Enzymes in organic synthesis: oxidoreductions

Abstract

This article reviews the use of several oxidoreduction enzymes, including monooxygenases, chloroperoxidase, arene dioxygenase, lipoxygenase, galactose oxidase and alcohol dehydrogenases, in the preparation of optically pure or enriched epoxides, halohydrins, sulfoxides, hydroperoxides, alcohols, cyclohexadienediols, lactones and α-hydroxy aldehydes. The mechanisms of some of these enzyme-catalysed transformations, and their scopes and limitations in synthetic chemistry are also discussed. Representative syntheses of a key intermediate of 5-lipoxygenase inhibitor, a seven-carbon C-glycoside and an active component of the antibiotic bialaphos have been experimentally illustrated using Lactobacillus alcohol dehydrogenase, chloroperoxidase and glutamate dehydrogenase, respectively.