V4140

Virginiamycin S₁

≥99% (HPLC)

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

Propriedades

• fonte biológica: Streptomyces virginiae
• Nível de qualidade: 100
• Ensaio: ≥99% (HPLC)
• forma: solid
• condição de armazenamento: (Keep container tightly closed in a dry and well-ventilated place.)
• cor: white
• espectro de atividade do antibiótico: Gram-positive bacteria
• Modo de ação: protein synthesis | interferes
• temperatura de armazenamento: −20°C
• cadeia de caracteres 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
• chave InChI: FEPMHVLSLDOMQC-IYPFLVAKSA-N

Descrição

Descrição geral

Chemical structure: macrolide

Aplicação

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.

Ações bioquímicas/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 preparo

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

Outras notas

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

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable