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Key Documents

V2753

Sigma-Aldrich

Virginiamycin M1

≥95% (HPLC)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C28H35N3O7
Número CAS:
Peso molecular:
525.59
Número CE:
Número MDL:
Código UNSPSC:
51283805
ID de substância PubChem:
NACRES:
NA.85

fonte biológica

Streptomyces virginiae

Nível de qualidade

Ensaio

≥95% (HPLC)

forma

powder

condição de armazenamento

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

cor

white to yellow

solubilidade

methanol: soluble 10 mg/mL

espectro de atividade do antibiótico

Gram-positive bacteria

Modo de ação

protein synthesis | interferes

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

DAIKHDNSXMZDCU-QHKJSJJMSA-N

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). 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.

Ações bioquímicas/fisiológicas

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.

Outras notas

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

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

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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Junling Dun et al.
Journal of bacteriology, 197(3), 441-450 (2014-11-19)
There are up to seven regulatory genes in the pristinamycin biosynthetic gene cluster of Streptomyces pristinaespiralis, which infers a complicated regulation mechanism for pristinamycin production. In this study, we revealed that PapR6, a putative atypical response regulator, acts as a
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Scientific reports, 7(1), 11017-11017 (2017-09-10)
Distillers grains are co-products of the corn ethanol industry widely used in animal feed. We examined the effects of erythromycin, penicillin, and virginiamycin at low concentrations reflective of those detected in distillers grains on bacterial resistance selection. At 0.1 µg/ml erythromycin
VisG is eβential for biosynthesis of virginiamycin S, a streptogramin type B antibiotic, as a provider of the nonproteinogenic amino acid phenylglycine
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Microbiology, 167, 3213-3220 (2011)
N Suzuki et al.
Antimicrobial agents and chemotherapy, 42(11), 2985-2988 (1998-10-31)
Virginiamycin M1 (VM1), produced by Streptomyces virginiae, is a polyunsaturated macrocyclic lactone antibiotic belonging to the virginiamycin A group. S. virginiae possesses an activity which stereospecifically reduces a 16-carbonyl group of VM1, resulting in antibiotically inactive 16R-dihydroVM1. The corresponding VM1

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