52312-06-8

Basic information

• Product Name: (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS NO: 52312-06-8
• Molecular Weight: 348.379
• Mol File: 52312-06-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid(52312-06-8)
• EPA Substance Registry System: (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid(52312-06-8)

Safety Data

• Hazardous Substances Data: 52312-06-8(Hazardous Substances Data)

Upstream product

• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 40512-60-5 R-O-dichloroacetylmandeloyl chloride 
• 20698-91-3 (R)-methyl mandelate 

Relevant articles and documents

Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid

The influence of the substrate structure on the catalytic properties of penicillin G acylase (PGA) from Escherichia coli in kinetically controlled acylations has been studied. In particular, the affinity of different β-lactam nuclei towards the active site has been evaluated considering the ratio between the rate of synthesis (vs) and the rate of hydrolysis of the acylating ester (vhl). 7-Aminocephalosporanic acid (7-ACA) and 7-amino-3-(1-sulfomethyl-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (7-SACA) showed a good affinity for the active centre of PGA. The enzymatic acylation of these nuclei with R-methyl mandelate has been studied in order to evaluate different approaches for the enzymatic synthesis of cefonicid. The best results have been obtained in the acylation of 7-SACA. Cefonicid (8) was recovered from the reaction mixture as the disodium salt in 65% yield and about 95% of purity. Furthermore, through acylation of 7-ACA, a "one-pot" chemo-enzymatic synthesis was carried out starting from cephalosporin C using three enzymes in sequence: D-amino acid oxidase (DAO), glutaryl acylase (GA) and PGA. Cefonicid disodium salt was obtained in three steps, avoiding any intermediate purification, in 35% overall yield and about 94% purity. This approach presents several advantages compared with the classical chemical processes.