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V2753

Sigma-Aldrich

Virginiamycin M1

≥95% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C28H35N3O7
Numéro CAS:
21411-53-0
Poids moléculaire :
525.59
Numéro CE :
244-376-6
Numéro MDL:
MFCD00869411
Code UNSPSC :
51283805
ID de substance PubChem :
24900736
Nomenclature NACRES :
NA.85

Source biologique

Streptomyces virginiae

Niveau de qualité

200

Pureté

≥95% (HPLC)

Forme

powder

Conditions de stockage

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

Couleur

white to yellow

Solubilité

methanol: soluble 10 mg/mL

Spectre d'activité de l'antibiotique

Gram-positive bacteria

Mode d’action

protein synthesis | interferes

Température de stockage

2-8°C

Chaîne 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

Clé InChI

DAIKHDNSXMZDCU-QHKJSJJMSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
Beilei Ge et al.
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
Fitria Ningsih, Shigeru Kitani, et al.
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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