V4140
Virginiamycin S1
≥99% (HPLC)
Synonym(s):
dihydro virginiamycin S1, Antibiotic 899, Staphylomycin S
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About This Item
Empirical Formula (Hill Notation):
C43H49N7O10
CAS Number:
Molecular Weight:
823.89
EC Number:
UNSPSC Code:
51283805
PubChem Substance ID:
NACRES:
NA.85
biological source
Streptomyces virginiae
Quality Level
Assay
≥99% (HPLC)
form
solid
storage condition
(Keep container tightly closed in a dry and well-ventilated place.)
color
white
antibiotic activity spectrum
Gram-positive bacteria
Mode of action
protein synthesis | interferes
storage temp.
−20°C
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
General description
Chemical structure: macrolide
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.
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.
Preparation Note
Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.
Other Notes
Keep container tightly closed in a dry and well-ventilated place.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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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)
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
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