Virginiamycin M1
SIGMA/V2753 - ≥95% (HPLC)
Synonym: Ostreogrycin A; Pristinamycin IIA; Staphylomycin M1; Streptogramin A; Virginiamycin M1; Mikamycin A; Staphylomycin
CAS Number: 21411-53-0
Empirical Formula (Hill Notation): C28H35N3O7
Molecular Weight: 525.59
EC Number: 244-376-6
MDL Number: MFCD00869411
Linear Formula: C28H35N3O7
Product Type: Chemical
antibiotic activity spectrum | Gram-positive bacteria |
assay | ≥95% (HPLC) |
biological source | Streptomyces virginiae |
color | white to yellow |
form | powder |
InChI | 1S/C28H35N3O7/c1-17(2)26- |
InChI key | DAIKHDNSXMZDCU-QHKJSJJMSA |
mode of action | protein synthesis | interferes |
Quality Level | 200 |
SMILES string | CC(C)[C@H]1OC(=O)C2=CCCN2 |
solubility | methanol: soluble 10 mg/mL |
storage condition | (Keep container tightly closed in a dry and well-ventilated place.) |
storage temp. | 2-8°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). VM1 is a polyunsaturated macrocyclic petolide. VM1 and VS 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. They are chemically modified to make therapeutic drugs such as quinupristin and dalfopristin. |
Biochem/physiol Actions: | Virginiamycin M1 inhibits bacterial protein synthesis at the level of aminoacyl-tRNA binding and peptide bond formation. It inactivates the 50S ribosome. S. virginiae inactivates VM1 by reducing its 16-carbonyl group, forming 16R-dihydroVM1. VM1 reductase participates solely in VM1 inactivation in vivo. |
General description: | Chemical structure: macrolide |
Other Notes: | Keep container tightly closed in a dry and well-ventilated place. |
Packaging: | 5, 10 mg in serum bottle |
RIDADR | NONH for all modes of transport |
WGK Germany | WGK 3 |
Flash Point(F) | Not applicable |
Flash Point(C) | Not applicable |
Purity | ≥95% (HPLC) |
Storage Temp. | 2-8°C |
UNSPSC | 51101500 |