Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 13, Pages 2039-2044Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800292
Keywords
asymmetric catalysis; biotransformations; chemoenzymatic synthesis; enzyme catalysis
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Funding
- Japan Society for the Promotion of Science (JSPS)
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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 degrees C on a 2-g scale (1.0M). 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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