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Bioreduction of methyl o-chlorobenzoylformate at 500ANBgANBLa1 without external cofactors for efficient production of enantiopure clopidogrel intermediate

Biocatalytic reduction of methyl o-chlorobenzoylformate (CBFM) provides a green and direct access to methyl (R)-o-chloromandelate [(R)-CMM], an intermediate for a platelet aggregation inhibitor named clopidogrel. As much as 500 g La1 of CBFM was stoichiometrically converted into enantiopure (R)-CMM...

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Bibliographic Details
Published in:Tetrahedron letters 2012-08, Vol.53 (35), p.4715-4717
Main Authors: Ni, Yan, Pan, Jiang, Ma, Hong-Min, Li, Chun-Xiu, Zhang, Jie, Zheng, Gao-Wei, Xu, Jian-He
Format: Article
Language:English
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Summary:Biocatalytic reduction of methyl o-chlorobenzoylformate (CBFM) provides a green and direct access to methyl (R)-o-chloromandelate [(R)-CMM], an intermediate for a platelet aggregation inhibitor named clopidogrel. As much as 500 g La1 of CBFM was stoichiometrically converted into enantiopure (R)-CMM at 20 degree C by using a whole-cell catalyst coexpressing an aldo-keto reductase from Bacillus sp. and a glucose dehydrogenase (GDH). In addition to the high productivity of 812 g La1 da1, this new whole-cell reduction is attractive by eliminating the need of an added external cofactor.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2012.06.097