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Key Documents

V2753

Sigma-Aldrich

Virginiamycin M1

≥95% (HPLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C28H35N3O7
Numero CAS:
Peso molecolare:
525.59
Numero CE:
Numero MDL:
Codice UNSPSC:
51283805
ID PubChem:
NACRES:
NA.85

Origine biologica

Streptomyces virginiae

Livello qualitativo

Saggio

≥95% (HPLC)

Forma fisica

powder

Condizioni di stoccaggio

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

Colore

white to yellow

Solubilità

methanol: soluble 10 mg/mL

Spettro attività antibiotica

Gram-positive bacteria

Modalità d’azione

protein synthesis | interferes

Temperatura di conservazione

2-8°C

Stringa SMILE

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
DAIKHDNSXMZDCU-QHKJSJJMSA-N

Descrizione generale

Chemical structure: macrolide

Applicazioni

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.

Azioni biochim/fisiol

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.

Altre note

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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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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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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