101485-50-1

Basic information

• Product Name: DesvancosaMinyl VancoMycin
• Synonyms: DesvancosaMinyl VancoMycin;2'-O-De(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)vancomycin Trifluoroacetic Acid Salt Hydrates;2'-O-De(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)vancomycin
• CAS NO: 101485-50-1
• Molecular Formula: C₅₉H₆₂Cl₂N₈O₂₂
• Molecular Weight: 1306.06998
• Product Categories: Chiral Reagents;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 101485-50-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Density: 1.70±0.1 g/cm3(Predicted)
• PKA: 2.95±0.70(Predicted)
• CAS DataBase Reference: DesvancosaMinyl VancoMycin(CAS DataBase Reference)
• NIST Chemistry Reference: DesvancosaMinyl VancoMycin(101485-50-1)
• EPA Substance Registry System: DesvancosaMinyl VancoMycin(101485-50-1)

Safety Data

• Hazardous Substances Data: 101485-50-1(Hazardous Substances Data)

Usage

Uses

Vancomycin (V096500) impurity.

Upstream product

• 1404-93-9 vancomycin hydrochloride 
• 82198-76-3 vancomycin aglycon 
• 133-89-1 diphosphoric acid 1''-β-D-[1'']glucopyranosyl ester 2-(uridin-5'-yl)ester 
• 1404-90-6 vancomycin 
• 1404-93-9 vancomycin hydrochloride 

Downstream Products

• 82198-76-3 vancomycin aglycon 
• 1404-90-6 vancomycin 
• 118373-81-2 chloroorienticin B 

Relevant articles and documents

Total Syntheses and Initial Evaluation of [Ψ[C(=S)NH]Tpg4]vancomycin, [Ψ[=NH)NH]Tpg4]vancomycin, [Ψ[CH2NH]Tpg4]vancomycin, and Their (4-Chlorobiphenyl)methyl Derivatives: Synergistic Binding Pocket and Peripheral Modifications for the Glycopeptide Antibiotics

Full details of studies are disclosed on the total syntheses of binding pocket analogues of vancomycin bearing the peripheral l-vancosaminyl-1,2-d-glucosyl disaccharide that contain changes to a key single atom in the residue-4 amide (residue-4 carbonyl O → S, NH, H2) designed to directly address the underlying molecular basis of resistance to vancomycin. Also disclosed are studies piloting the late-stage transformations conducted on the synthetically more accessible C-terminus hydroxymethyl aglycon derivatives and full details of the peripheral chlorobiphenyl functionalization of all of the binding-pocket-modified vancomycin analogues designed for dual d-Ala-d-Ala/d-Ala-d-Lac binding. Their collective assessment indicates that combined binding pocket and chlorobiphenyl peripherally modified analogues exhibit a remarkable spectrum of antimicrobial activity (VSSA, MRSA, and VanA and VanB VRE) and impressive potencies against both vancomycin-sensitive and vancomycin-resistant bacteria (MICs = 0.06-0.005 and 0.5-0.06 μg/mL for the amidine and methylene analogues, respectively) and likely benefit from two independent and synergistic mechanisms of action, only one of which is dependent on d-Ala-d-Ala/d-Ala-d-Lac binding. Such analogues are likely to display especially durable antibiotic activity that is not prone to rapidly acquired clinical resistance. (Chemical Equation Presented).

Selective Cleavage of Vancosamine, Glucose, and N-Methyl-leucine from Vancomycin and Related Antibiotics

Reaction of vancomycin and related antibiotics with trifluoroacetic acid at -15 deg C for 40 h selectively cleaved the amino sugar vancosamine; the second sugar, glucose, was removed by reaction with trifluoroacetic acid at 50 deg C for 3 h, and the N-terminal leucine moiety was cleaved using the Edman degradation procedure.

METHODS OF USING SEMI-SYNTHETIC GLYCOPEPTIDES AS ANTIBACTERIAL AGENTS

Methods of using semi-synthetic glycopeptides of formula I-XIV having antibacterial activity are described.