Structure-guided stereoselectivity inversion of a short-chain dehydrogenase/reductase towards halogenated acetophenones

被引:40
作者
Li, Aipeng [1 ]
Ye, Lidan [1 ,2 ]
Yang, Xiaohong [1 ]
Yang, Chengcheng [1 ]
Gu, Jiali [3 ]
Yu, Hongwei [1 ]
机构
[1] Zhejiang Univ, Coll Chem & Biol Engn, Inst Bioengn, Hangzhou 310027, Zhejiang, Peoples R China
[2] Zhejiang Univ, Minist Educ, Key Lab Biomass Chem Engn, Hangzhou 310027, Zhejiang, Peoples R China
[3] Huzhou Univ, Dept Chem Mat, Coll Life Sci, Huzhou 313000, Peoples R China
关键词
SECONDARY ALCOHOL-DEHYDROGENASE; CARBONYL REDUCTASE; ENANTIOSELECTIVITY; PRELOG; MUTATION; REDUCTIONS; ESTERASE;
D O I
10.1039/c6cc00051g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The structure-guided rational design of an NADH-dependent short-chain dehydrogenase/reductase (SDR) reversed the stereoselectivity towards halogenated acetophenones from Prelog to anti-Prelog. The enzyme-substrate interactions involving an aromatic ring and a halogen atom were proven to play critical roles in determining the stereoselectivity of these ketone reductions besides the steric repulsion.
引用
收藏
页码:6284 / 6287
页数:4
相关论文
共 27 条
[1]   Chemo-enzymatic synthesis of (R)- and (S)-3,4-dichlorophenylbutanolide intermediate in the synthesis of sertraline [J].
Barbieri, C ;
Caruso, E ;
D'Arrigo, P ;
Fantoni, GP ;
Servi, S .
TETRAHEDRON-ASYMMETRY, 1999, 10 (20) :3931-3937
[2]   Stereochemistry of Furfural Reduction by a Saccharomyces cerevisiae Aldehyde Reductase That Contributes to In Situ Furfural Detoxification [J].
Bowman, Michael J. ;
Jordan, Douglas B. ;
Vermillion, Karl E. ;
Braker, Jay D. ;
Moon, Jaewoong ;
Liu, Z. Lewis .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2010, 76 (15) :4926-4932
[3]   An expedient total synthesis of cis-(+)-Sertraline from D-phenylglycine [J].
Chandrasekhar, S ;
Reddy, MV .
TETRAHEDRON, 2000, 56 (08) :1111-1114
[4]   Regioselective o-Hydroxylation of Monosubstituted Benzenes by P450 BM3 [J].
Dennig, Alexander ;
Luelsdorf, Nina ;
Liu, Haifeng ;
Schwaneberg, Ulrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (32) :8459-8462
[5]   The role of reorganization energy in rational enzyme design [J].
Fuxreiter, Monika ;
Mones, Letif .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2014, 21 :34-41
[6]   The role of residue S139 of mandelate racemase: synergistic effect of S139 and E317 on transition state stabilization [J].
Gu, Jiali ;
Yu, Hongwei .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2012, 30 (05) :585-593
[7]   Controlling Enantioselectivity of Esterase in Asymmetric Hydrolysis of Aryl Prochiral Diesters by Introducing Aromatic Interactions [J].
Guo, Fei ;
Franzen, Stefan ;
Ye, Lidan ;
Gu, Jiali ;
Yu, Hongwei .
BIOTECHNOLOGY AND BIOENGINEERING, 2014, 111 (09) :1729-1739
[8]   Mutation of cysteine-295 to alanine in secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus affects the enantioselectivity and substrate specificity of ketone reductions [J].
Heiss, C ;
Laivenieks, M ;
Zeikus, JG ;
Phillips, RS .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (07) :1659-1666
[9]   Use of the anti-Prelog stereospecific alcohol dehydrogenase from Leifsonia and Pseudomonas for producing chiral alcohols [J].
Itoh, Nobuya .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2014, 98 (09) :3889-3904
[10]   Engineering the enantioselectivity of glutathione transferase by combined active-site mutations and chemical modifications [J].
Ivarsson, Ylva ;
Norrgard, Malena A. ;
Hellman, Ulf ;
Mannervik, Bengt .
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2007, 1770 (09) :1374-1381