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V2753 Sigma-Aldrich

Virginiamycin M1

≥95% (HPLC)

Synonym: Mikamycin A, Staphylomycin

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z, Antibiotics by Mechanism of Action,
Quality Level   200
biological source   Streptomyces virginiae
assay   ≥95% (HPLC)
form   powder
color   white to yellow
solubility   methanol: soluble 10 mg/mL
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-positive bacteria
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

Description

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.

Packaging

5, 10 mg in serum bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

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Peer-Reviewed Papers
15

References

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