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
• 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

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.

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: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable