3-Halovinylglycines. Efficient irreversible inhibitors of Escherichia coli alanine racemase

…, WJ Greenlee, AA Patchett, EH Cordes

Index: Thornberry, N. A.; Bull, H. G.; Taub, D.; Greenlee, W. J.; Patchett, A. A.; Cordes, E. H. Journal of the American Chemical Society, 1987 , vol. 109, # 24 p. 7543 - 7544

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Citation Number: 26

Abstract

We wish to report that 3-halovinylglycines 1 are a new class of potent mechanism-based irreversible inactivators of alanine racemase. Our results with Escherichia coli B alanine racemase indicate that nearly every catalytic event results in irreversible inactivation of the enzyme. In contrast, mechanism-based inactivation by previously studied p-substituted alanines is much less efficient, requiring approximately 800 turnovers with this enzyme to ...