Production of (R)-chiral alcohols by a hydrogen-transfer bioreduction with NADH-dependent Leifsonia alcohol dehydrogenase (LSADH)

被引:98
作者
Inoue, K [1 ]
Makino, Y [1 ]
Itoh, N [1 ]
机构
[1] Toyama Prefectural Univ, Biotechnol Res Ctr, Toyama 9390398, Japan
关键词
D O I
10.1016/j.tetasy.2005.06.036
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Alcohol dehydrogenase (LSADH) isolated from Leifsonia sp. S749 was used to produce (R)-chiral alcohols. The enzyme with a broad substrate range reduced various prochiral ketones and keto esters to yield optically active secondary alcohols with a high enantiomeric excess. LSADH transferred the pro-S hydrogen of NADH to the carbonyl moiety of phenyl trifluoromethyl ketone 13 through its re face to give (S)-1-pheilyl-2,2,2-trifluoroethatiol 40. LSADH was able to efficiently reproduce NADH when 2-propanol was used as a hydrogen donor in the reaction mixture. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2539 / 2549
页数:11
相关论文
共 38 条
  • [1] SYNTHESIS OF S-4-AMINO-3-HYDROXYBUTYRIC AND R-4-AMINO-3-HYDROXYBUTYRIC ACID (GABOB) AND S-CARNITINE AND R-CARNITINE FROM ARABINOSE OR ASCORBIC-ACID
    BOCK, K
    LUNDT, I
    PEDERSEN, C
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1983, 37 (04): : 341 - 344
  • [2] LACTOBACILLUS-KEFIR ALCOHOL-DEHYDROGENASE - A USEFUL CATALYST FOR SYNTHESIS
    BRADSHAW, CW
    HUMMEL, W
    WONG, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1532 - 1536
  • [3] A PSEUDOMONAS SP ALCOHOL-DEHYDROGENASE WITH BROAD SUBSTRATE-SPECIFICITY AND UNUSUAL STEREOSPECIFICITY FOR ORGANIC-SYNTHESIS
    BRADSHAW, CW
    FU, H
    SHEN, GJ
    WONG, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1526 - 1532
  • [4] Industrial methods for the production of optically active intermediates
    Breuer, M
    Ditrich, K
    Habicher, T
    Hauer, B
    Kesseler, M
    Stürmer, R
    Zelinski, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) : 788 - 824
  • [5] Amano PS-catalysed enantioselective acylation of (±)-α-methyl-1,3-benzodioxole-5-ethanol:: an efficient resolution of chiral intermediates of the remarkable antiepileptic drug candidate, (-)-talampanel
    Easwar, S
    Argade, NP
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (03) : 333 - 337
  • [6] Rapid identification of enantioselective ketone reductions using targeted microbial libraries
    Homann, MJ
    Vail, RB
    Previte, E
    Tamarez, M
    Morgan, B
    Dodds, DR
    Zaks, A
    [J]. TETRAHEDRON, 2004, 60 (03) : 789 - 797
  • [7] HUMMEL W, 1990, APPL MICROBIOL BIOT, V34, P15, DOI 10.1007/BF00170916
  • [8] Hummel W, 1997, Adv Biochem Eng Biotechnol, V58, P145
  • [9] Large-scale applications of NAD(P)-dependent oxidoreductases: recent developments
    Hummel, W
    [J]. TRENDS IN BIOTECHNOLOGY, 1999, 17 (12) : 487 - 492
  • [10] Purification and characterization of a novel alcohol dehydrogenase from Leifsonia sp strain S749:: a promising biocatalyst for an asymmetric hydrogen transfer bioreduction
    Inoue, K
    Makino, Y
    Itoh, N
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2005, 71 (07) : 3633 - 3641