Highly Efficient Chemoenzymatic Synthesis of Methyl (R)‐o‐Chloromandelate, a Key Intermediate for Clopidogrel, via Asymmetric Reduction with Recombinant Escherichia coli
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70
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
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年份:
2010
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