Rearrangement of an isothiazolidinone to a β-lactam. A model for penicillin biosynthesis

CJ Easton

Index: Easton, Christopher J. Journal of the Chemical Society, Chemical Communications, 1983 , # 22 p. 1349 - 1350

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Citation Number: 6

Abstract

Based on novel syntheses of a /3-lactam from an isothiazolidinone, a mechanism of formation of the p-lactam ring in penicillin biosynthesis is proposed. ... Investigation of the biosynthesis of penicillins and related p-lactam antibiotics has shown that isopenicillin N (2) is derived from the tripeptide, [6-(~-cr-aminoadipoyl)J-~-cysteinyl- D-valine (l),l? but the mechanism of this transformation has not been elucidated. Although isothiazolidinones have been proposed as ...