title: Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase.
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).
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, P.O. Box 416, Chengdu 610041, China.
authors.forename: Yan-Jie
authors.initials: YJ
authors.lastname: Liu
authors.forename: Xiao-Qiong
authors.initials: XQ
authors.lastname: Pei
authors.forename: Hui
authors.initials: H
authors.lastname: Lin
authors.forename: Ping
authors.initials: P
authors.lastname: Gai
authors.forename: Yu-Chang
authors.initials: YC
authors.lastname: Liu
authors.forename: Zhong-Liu
authors.initials: ZL
authors.lastname: Wu
mesh_terms: D042402:Achromobacter / Q000201:enzymology* / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D000475:Alkenes / Q000378:metabolism*; D001711:Biotransformation; D003001:Cloning, Molecular; D016000:Cluster Analysis; D004269:DNA, Bacterial / Q000737:chemistry / Q000235:genetics; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D008969:Molecular Sequence Data; D044925:Oxidoreductases Acting on CH-CH Group Donors / Q000378:metabolism*; D010802:Phylogeny; D017422:Sequence Analysis, DNA; D017385:Sequence Homology; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004269:DNA, Bacterial; D044925:Oxidoreductases Acting on CH-CH Group Donors; C019367:2-enoate reductase