V4140

Virginiamycin S₁

≥99% (HPLC)

• Synonym(s): dihydro virginiamycin S1, Antibiotic 899, Staphylomycin S
• Empirical Formula (Hill Notation): C₄₃H₄₉N₇O₁₀
• CAS Number: 23152-29-6
• Molecular Weight: 823.89
• EC Number: 245-462-6
• UNSPSC Code: 51283805
• PubChem Substance ID: 329829048
• NACRES: NA.85

Properties

• biological source: Streptomyces virginiae
• Quality Level: 100
• 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
• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable