Highly Efficient Chemoenzymatic Synthesis of Methyl (R)‐o‐Chloromandelate, a Key Intermediate for Clopidogrel, via Asymmetric Reduction with Recombinant Escherichia coli

阅读量:

70

作者:

T EmaS IdeN OkitaT Sakai

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摘要:

Methyl ( R )- o -chloromandelate [( R )- 1 ], which is an intermediate for a platelet aggregation inhibitor named clopidogrel, was obtained in >99% ee by the asymmetric reduction of methyl o -chlorobenzoylformate ( 2 ) with recombinant Escherichia coli overproducing a versatile carbonyl reductase. A remarkable temperature effect on productivity was observed in the whole-cell reduction of 2 , and the optimum productivity as high as 178 g/L was attained at 20 °C on a 2-g scale (1.0 M). The optimized reaction could be scaled up easily to transform 20 g of 2 in 100 mL of buffer. Three synthetic methods for 2 are compared.

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DOI:

10.1002/adsc.200800292

被引量:

175

年份:

2010

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来源期刊

Advanced Synthesis & Catalysis
2010/5/14 0:00:00

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2014
被引量:31

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