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

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 15期

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

页码：2539 / 2549

页数：11

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 [J].

BOCK, K ;

LUNDT, I ;

PEDERSEN, C .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1983, 37 (04) :341-344

[2] LACTOBACILLUS-KEFIR ALCOHOL-DEHYDROGENASE - A USEFUL CATALYST FOR SYNTHESIS [J].

BRADSHAW, CW ;

HUMMEL, W ;

WONG, CH .

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 [J].

BRADSHAW, CW ;

FU, H ;

SHEN, GJ ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1526-1532

[4] Industrial methods for the production of optically active intermediates [J].

Breuer, M ;

Ditrich, K ;

Habicher, T ;

Hauer, B ;

Kesseler, M ;

Stürmer, R ;

Zelinski, T .

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 [J].

Easwar, S ;

Argade, NP .

TETRAHEDRON-ASYMMETRY, 2003, 14 (03) :333-337

[6] Rapid identification of enantioselective ketone reductions using targeted microbial libraries [J].

Homann, MJ ;

Vail, RB ;

Previte, E ;

Tamarez, M ;

Morgan, B ;

Dodds, DR ;

Zaks, A .

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 [J].

Hummel, W .

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 [J].

Inoue, K ;

Makino, Y ;

Itoh, N .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2005, 71 (07) :3633-3641

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