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V2753

Virginiamycin M1

≥95% (HPLC)

Synonym(s):

Ostreogrycin A, Pristinamycin IIA, Staphylomycin M1, Streptogramin A, Virginiamycin M1, Mikamycin A, Staphylomycin

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About This Item

Empirical Formula (Hill Notation):
C28H35N3O7
CAS Number:
21411-53-0
Molecular Weight:
525.59
NACRES:
NA.85
PubChem Substance ID:
24900736
UNSPSC Code:
51283805
EC Number:
244-376-6
MDL number:
MFCD00869411
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biological source

Streptomyces virginiae

Quality Segment

assay

≥95% (HPLC)

form

powder

storage condition

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

color

white to yellow

solubility

methanol: soluble 10 mg/mL

antibiotic activity spectrum

Gram-positive bacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3

InChI

1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5-,10-9-,18-13-/t19-,20-,26-/m1/s1

InChI key

DAIKHDNSXMZDCU-QHKJSJJMSA-N

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). 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.

Other Notes

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

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type N95 (US)

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