Virginiamycin S₁

SIGMA/V4140 - ≥99% (HPLC)

Synonym: dihydro virginiamycin S1; Antibiotic 899; Staphylomycin S

CAS Number: 23152-29-6
Empirical Formula (Hill Notation): C₄₃H₄₉N₇O₁₀
Molecular Weight: 823.89
EC Number: 245-462-6
Linear Formula: C₄₃H₄₉N₇O₁₀
Product Type: Chemical

Catalog Number	PKG Qty.	Price	Quantity


45-V4140-5MG	5 mg	$471.00 1/EA		Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	Gram-positive bacteria
assay	≥99% (HPLC)
biological source	Streptomyces virginiae
color	white
form	solid
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
mode of action	protein synthesis \| interferes
Quality Level	100
SMILES string	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
storage condition	(Keep container tightly closed in a dry and well-ventilated place.)
storage temp.	−20°C

Application:	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.
Biochem/physiol Actions:	Cyclic polypeptide antibiotic from Streptomyces sp. Acts as a synergist binding to the conformational change in the peptidyl transferase center fo the 50S ribosome.
Biochem/physiol Actions:	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.
General description:	Chemical structure: macrolide
Other Notes:	Keep container tightly closed in a dry and well-ventilated place.
Packaging:	5 mg in serum bottle
Preparation Note:	Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥99% (HPLC)
Storage Temp.	−20°C
UNSPSC	51101500

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