1990 Volume 54 Issue 7 Pages 1819-1827
A novel method for producing optically active 1, 2-diols 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 27.9 g/l of (S)-1, 2-pentanediol from 30g/l 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-alcohol 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.
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