Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH

阅读量：

111

作者：

N Itoh，M Matsuda，M Mabuchi，T Dairi，J Wang

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摘要：

Phenylacetaldehyde reductase (PAR) produced by styrene-assimilating Corynebacterium strain ST-10 was used to synthesize chiral alcohols. This enzyme with a broad substrate range reduced various prochiral aromatic ketones and -ketoesters to yield optically active secondary alcohols with an enantiomeric purity of more than 98% enantiomeric excess (e.e.). The Escherichia coli recombinant cells which expressed the par gene could efficiently produce important pharmaceutical intermediates; ( R )-2-chloro-1-(3-chlorophenyl)ethanol (28 mg·mL 1 ) from m -chlorophenacyl chloride, ethyl ( R )-4-chloro-3-hydroxy butanoate) (28 mg·mL 1 ) from ethyl 4-chloro-3-oxobutanoate and ( S )- N-tert -butoxycarbonyl(Boc)-3-pyrrolidinol from N -Boc-3-pyrrolidinone (51 mg·mL 1 ), with more than 86% yields. The high yields were due to the fact that PAR could concomitantly reproduce NADH in the presence of 37% (v/v) 2-propanol in the reaction mixture. This biocatalytic process provided one of the best asymmetric reductions ever reported.

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关键词：

phenylacetaldehyde reductase NADH regeneration chiral alcohol asymmetric reduction Corynebacterium sp

DOI：

10.1046/j.1432-1033.2002.02899.x

被引量：

126

年份：

2010