Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase

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Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase. / Liu, Yan Jie; Pei, Xiao Qiong; Lin, Hui; Gai, Ping; Liu, Yu Chang; Wu, Zhong Liu.

In: Applied Microbiology and Biotechnology, Vol. 95, No. 3, 08.2012, p. 635-645.

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Liu, Yan Jie ; Pei, Xiao Qiong ; Lin, Hui ; Gai, Ping ; Liu, Yu Chang ; Wu, Zhong Liu. / Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase. In: Applied Microbiology and Biotechnology. 2012 ; Vol. 95, No. 3. pp. 635-645.

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@article{ff5230a3839b42d89a266ce248b36d3e,
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)-{\ss}-aryl- {\ss}-cyano-propanoic acids, a precursor of (R)-?-amino butyric acids, including the pharmaceutically active enantiomer of the chiral drug (R)-baclofen with excellent enantioselectivity. It could catalyze aswell the stereoselective bioreduction of other activated alkenes such as cyclic imides, {\ss}-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).",
keywords = "Achromobacter sp., Activated alkene, Asymmetric reduction, Baclofen, Enoate reductase, Old yellow enzyme",
author = "Liu, {Yan Jie} and Pei, {Xiao Qiong} and Hui Lin and Ping Gai and Liu, {Yu Chang} and Wu, {Zhong Liu}",
year = "2012",
month = "8",
doi = "10.1007/s00253-012-4064-6",
language = "English",
volume = "95",
pages = "635--645",
journal = "Applied Microbiology & Biotechnology",
issn = "0175-7598",
number = "3",

}

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TY - JOUR

T1 - Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase

AU - Liu, Yan Jie

AU - Pei, Xiao Qiong

AU - Lin, Hui

AU - Gai, Ping

AU - Liu, Yu Chang

AU - Wu, Zhong Liu

PY - 2012/8

Y1 - 2012/8

N2 - 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)-ß-aryl- ß-cyano-propanoic acids, a precursor of (R)-?-amino butyric acids, including the pharmaceutically active enantiomer of the chiral drug (R)-baclofen with excellent enantioselectivity. It could catalyze aswell the stereoselective bioreduction of other activated alkenes such as cyclic imides, ß-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).

AB - 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)-ß-aryl- ß-cyano-propanoic acids, a precursor of (R)-?-amino butyric acids, including the pharmaceutically active enantiomer of the chiral drug (R)-baclofen with excellent enantioselectivity. It could catalyze aswell the stereoselective bioreduction of other activated alkenes such as cyclic imides, ß-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).

KW - Achromobacter sp.

KW - Activated alkene

KW - Asymmetric reduction

KW - Baclofen

KW - Enoate reductase

KW - Old yellow enzyme

UR - http://www.scopus.com/inward/record.url?scp=84864579521&partnerID=8YFLogxK

U2 - 10.1007/s00253-012-4064-6

DO - 10.1007/s00253-012-4064-6

M3 - Article

VL - 95

SP - 635

EP - 645

JO - Applied Microbiology & Biotechnology

JF - Applied Microbiology & Biotechnology

SN - 0175-7598

IS - 3

ER -

ID: 14582377