V4140

Virginiamycin S₁

≥99% (HPLC)

• Sinónimos: dihydro virginiamycin S1, Antibiotic 899, Staphylomycin S
• Fórmula empírica (notación de Hill): C₄₃H₄₉N₇O₁₀
• Número de CAS: 23152-29-6
• Peso molecular: 823.89
• Número CE: 245-462-6
• Código UNSPSC: 51283805
• ID de la sustancia en PubChem: 329829048
• NACRES: NA.85

Propiedades

• origen biológico: Streptomyces virginiae
• Nivel de calidad: 100
• Análisis: ≥99% (HPLC)
• formulario: solid
• condiciones de almacenamiento: (Keep container tightly closed in a dry and well-ventilated place.)
• color: white
• espectro de actividad antibiótica: Gram-positive bacteria
• Modo de acción: protein synthesis | interferes
• temp. de almacenamiento: −20°C
• cadena SMILES: 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
• Clave InChI: FEPMHVLSLDOMQC-IYPFLVAKSA-N

Descripción

Descripción general

Chemical structure: macrolide

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Nota de preparación

Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.

Otras notas

Keep container tightly closed in a dry and well-ventilated place.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable