High-Yield Production of Optically Active 1,2-Diols from the Corresponding Racemates by Microbial Stereoinversion

Abstract

A novel method for producing optically active 1,2-dioIs by microbial stereoinversion was developed. It was found that some microorganisms could convert only (R)-1,2-pentanediol in the racemate to the (S)-enantiomer. Candida parapsilosis produced 27.9g/1 of (S)-1,2-pentanediol from 30 g/I of the racemate in 24 hr of reaction (molar yield 93%, enantiomeric excess 100%). This stereoinversion proceeded via oxidation of (R)-1,2-pentanediol to 1-hydroxy-2-pentanone by an NAD+-linked (R)-specific alcohol dehydrogenase and reduction of 1-hydroxy-2-pentanone to (S)-1,2-pentanediol by an NADPH-linked (S)-specific 2-keto-1-alcohoI reductase. This microbial stereoinversion was applicable to ten 1,2-diols. Optically active 1,2-diols prepared by the reaction had the same configuration at the chiral center. © 1990, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.