Biotransformations of 2,3-epoxy-3-arylpropanenitriles by Debaryomyces hansenii and Mortierella isabellina cells

Abstract

Biotransformations of five substituted cis- and trans-oxiranecarbonitriles with Mortierella isabellina DSM 1414, a microbial whole-cell catalyst producing epoxide hydrolases, were investigated. The reactions were stopped when the conversion of the substrates reached 50%. They yielded the appropriate optically active dihydroxycarbonitriles and oxiranecarbonitriles in low enantiomeric purity. Kinetic resolution of rac- syn-2,3-dihydroxy-3-arylpropanenitriles by lipase catalyzed acetylation yielded almost enantiomerically pure (−)-dihydroxynitriles and mixtures of regioisomers of monoacetylated diols. Another microorganism, Debaryomyces hansenii DSM 3428, was used as a source of nitrile hydratases in the kinetic resolution of oxiranecarbonitriles. Only two trans-configured compounds were transformed into the corresponding oxiranecarboxamides.