prepared by adding a filter-sterilized dextrose solution to autoclaved Pharmamedia™/calcium carbonate broth. A production medium volume of 50 mL in a 250 mL Erlenmeyer flask is supplemented to a final concentration of 2 mM of a selected amino acid or 16 mM of a selected fatty acid. This flask is then inoculated with 1 mL of seed culture prepared as described in Example 258. Production fermentations are incubated at 30° C., 250 rpm, 2 in. throw for up to 7 days. For large-scale production of glycopeptide antibiotics of the invention, 15 L glass jar fermentors are prepared with 10 L of the above production medium supplemented with the selected amino acid or fatty acid. Fermentors are inoculated with 200 mL of seed culture and are incubated at 30° C., 800 rpm with an air flow rate of 10 L per minute.

EXAMPLE 260a

ISOLATION AND IDENTIFICATION OF GLYCOPEPTIDE ANTIBIOTICS

The supernatant of a fermentation broth, obtained by centrifugation at 3000×g, is loaded on a column containing pre-washed polyarylate absorbant resin XAD-7 at approximately a 1:10 resin/supernatant ratio (v/v) for a typical extraction. The column is then sequentially washed with water, methanol, and Water (each with ˜2 column volumes). The crude glycopeptide antibiotics are eluted by 1:1 acetonitrile in water containing 0.05-0.1% trifluoroacetic acid (2-3 column volumes). Upon evaporation under reduced pressure, the residue is redissolved in water or water/methanol mixture and subjected to reverse phase high performance liquid chromatography (HPLC) to afford the pure antibiotics. Typically the IPLC is performed with C18 reverse phase columns (YMC ODS-A, 120A pore size) using mixtures of acetonitrile or methanol in water containing small amounts of trifluoroacetic acid to control the acidity in the range of pH 3.5 and 5.5

The purified antibiotics are then subjected to structural determination by spectroscopic analysis. The molecular weights are usually determined by electrospray ionization mass spectrometry (ESI MS) measured with a Finnigan LCQ instrument in positive mode. The structures are determined by interpretation of 1-D and 2-D nuclear magnetic resonance (NMR) spectral data in 1:1 D2O/CD3OD, including 1H—1H COSY, TOCSY and 1H—13C HMBC, and HMQC data. New antibiotics discerned by the above described conditions are shown in the Examples 261a, 261b, 261c, 262a, 262b, 263, 264a, 264b, 265a, 265b, 270a, 270b, 271a, 275, 277a, 277b, 277c, 278a, 278b, 278c, 278d, 279a, 279b, 280a, 280b, 282, 283a, 283b, 283c, 284b and 296.

EXAMPLE 260b

DETECTION OF GLYCOPEPTIDE ANTIBIOTICS BY BY HPLC AND LC/MS

Fermentation broth is centrifuged (3000×g), and the supernatant is applied to a wetted BAKERBOND™ spe carboxylic acid extraction column (catalog #7211-03). Columns are washed with 50% aqueous methanol and are eluted with acetonitrile/water/trifluoroacetic acid (70/30/0.5). The solvent is evaporated, and the residue is reconstituted in 0.2 mL methanol/water (2/8). Samples are analyzed by HPLC, and the production of new glycopeptide antibiotics of the invention is monitored. Reverse phase HPLC is performed using a Hewlett Packard model 1090M liquid chromatograph with photodiode array detection, a YMC ODS-A 4.6×150 mm HPLC column, and a mobile phase of 0.02% trifluoroacetic acid in water (solvent A) and acetonitrile (solvent B). A linear gradient from 5% B to 34% B in 15 min, with a flow rate of 1 mL/min is used for elution. Relative retention times (RRT) are calculated by dividing the peak retention times of the new glycopeptide antibiotics prepared herein by that of cyclo[glycyl-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimid azolidin-4-yl)serylseryl]. The incorporation of amino acids or fatty acids into the glycopeptide antibiotics is indicated by liquid chromatography/mass spectrometry (LC/MS) analysis of fermentation extracts and a comparison of the molecular weights of new peaks with the predicted molecular weight of glycopeptide antibiotics containing the amino acid or fatty acid analogs.

The molecular weights of new glycopeptide antibiotics of the invention are determined using a Hewlett-Packard APCI-electrospray LC/MS system with an HP 5989B Mass Spectrometer, HP 59987A APCI-Electrospray, HP 1090 series II HPLC and HP ChemStation data system with HP G1047A LC/MS software. Extracts are resolved by reverse phase HPLC as described above. UV detection is at 226 nm. The ESI MS is performed in positive mode. New glycopeptide antibiotics discerned by the above described conditions are shown in the Examples 262c, 264c, 265c, 266a, 266b, 266c, 267a, 267b, 267c, 268, 269a, 269b, 269c, 270c, 271b, 271c, 272a, 272b, 273a, 273b, 274a, 274b, 276a and 276b.

EXAMPLE 261a, 261b and 261c

GLYCOPETIDE ANTIBIOTIC INCORPORATING p-FLUORO-DL-PHENYLALANINE

EXAMPLE 261a

Cyclo[glycyl-4-fluoro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 261b

Cyclo[glycyl-4-fluoro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-imino-imidazolidin-4-yl)serylseryl]

EXAMPLE 261c

Cyclo[glycyl-4-fluoro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

Approximately 10 L of supernatant of a 7-day fermentation of strain LL4690 supplemented with p-fluoro-DL-phenylalanine, conducted as described in Examples 258 and 259, is loaded on a column containing polyacrylate resin XAD-7 (1 L). The XAD-7 resin is washed sequentially with methanol (2 L), acetone (2 L), and water (4 L) before packing in the column. After loading, the column is sequentially washed with water (2 L), methanol (2 L), and water (2 L) followed by elution with 1:1 acetonitrile in water containing 0.1% trifluoroacetic acid (3 L). The acidic acetonitrile/water fraction is concentrated under reduced pressure to a small volume, and the residue after extraction with 1:4 water/dimethylformamide is fractionated by reverse phase high performance liquid chromatography (HPLC) on a C18 column (YMC ODS-A, 10 micron particle size, 70×500 mm). The mobile phase consists of a gradient from 14 to 50% by volume of acetonitrile in water with 0.02% trifluoroacetic acid over 55 min at a flow rate of 100 mL per min, and the effluent is monitored by UV absorbance at 226 nm. Peak fractions with retention times of approximately 26 min, 33 min, and 36 min are collected to afford Examples 261a, 261b, and 261c, respectively, upon e

EXAMPLE (261a)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 657.2 (m.w.=1312)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE (261b)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 699.2 (m.w.=1396)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE (261c)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 699.3 (m.w.=1396)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLES 262a, AND 262b

GLYCOPEPTIDE ANTIBIOTICS INCORPORATIONG p-CHLORO-DL-PHENYLANINE

EXAMPLE 262a

Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 262b

Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3 (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

Approximately 3 L of supernatant from a 7-day fermentation of strain LL4614 supplemented with p-chloro-DL-phenylalanine, conducted as described in Examples 258 and 259, is processed using XAD-7 column chromatography and HPLC as described in Examples 261a, 261b, and 261c. Peak fractions A and B with respective HPLC retention times at approximately 26 and 36 min are concentrated under reduced pressure and the concentrates are further purified by reverse phase HPLC on a C18 column (YMC ODS-A, 8 micron particle size, 20×250 mm). Further HPLC chromatography of fraction A, using a mobile phase consisting of a gradient from 30 to 60% by volume of methanol in water with 0.02% trifluoroacetic acid over 20 min at a flow rate of 20 mL per min, afforded 262a at approximately 16 min, while chromatography of fraction B, using a gradient solvent system from 45 to 60% of methanol in water with 0.02% trifluoroacetic acid over 20 min, afforded 262b at approximately 18 min upon evaporation.

EXAMPLE (262a)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 665.2 (m.w.=1328)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE (262b)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 707 (m.w.=1412)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE 262c

GLYCOPEPTIDE ANTIBIOTIC INCORPORATING p-CHLORO-DL-PHENYLALANINE

Cyclo[glycyl-4-chloro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A 50 mL fermentation of strain LL4690 supplemented with p-chloro-DL-phenylalanine is performed as described in Examples 258 and 259. A sample is removed and centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. A new IPLC peak containing glycopeptide antibiotic 262c with a molecular weight that is predicted if p-chloro-DL-phenylalanine is incorporated in place of phenylalanine is identified.

EXAMPLE (262c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 707 (m.w.=1412)

EXAMPLE 263

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING (S)-(−)-alpha-AMINOCYCLOHEXANE-PROPIONIC ACID OR PRODUCED IN THE PRESENCE OF (S)-(−)-alpha-AMINOCYCLOHEXANE-PROPIONIC ACID

Cyclo[3-cyclohexylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolid in-4-yl)serylserylglycyl]

Approximately 10 L of supernatant of a 7-day fermentation of strain LL4728 supplemented with (S)-(−)-alpha-aminocyclohexane-propionic acid, conducted as described in Examples 258 and 259, is loaded onto an XAD-7 column (1.2 L). The column is sequentially washed with water (4 L), methanol (3 L), and water (3 L) followed by elution with 1:1 acetonitrile in water containing 0.15% trifluoroacetic acid (4 L). The acidic acetonitrile/water fraction is concentrated under reduced pressure to a small volume and lyophilized to dryness affording a brown powder. The brown powder is then extracted with 1:4 water/dimethylformamide, and the extract is fractionated by reverse phase HPLC on a C18 column (YMC ODS-A, 10 micron particle size, 70×500 mm). The mobile phase consists of a gradient from 12 to 40% by volume of acetonitrile in water with 0.02% trifluoroacetic acid over 40 min at a flow rate of 100 mL per min. The peak fraction with a retention time of approximately 29 min is concentrated and re-purified by reverse phase HPLC on another C18 column (MetaChem ODS3, 5 micron particle size, 20×250 mm). The mobile phase is a gradient solvent system from 20 to 50% by volume of acetonitrile in water with 0.02% trifluoroacetic acid over 41 min at a flow rate of 7 mL per min. The peak fraction at approximately 41 min affords Example 263 upon evaporation.

EXAMPLE (263)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 644.4 (m.w.=1286)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLES 264a AND 264b

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING m-FLUORO-DL-PHENYLALANINE

EXAMPLE 264a

Cyclo[glycyl-3-fluoro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 264b

Cyclo[glycyl-3-fluoro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl )seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

Approximately 10 L of supernatant from a 7-day fermentation of strain LL4690 supplemented with m-fluoro-DL-phenylalanine, conducted as described in Examples 258 and 259, is processed using an XAD-7 column, and the fraction concentrate that contained the glycopeptide antibiotics is extracted with 1:4 water/dimethylformamide, as described in Example 261. The extract is fractionated by reverse phase HPLC on a C18 column (YMC ODS-A, 10 micron particle size, 70×500). The mobile phase is a gradient solvent system from 20 to 35% acetonitrile in water with 0.02% trifluoroacetic acid over 55 min at flow rate of 100 mL per min. The peak fractions with retention times at approximately 38 and 46 min afford Examples 264a and 264b, respectively, upon evaporation of volatiles.

EXAMPLE (264a)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 699.4 (m.w.=1396)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE (264b)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 699.4 (m.w.=1396)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE 264c

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING m-FLUORO-DL-PHENYLALNINE

Cyclo[glycyl-3-fluoro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl- 2-iminoimidazolidin-4-yl)serylseryl]

A 50 mL fermentation of strain LL4690 supplemented with m-fluoro-DL-phenylalanine is performed as described in Examples 258 and 259. A sample is removed and centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. A new HPLC peak containing glycopeptide antibiotic 264c with a molecular weight that is predicted if m-fluoro-DL-phenylalanine is incorporated in place of phenylalanine is identified.

EXAMPLE (264c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 657 (m.w.=1312)

EXAMPLES 265a AND 265b

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING 3-(2-THIENYL)-DL-ALANINE

Cyclo[3-(2-thienyl)-2-aminobutanoyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]

EXAMPLE 265b

Cyclo[3-(2-thienyl)-2-aminobutanoyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylserylglycyl]

Approximately 10 L of supernatant from a 7-day fermentation of strain LL4690 supplemented with 3-(2-thienyl)-DL-alanine, conducted as described in Examples 258 and 259, is processed using an XAD-7 column. The fraction concentrate containing the glycopeptide antibiotics is extracted with 1:4 water/dimethylformamide, as described in Example 261. The extract is fractionated by reverse phase HPLC on a C18 column (YMC ODS-A, 10 micron particle size, 70×500). The mobile phase is a gradient solvent system from 20 to 35% acetonitrile in water with 0.02% trifluoroacetic acid over 55 min at flow rate of 100 mL per min. The peak fractions with retention times at approximately 27 and 33 min afford Examples 265a and 265b, respectively, upon evaporation of volatiles.

EXAMPLE (265a)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 693.4 (m.w.=1384)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE (265b)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 693.4 (m.w.=1384)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE 265c

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING 3-(2-THIENYL)-DL-ALANINE

Cyclo[3-(2-thienyl)-2-aminobutanoyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl-2-imin oimidazolidin-4-yl)serylserylglycyl]

A 50 mL fermentation of strain LL4690 supplemented with 3-(2-thienyl)-DL-alanine is performed as described in Examples 258 and 259. A sample is centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. A new HPLC peak containing glycopeptide antibiotic 265c with a molecular weight that is predicted if 3-(2-thienyl)-DL-alanine is incorporated in place of phenylalanine is identified.

EXAMPLE (265c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 651 (m.w.=1300)

EXAMPLE 266a. 266b AND 266c

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING m-FLUORO-DL-TYROSINE

EXAMPLE 266a

Cyclo[glycyl-β-methylphenylalanyl-3-fluoro-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 266b

Cyclo[glycyl-β-methylphenylalanyl-3-fluoro-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 266c

Cyclo[glycyl-β-methylphenylalanyl-3-fluoro-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A 50 mL fermentation of strain LL4690 supplemented with m-fluoro-DL-tyrosine is performed as described in Examples 258 and 259. A sample is centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. New HPLC peaks containing glycopeptide antibiotics 266a, 266b, and 266c with molecular weights predicted if m-fluoro-DL-tyrosine is incorporated in place of tyrosine are identified.

EXAMPLE (266a)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 657 (m.w.=1312)

EXAMPLE (266b)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 699 (m.w.=1396)

EXAMPLE (266c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 699 (m.w.=1396)

EXAMPLE 267a, 267b AND 267c

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING 3-AMINO-L-TYROSINE

EXAMPLE 267a

Cyclo[glycyl-β-methylphenylalanyl-3-amino-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl- 2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 267b

Cyclo[glycyl-β-methylphenylalanyl-3-amino-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 267c

Cyclo[glycyl-β-methylphenylalanyl-3-amino-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)s eryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A 50 mL fermentation of strain LL4728 supplemented with 3-amino-L-tyrosine is performed as described in Examples 258 and 259. A sample is centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in

EXAMPLE 260b

New HPLC peaks containing glycopeptide antibiotics 267a, 267b, and 267c with molecular weights predicted if 3-amino-L-tyrosine is incorporated in place of tyrosine are identified.

EXAMPLE (267a)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 655.5 (m.w.=1309)

EXAMPLE (267b)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 697.5 (m.w.=1393)

EXAMPLE (267c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 697.5 (m.w.=1393)

EXAMPLE 268

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING S-(+)-PHENYLGLYCINE

Cyclo[glycyl-phenylglycyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopy ranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A 50 mL fermentation of strain LL4728 supplemented with S-(+)-phenylglycine is performed as described in Examples 258 and 259. A sample is centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. A new HPLC peak containing glycopeptide antibiotic 268 with a molecular weight predicted if S-(+)-phenylglycine is incorporated in place of phenylalanine is identified.

EXAMPLE (268)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 676 (m.w.=1350)

EXAMPLE 269a, 269b AND 269c

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING O-CHLORO-PHENYLALANINE

EXAMPLE 269a

Cyclo[glycyl-2-chloro-β-methylphenylalanyl-O-(4-O-hexopyranosylhexopyranosyl)tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3-(3-hexopyranosyl -2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 269b

Cyclo[glycyl-2-chloro-β-methylphenylalanyl-O-[4-O-[2-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 269c

Cyclo[glycyl-2-chloro-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylbutanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl) seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A 50 mL fermentation of strain LL4728 supplemented with o-chloro-phenylalanine is performed as described in Examples 258 and 259. A sample is centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. New HPLC peaks containing glycopeptide antibiotics 269a, 269b, and 269c with molecular weights predicted if o-chloro-phenylalanine is incorporated in place of phenylalanine are identified.

EXAMPLE (269a)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 665 (m.w.=1328)

EXAMPLE (269b)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 707 (m.w.=1412)

EXAMPLE (269c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 707 (m.w.=1412)

EXAMPLES 270a AND 270b

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING 4-METHYL-VALERIC ACID

EXAMPLE 270a

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[2-O-(4-methylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 270b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-acetyl-3-O-(4-methylpentanoylhexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-y l)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

Approximately 45 L of supernatant from a 7-day fermentation of strain LL-4690 supplemented with 4-methyl-valeric acid, conducted as described in Examples 258 and 259, is processed using an XAD-7 column. The fraction concentrate containing glycopeptide antibiotics is extracted with 1:4 water/dimethylformamide, as described in example 261. The extract is fractionated by reverse phase HPLC on a C18 column (YMC ODS-A, 10 micron particle size, 70×500). The mobile phase consists of a gradient solvent system from 10 to 40% acetonitrile in water with 0.02% trifluoroacetic acid over 62 min at flow rate of 100 mL per min. The broad fraction with a retention time of approximately 58 min is concentrated, and the residue is re-purified on a C18 column (MetaChem ODS3, 5 micron particle size, 20×250 mm). The mobile phase is a stepwise solvent system of 21% acetonitrile in water over the first 45 min and 23% acetonitrile in water over the next 25 min, both with 0.02% trifluoroacetic acid and at a flow rate of 7 mL per min. The peak fractions at approximately 19 and 63 min afford 270a and 270b upon evaporation of volatiles.

EXAMPLE (270a)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 697.5 (m.w.=1392)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE (270b)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 718.5 (m.w.=1434)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE 270c

GLYCOPEPTIDE ANTIBOTICS INCORPORATING 4-METHYL-VALERIC ACID

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(4-methylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

A 50 mL fermentation of strain LL4666 supplemented with 4-methyl-valeric is performed as described in Examples 258 and 259. A sample is centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. A new HPLC peak containing glycopeptide antibiotic 270c with a molecular weight predicted if 4-methyl-valeric acid is incorporated in place of isovaleric acid is identified.

EXAMPLE (270c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 697 (m.w.=1392)

EXAMPLE 271a

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING 3-METHYL-VALERIC ACID

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[3-O-(3-methylpentanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3- (3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

Approximately 10 L of supernatant from a 7-day fermentation of strain LL-4690 supplemented with 3-methyl-valeric acid, conducted as described in Examples 258 and 259, is processed using an XAD-7 column. The fraction concentrate that contained glycopeptide antibiotics is extracted with 1:4 water/dimethylformamide, as described in example 261. The extract is fractionated by reverse phase HPLC on a C18 column (YMC ODS-A, 10 micron particle size, 70×500). The mobile phase consisted of a gradient solvent system from 20 to 40% acetonitrile in water with 0.02% trifluoroacetic acid over 55 min at flow rate of 100 mL per min. The peak fraction at approximately 43 min affords Example 271a upon evaporation.

EXAMPLE (271a)

a) Molecular Weight: MS(ESI) [M+2H]2+=M/Z 697 (m.w.=1392)

b) The structure is consistent with the Proton Magnetic Resonance Spectral data (300 MHz, CD3OD/D2O 1:1)

EXAMPLE 271b AND 271c

GLYCOPEPTIDE ANTIBIOTICS INCORPORATING 3-METHYL-VALERIC ACID

EXAMPLE 271b

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[6-O-acetyl-3-O-(3-methylpentanoyl)hexopyranosyl]hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4- yl)seryl-3-(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

EXAMPLE 271c

Cyclo[glycyl-β-methylphenylalanyl-O-[4-O-[4-O-(3-methylpentanoyl)hexopyranosyl]-hexopyranosyl]tyrosyl-3-(2-iminoimidazolidin-4-yl)seryl-3 -(3-hexopyranosyl-2-iminoimidazolidin-4-yl)serylseryl]

Fermentations in 50 mL volumes of strains LL4690 or LL4666 supplemented with 3-methyl-valeric acid are performed as described in Examples 258 and 259. A sample is centrifuged to remove the cells. The supernatant is analyzed by analytical HPLC and LC/MS as described in Example 260b. New HPLC peaks containing glycopeptide antibiotics 271b and 271c with molecular weights predicted if 3-methyl-valeric acid is incorporated in place of isovaleric acid are identified.

EXAMPLE (271b)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 718.5 (m.w.=1434)

EXAMPLE (271c)

Molecular Weight: MS(ESI) [M+2H]2+=M/Z 697 (m.w.=1392)

EXAMPLE 272a AND 272b

GLYCOPEPTIDE ANTIBIOTICS CONTAINING BUTYRATE INSTEAD OF ISOVALERATE

EXAMPLE 27