Enantioselective Reduction of α,β-Dehydro-α-amido Carboxylic Acid Derivatives by Ene-Reductases

Abstract

Enantioselective reduction of α,β-dehydro-α-amido carboxylic acid derivatives to optically active amido carboxylic acid derivatives has been carried out using whole-cell overexpressing ene-reductases (EREDs). The reduced products were obtained with good yields and excellent enantiomeric excesses of >99%. Among the enzymes tested, Seqenzym ene-reductase E4671 proved to be the most effective, accommodating methyl ester, free amide, and diverse N-protecting groups, as well as β-unsubstituted, β-methyl, and β-ethyl substituted substrates. Notably, the reaction is readily scalable.