21102-49-8

Basic information

• Product Name: (-)-Virginiamycin M2
• Synonyms: (-)-Virginiamycin M2;(27R)-26,27-Dihydrovirginiamycin M2;Ostreogrycin G;Pristinamycin IIB;Virginiamycin M2;Volpristin
• CAS NO: 21102-49-8
• Molecular Formula: C28H37 N3 O7
• Molecular Weight: 527.6093
• Mol File: 21102-49-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 809.5°Cat760mmHg
• Flash Point: 443.3°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 1.11E-27mmHg at 25°C
• Refractive Index: 1.575
• PKA: 13.18±0.70(Predicted)
• CAS DataBase Reference: (-)-Virginiamycin M2(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Virginiamycin M2(21102-49-8)
• EPA Substance Registry System: (-)-Virginiamycin M2(21102-49-8)

Safety Data

• Hazardous Substances Data: 21102-49-8(Hazardous Substances Data)

Usage

Description

(-)-Virginiamycin M2 is a type A streptogramin antibiotic produced by Streptomyces virginiae. It is a mixture of closely related compounds, with the main component being virginiamycin M1. This antibiotic is characterized by its antimicrobial activity against a range of bacteria, including both Gram-positive and some Gram-negative species. Its mechanism of action involves the inhibition of protein synthesis in bacteria, ultimately leading to their death.

Uses

Used in Veterinary Medicine:
(-)-Virginiamycin M2 is used as a preventive and treatment agent for infections in livestock. Its broad-spectrum antimicrobial activity makes it effective against various bacterial infections that can affect the health and productivity of animals in the industry.
Used in Human Medicine (with limitations):
While (-)-Virginiamycin M2 has shown potential for use in human medicine, its application is limited due to concerns about the development of antibiotic resistance and potential side effects. Further research and development are necessary to explore its potential uses in treating human infections while mitigating these risks.

InChI:InChI=1/C28H37N3O7/c1-17(2)26-19(4)7-8-24(34)29-10-5-6-18(3)12-21(32)13-22(33)14-25-30-23(16-37-25)27(35)31-11-9-20(15-31)28(36)38-26/h5-8,12,16-17,19-21,26,32H,9-11,13-15H2,1-4H3,(H,29,34)/b6-5+,8-7+,18-12+/t19-,20+,21-,26-/m1/s1

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Relevant articles and documents

Synthetic group A streptogramin antibiotics that overcome Vat resistance

Natural products serve as chemical blueprints for most antibiotics in clinical use. The evolutionary process by which these molecules arise is inherently accompanied by the co-evolution of resistance mechanisms that shorten the clinical lifetime of any given class of antibiotics1. Virginiamycin acetyltransferase (Vat) enzymes are resistance proteins that provide protection against streptogramins2, potent antibiotics against Gram-positive bacteria that inhibit the bacterial ribosome3. Owing to the challenge of selectively modifying the chemically complex, 23-membered macrocyclic scaffold of group A streptogramins, analogues that overcome the resistance conferred by Vat enzymes have not been previously developed2. Here we report the design, synthesis, and antibacterial evaluation of group A streptogramin antibiotics with extensive structural variability. Using cryo-electron microscopy and forcefield-based refinement, we characterize the binding of eight analogues to the bacterial ribosome at high resolution, revealing binding interactions that extend into the peptidyl tRNA-binding site and towards synergistic binders that occupy the nascent peptide exit tunnel. One of these analogues has excellent activity against several streptogramin-resistant strains of Staphylococcus aureus, exhibits decreased rates of acetylation in vitro, and is effective at lowering bacterial load in a mouse model of infection. Our results demonstrate that the combination of rational design and modular chemical synthesis can revitalize classes of antibiotics that are limited by naturally arising resistance mechanisms.

METHODS OF MAKING STREPTOGRAMIN COMPOSITIONS AND THE USE THEREOF

Disclosed herein, inter alia, are methods of making and using streptogramin compositions.

Total synthesis of (-)-virginiamycin m2: Application of crotylsilanes accessed by enantioselective Rh(II) or Cu(I) promoted carbenoid Si-H insertion

A stereoselective synthesis of the antibiotic (-)-virginiamycin M 2 is detailed. A convergent strategy was utilized that proceeded in 10 steps (longest linear sequence) from enantioenriched silane (S)-15. This reagent, which was prepared via a Rh(II)- or Cu(I)-catalyzed carbenoid Si-H insertion, was used to introduce the desired olefin geometry and stereocenters of the C1-C5 propionate subunit. A modified Negishi cross-coupling or an efficient alkoxide-directed titanium-mediated alkyne-alkyne reductive coupling strategy was utilized to assemble the trisubstituted (E,-E)-diene. An underutilized late-stage SmI2-mediated macrocyclization was employed to construct the 23-membered macrocycle scaffold of the natural product (Figure presented).