An economical and convenient biocatalytic process was developed for the preparation of (S)-1-phenyl-1,2-ethanediol (PED),
which is a valuable chiral building block for pharmaceuticals
and liquid crystals, by stereoselective microbial conversion from
the corresponding racemate. As a result of screening bacteria,
yeasts, and molds, the enantioselective conversion of racemic
PED by Candida parapsilosis CCTCC M203011 was found to
be the most efficient process to produce (S)-PED with high
optical purity of 98% ee and yield of 92%. By detecting the
intermediate produced in the reaction by GC−MS, it was
suggested that (S)-enantiomer was produced from the intermediate identified as β-hydroxyacetophenone by asymmetric
reduction after stereoselective oxidation of (R)-enantiomer to
β-hydroxyacetophenone. After investigating the cofactor requirement and stereospecificity of the reaction catalyzed by the
cell-free extract from C. parapsilosis CCTCC M203011, it was
found that the stereoselective conversion involved the oxidation
of (R)-PED to the intermediate with NADP+ as the cofactor
and the reduction reaction that formed the product used NADH
as the cofactor, which was catalyzed by a novel cofactor-dependent oxidoreduction system. The NADP+-dependent (R)-specific alcohol dehydrogenase involved in stereoinversion was
purified from C. parapsilosis CCTCC M203011, which has a
relative molecular mass of 45kD.
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