59054-27-2

Usage

Uses

Used in Pharmaceutical Industry:
(3S,5R,6R)-monomethyl benzylpenicilloate is used as an antibiotic for treating various bacterial infections. Its enhanced stability and broadened spectrum of activity make it an effective choice for combating a wide range of bacterial pathogens. The reduced risk of degradation by bacterial enzymes further contributes to its therapeutic success in treating infections.

Upstream product

• 52-67-5 3,3-dimethyl-D-cysteine 
• 854851-32-4 3-oxo-2-(2-phenyl-acetylamino)-propionic acid methyl ester 
• 67-56-1 methanol 
• 61-33-6 penicillin G 

Downstream Products

• 87492-68-0 (5R,6S,3S)-benzyl-D-penicilloic acid 

Relevant academic research and scientific papers

Thiazolidine Ring Opening in Penicillin Derivatives. Part 2. Enamine Formation

The alkaline hydrolysis of (3S,5R,6R)-methyl benzylpenicilloate, and the corresponding carboxamide and N-ethylamide, is accompanied by an absorbance increase at 285 nm.This is attributed to a competing elimination reaction across C6-C5 to open the thiazolidine ring and reversibly generate an enamine intermediate.Kinetic analysis and hydrolysis in D2O do not indicate a significant buildup of this intermediate during hydrolysis of the methyl ester.However, over the pH range 4-11 the rate of thiazolidine ring opening is competitive with hydrolysis of the ester function.The deuterium solvent kinetic isotope effect on the ring closure reaction is 7.5.

Comparison of the electrospray ionization (ESI) responses of penicillins with ESI responses of their methanolysis products

The electrospray ionization (ESI) responses, defined as the area of chromatographic peak of ion [M+H]+ obtained upon HPLC/ESI-MS analysis, of three β-lactam antibiotics, namely penicillin G, ampicillin and carbenicillin have been compared with

Alcohol-catalysed Hydrolysis of Benzylpenicillin

The hydrolysis of benzylpenicillin is catalysed by alkoxide ions and other oxygen bases.Catalysis occurs by a nucleophilic pathway and the intermediate ester can be detected in some cases.The Broensted βnuc for alkoxide ions is 0.97, and is compatible with rate-limiting ring opening of the β-lactam.A solvent isotope effect of 3.2 for the trifluoroethanol-catalysed reaction suggests protonation by water occurs to the departing β-lactam nitrogen.Penicillin in not a particularly effective acylating agent of alcohols.

Thiazolidine Ring Opening in Penicillin Derivatives. Part 1. Imine Formation

The rate of epimerisation of (3S,5R,6R)-benzylpenicilloic acid at C-5 shows three distinct dependencies upon pH in aqueous solution.Below pH 6 the rate shows a sigmoidal dependence upon pH, whereas it is pH-independent between pH 6 and 12, and above pH 12 the rate is hydroxide-ion dependent.These different regions of pH dependence are interpreted in terms of three mechanistic pathways all of which involve opening the thiazolidine ring by C-S bond fission and re-closure to generate the epimer.At low pH the reaction occurs by unimolecular ring opening of the S-conjugate acid which is kinetically equivalent to the N-conjugate acid of pKa 5.14.The pH-independent pathway involves formation of a zwitterion by unimolecular opening of the neutral thiazolidine.At high pH the unprotonated imine intermediate is formed by concerted hydroxide-ion-catalysed ring opening.The mono- and di-methyl esters of benzylpenicilloate also epimerise at C-5.At low pH the rates are similar for all three compounds but above pH 6 the mono- and di-esters are, respectively, 21 and 1700 times less reactive than the dianion of the diacid.