Development of an Amine Dehydrogenase for Synthesis of Chiral Amines

被引：206

作者：

Abrahamson, Michael J. ^{[1
]}

Vazquez-Figueroa, Eduardo ^{[1
]}

Woodall, Nicholas B. ^{[1
]}

Moore, Jeffrey C. ^{[2
]}

Bommarius, Andreas S. ^{[1
]}

机构：

[1] Georgia Inst Technol, Sch Chem & Biomol Engn, Petit Inst Bioengn & Biosci, Atlanta, GA 30332 USA

[2] Merck & Co Inc, Dept Proc Res, Merck Res Labs, Rahway, NJ 07065 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 16期

基金：

美国国家科学基金会;

关键词：

amine dehydrogenase; asymmetric synthesis; biocatalysis; chiral amines; directed evolution; PHENYLALANINE DEHYDROGENASE; ASYMMETRIC-SYNTHESIS; LEUCINE DEHYDROGENASE; BACILLUS-SPHAERICUS; REDUCTIVE AMINATION; TRANSAMINASES; BIOCATALYSIS; RESOLUTION; MECHANISM; RANGE;

D O I：

10.1002/anie.201107813

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A leucine dehydrogenase has been successfully altered through several rounds of protein engineering to an enantioselective amine dehydrogenase. Instead of the wild-type α-keto acid, the new amine dehydrogenase now accepts the analogous ketone, methyl isobutyl ketone (MIBK), which corresponds to exchange of the carboxy group by a methyl group to produce chiral (R)-1,3-dimethylbutylamine. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3969 / 3972

页数：4

共 39 条

[1] A ROLE FOR QUATERNARY STRUCTURE IN THE SUBSTRATE-SPECIFICITY OF LEUCINE DEHYDROGENASE [J].

BAKER, PJ ;

TURNBULL, AP ;

SEDELNIKOVA, SE ;

STILLMAN, TJ ;

RICE, DW .

STRUCTURE, 1995, 3 (07) :693-705

[2]

BLASER HU, 1995, CHIM OGGI, V13, P11

[3] 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

[4]

Breuer M., 2004, ANGEW CHEM, V116, P806, DOI DOI 10.1002/ANGE.200300599

[5] Rhodococcus L-phenylalanine dehydrogenase:: Kinetics, mechanism, and structural basis for catalytic specifity [J].

Brunhuber, NMW ;

Thoden, JB ;

Blanchard, JS ;

Vanhooke, JL .

BIOCHEMISTRY, 2000, 39 (31) :9174-9187

[6] An engineered mutant, L307V of phenylalanine dehydrogenase from Bacillus sphaericus:: high activity and stability in organic-aqueous solvent mixtures and utility for synthesis of non-natural L-amino acids [J].

Chen, Sihong ;

Engel, Paul C. .

ENZYME AND MICROBIAL TECHNOLOGY, 2007, 40 (05) :1407-1411

[7] Efficient screening for new amino acid dehydrogenase activity: Directed evolution of Bacillus sphaericus phenylalanine dehydrogenase towards activity with an unsaturated non-natural amino acid [J].

Chen, Sihong ;

Engel, Paul C. .

JOURNAL OF BIOTECHNOLOGY, 2009, 142 (02) :127-134

[8] Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].

Constable, David J. C. ;

Dunn, Peter J. ;

Hayler, John D. ;

Humphrey, Guy R. ;

Leazer, Johnnie L., Jr. ;

Linderman, Russell J. ;

Lorenz, Kurt ;

Manley, Julie ;

Pearlman, Bruce A. ;

Wells, Andrew ;

Zaks, Aleksey ;

Zhang, Tony Y. .

GREEN CHEMISTRY, 2007, 9 (05) :411-420

[9] Biocatalytic Routes to Optically Active Amines [J].

Hoehn, Matthias ;

Bornscheuer, Uwe T. .

CHEMCATCHEM, 2009, 1 (01) :42-51

[10] Determining a novel NAD+-dependent amine dehydrogenase with a broad substrate range from Streptomyces virginiae IFO 12827:: purification and characterization [J].

Itoh, N ;

Yachi, C ;

Kudome, T .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 10 (1-3) :281-290

← 1 2 3 4 →