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Merck
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安全信息

V4140

Sigma-Aldrich

Virginiamycin S1

≥99% (HPLC)

别名:

dihydro virginiamycin S1, Antibiotic 899, Staphylomycin S

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About This Item

经验公式（希尔记法）:
C43H49N7O10
CAS号:
23152-29-6
分子量:
823.89
EC 号:
245-462-6
UNSPSC代码:
51283805
PubChem化学物质编号:
329829048
NACRES:
NA.85

生物来源

Streptomyces virginiae

质量水平

100

检测方案

≥99% (HPLC)

形式

solid

储存条件

(Keep container tightly closed in a dry and well-ventilated place.)

颜色

white

抗生素抗菌谱

Gram-positive bacteria

作用机制

protein synthesis | interferes

储存温度

−20°C

SMILES字符串

CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]3CC(=O)CCN3C(=O)[C@H](Cc4ccccc4)N(C)C(=O)[C@@H]5CCCN5C1=O)c6ccccc6

InChI

1S/C43H49N7O10/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53)/t25-,29-,30+,31+,32+,34+,35+/m1/s1

InChI key

FEPMHVLSLDOMQC-IYPFLVAKSA-N

相关类别

一般描述

Chemical structure: macrolide

应用

The antibiotic virginiamycin is produced by Streptomyces virginiae and is a member of the virginiamycin family. Each member is produced as a mixture of two structurally different compounds that exhibit synergistic antibacterial activity. There are two groups: virginiamycin M1 (VM1) and virginiamycin S (VS). VS is a cyclic hexadepsipeptide. VS and VM1 are both used to inhibit protein synthesis since they are bacteriostatic. When used in combination they are more effective. Virginiamycin is used as a performance promoter in animal husbandry. It is chemically modified to make therapeutic drugs such as quinupristin and dalfopristin.

生化/生理作用

Virginiamycin S inhibits bacterial protein synthesis at the level of aminoacyl-tRNA binding and peptide bond formation. It inactivates the 50S ribosome. VS is a cyclic hexadepsipeptide containing a nonproteinogenic amino acid, Lphenylglycine (L-pheGly), in its core structure. The visG gene is required for VS biosynthesis. Nonribosomal peptide synthetase (NRPS) may be involved in VS biosynthesis. Virginiamycin S is active against Gram-positive bacteria.
Cyclic polypeptide antibiotic from Streptomyces sp. Acts as a synergist binding to the conformational change in the peptidyl transferase center fo the 50S ribosome.

制备说明

Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.

其他说明

Keep container tightly closed in a dry and well-ventilated place.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

监管及禁止进口产品

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N Suzuki et al.
Antimicrobial agents and chemotherapy, 42(11), 2985-2988 (1998-10-31)
Virginiamycin M1 (VM1), produced by Streptomyces virginiae, is a polyunsaturated macrocyclic lactone antibiotic belonging to the virginiamycin A group. S. virginiae possesses an activity which stereospecifically reduces a 16-carbonyl group of VM1, resulting in antibiotically inactive 16R-dihydroVM1. The corresponding VM1
VisG is eβential for biosynthesis of virginiamycin S, a streptogramin type B antibiotic, as a provider of the nonproteinogenic amino acid phenylglycine
Fitria Ningsih, Shigeru Kitani, et al.
Microbiology, 167, 3213 - 3220 (2011)

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