Abstract
The strain Achromobacter sp. JA81, which produced enoate reductase, was applied in the asymmetric reduction of activated alkenes. The strain could catalyze the bioreduction of alkenes to form enantiopure (R)-β-aryl-β-cyano-propanoic acids, a precursor of (R)-γ-amino butyric acids, including the pharmaceutically active enantiomer of the chiral drug (R)-baclofen with excellent enantioselectivity. It could catalyze as well the stereoselective bioreduction of other activated alkenes such as cyclic imides, β-nitro acrylates, and nitro-alkenes with up to >99 % ee and >99 % conversion. The draft genome sequencing of JA81 revealed six putative old yellow enzyme homologies, and the transcription of one of them, Achr-OYE3, was detected using reverse transcription polymerase chain reaction. The recombinant Escherichia coli expressing Achr-OYE3 displayed enoate reductase activity toward (Z)-3-cyano-3-phenyl-propenoic acid (2a).
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Acknowledgment
This work was supported by the National Natural Science Foundation of China (20802073 and 21072183), the 100 Talents Program and the West Light Foundation of the Chinese Academy of Sciences.
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Yan-Jie Liu and Xiao-Qiong Pei contributed equally to this study.
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Liu, YJ., Pei, XQ., Lin, H. et al. Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase. Appl Microbiol Biotechnol 95, 635–645 (2012). https://doi.org/10.1007/s00253-012-4064-6
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DOI: https://doi.org/10.1007/s00253-012-4064-6