Alcohol-catalysed Hydrolysis of Benzylpenicillin

Andrew M. Davis; Philip Proctor; Michael I. Page

doi:10.1039/P29910001213

Alcohol-catalysed Hydrolysis of Benzylpenicillin

Andrew M. Davis, Philip Proctor, Michael I. Page

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

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 Brønsted β_nuc 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 is not a particularly effective acylating agent of alcohols.

Original language	English
Pages (from-to)	1213-1217
Number of pages	5
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	8
DOIs	https://doi.org/10.1039/P29910001213
Publication status	Published - Aug 1991

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abstract = "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 Br{\o}nsted 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 is not a particularly effective acylating agent of alcohols.",

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N2 - 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 Brønsted 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 is not a particularly effective acylating agent of alcohols.

AB - 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 Brønsted 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 is not a particularly effective acylating agent of alcohols.

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JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

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ER -

Alcohol-catalysed Hydrolysis of Benzylpenicillin

Abstract

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