Virginiamycin M1

• Catalog No.: V2753
• CAS Number: 21411-53-0
• M. F.: C28H35N3O7
• M. W.: 525.5934
• Purity: ~95%

SYNONYMS

• IUPAC name: (10R,11R,21S)-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone
• IUPAC Traditional name: (10R,11R,21S)-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone
• Synonyms: Staphylomycin; Mikamycin A

DATABASE IDS

• PubChem SID: 24900736
• MDL Number: MFCD00869411
• CAS Number: 21411-53-0
• EC Number: 244-376-6

PROPERTIES

• Empirical Formula (Hill Notation): C28H35N3O7
• Purity: ~95%
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C
• German water hazard class: 3

DETAILS

Description (English)

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 dalfopristin1.
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 vivo2.

Description (简体中文)

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 dalfopristin1.
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 vivo2.