Asymmetric reductinon of carbonyl compounds by yeast. II. Preparation of optically active α- and β-hydroxy carboxylic acid derivatives

Abstract

α- and β-Keto esters and amides are readily reduced by an actively fermenting mutant of Saccharomyces cerevisiae and produce optically active α- and β-hydroxy esters and amides in moderate yields. Typically, methyl 2-oxo-2-phenylacetate gave methyl (R)-(-)-2-hydroxy- 2-phenyl- acetate; 2-oxo-2-phenylacetamide gave (R)-(-)-2-hydroxy-2- phenylacetamide; ethyl benzoylacetate gave ethyl (S)-(-)-3-hydroxy-3- phenylpropionate, and ethyl 2-oxocyclohexanecarboxylate gave ethyl (1R,2S)-(+)-2-hydroxycyclohexanecarboxylate. In each case, the product obtained was optically pure. However, the reduction of ethyl pyruvate to ethyl lactate produced partially racemized products.