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[1]杨忠华,王玉,曾嵘,等.利用微生物重组技术促进羰基不对称还原研究进展[J].生物加工过程,2009,7(06):8-14.
 YANG Zhong-hua,WANG Yu,ZENG Rong,et al.Recent progress of asymmetric reduction of ketones with microbial recombinant technology[J].Chinese Journal of Bioprocess Engineering,2009,7(06):8-14.
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利用微生物重组技术促进羰基不对称还原研究进展
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《生物加工过程》[ISSN:1672-3678/CN:32-1706/Q]

卷:
7
期数:
2009年06期
页码:
8-14
栏目:
出版日期:
2009-11-30

文章信息/Info

Title:
Recent progress of asymmetric reduction of ketones with microbial recombinant technology
文章编号:
1672-3678(2009)06-0008-07
作者:
杨忠华1王玉1曾嵘2常煦1覃健1刘昶1
1. 武汉科技大学 化学工程与技术学院,武汉430081;
2. 湖北大学 化学化工学院,武汉430062
Author(s):
YANG Zhong-hua1 WANG Yu1 ZENG Rong2 CHANG Xu1 TAN Jian1 LIU Chang1
1. College of Chemical Engineering and Technology, Wuhan University of Science and Technology, Wuhan 430081, China;
2. Faculty of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, China
关键词:
不对称还原羰基还原重组微生物手性醇
分类号:
TQ033
文献标志码:
A
摘要:
手性醇是许多手性药物合成的关键手性砌块,利用微生物细胞催化相应前手性羰基化合物不对称还原, 是合成手性醇的重要方法之一。但应用野生微生物催化时,反应的时空产率、立体选择性较低。详细介绍了利用微生物重组技术以促进前手性羰基化合物不对称还原反应合成手性醇的国内外研究进展。从酶的种类、表达系统以及辅酶再生系统3个方面对重组细胞催化反应体系的构建进行了概述。同时按照反应底物的类型,对重组微生物在催化不同类型羰基化合物不对称还原合成手性醇中的应用分别进行了归纳和介绍。

参考文献/References:

[1]Hutt A J,Tan S C.Drug chirality and its clinical significance[J].Drugs,1996,52(5):1-12.
[2]Rouhi A M.Chiral business[J].Chem Eng News,2003,81(18):45-56.
[3]Rodrigues J A R,Moran P J S,Fardelone L C.Recent advances in the biocatalytic asymmetric reduction of acetophenones and α,β-unsaturated carbonyl compounds[J].Food Technol Biotechnol,2004,42(4):295-303.
[4]杨忠华,曾嵘,王光辉,等.立体选择性还原芳香酮微生物的筛选及反应特性的研究[J].精细化工,2007,24(5):466-469.
Yang Zhonghua,Zeng Rong,Wang Guanghui,et al.Isolation of microbe for asymmetric reduction of prochiral aromatic ketone and its reaction characters[J].Fine Chemicals,2007,24(5):466-469.
[5]欧阳立明,许建和.生物催化与生物转化研究进展[J].生物加工过程,2008,6(3):1-9.
Ouyang Liming,Xu Jianhe.Progress in biocatalysis and biotransformation[J].Chin J Biopro Eng,2008,6(3):1-9.
[6]Wei Z L,Li Z Y,Lin G Q.Baker′s yeast mediated mono-reduction of 1,3-cyclohexanediones bearing two identical C(2) substituents[J].Tetrahedron:Asymmetry,2001,12(2):229-233.
[7]Schmid A,Dordick J S,Hauer B,et al.Industrial biocatalysis today and tomorrow[J].Nature,2001,409:258-268.
[8]Nakamura K,Yamanaka R,Matsuda T,et al.Recent developments in asymmetric reduction of ketones with biocatalysts[J].Tetrahedron:Asymmetry,2003,14 (18):2659-2681.
[9]杨忠华,曾嵘,颜晓潮,等.酵母细胞不对称还原4-氯苯乙酮合成相应手性醇[J].精细化工,2007,24(1):6366.
Yang Zhonghua,Zeng Rong,Yan Xiaochao,et al.Asymmetric reduction of 4-chloroacetophenone to corresponding chiral alcoho catalyzed by Saccharomyces cerevisiae[J].Fine Chemicals,2007,24(1):63-66.
[10]Yang Z H,Zeng R,Wang Y,et al.Isolation of microbe for asymmetric reduction of prochiral aromatic ketone and its reaction characters[J].Front Chem Eng China,2007,1(4):416-420.
[11]Lavandera I,Hller B,Kern A,et al.Asymmetric anti-prelog reduction of ketones catalysed by Paracoccus pantotrophus and Comamonas sp. cells via hydrogen transfer[J].Tetrahedron:Asymmetry,2008,19(16):1954-1958.
[12]Yang G S,Ou Z M,Yao S J,et al.Asymmetric reduction of 3-chloropropiophenone to (S)-3-chloro-1-phenylpropanol using immobilized Saccharomyces cerevisiae CGMCC 2266 cells[J].J Mol Catal B:Enzym,2009,57(1/4):83-88.
[13]聂尧,徐岩.生物催化立体选择性氧化还原中存在问题及其发展策略[J].生物加工过程,2008,6(2):1-9.
Nie Yao,Xu Yan.Biocatalytic systems for stereoselective oxidoreduction:existing limitations and development strategies[J].Chin J Biopro Eng,2008,6(2):1-9.
[14]Rozzell J D.Commercial scale biocatalysis:myths and realities[J].Bioorg Med Chem,1999,7(10):2253-2261.
[15]杨忠华,曾嵘,姚善泾,等.不对称还原前手性芳香酮微生物的筛选及反应特性[J].生物加工过程,2008,6(1):32-36.
Yang Zhonghua,Zeng Rong,Yao Shanjing,et al.Screening of microbe for asymmetric reduction of prochiral aryl ketones and characterization of the reduction reaction[J].Chin J Biopro Eng,2008,6(1):32-36.
[16]Ford G,Ellis E M.Characterization of Ypr1p from Saccharomyces cerevisiae as a 2-methylbutyraldehyde reductase[J].Yeast,2002,19(12):1087-1096.
[17]敬科举,徐志南,林建平,等.重组大肠杆菌细胞不对称还原4-氯乙酰乙酸乙酯合成(R)-(+)-4-氯-3-羟基丁酸乙酯[J].催化学报,2005,26(11):993-998.
Jing Keju,Xu Zhinan,Lin Jianping,et al. Asymmetric reduction of ethyl 4-chloroacetoacetate to ethyl (R)-(+)-4-chloro-3-hydroxybutyrate by recombinant Escherichia coli[J].Chinese Journal of Catalysis,2005,26(11):993-998.
[18]Hanson R L,Goldberg S,Goswami A,et al.Purification and cloning of a ketoreductase used for the preparation of chiral alcohols[J].Adv Synth Catal,2005,347(7/8):1073-1080.
[19]Goldberg S L,Nanduri V B,Chu L,et al.Enantioselective microbial reduction of 6-oxo-8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione:cloning and expression of reductases[J].Enzyme Microb Technol,2006,39(7):1441-1450.
[20]Yasohara Y,Kizaki N,Hasegawa J.Stereoselective reduction of alkyl 3-oxobutanoate by carbonylreductase from Candida magnoliae[J].Tetrahedron:Asymmetry,2001,12(12):1713-1718.
[21]Hummel W,Abokitse K,Drauz K,et al.Towards a large-scale asymmetric reduction process with isolated enzymes:expression of an (S)-alcohol dehydrogenase in E.coli and studies on the synthetic potential of this biocatalyst[J].Adv Synth Catal,2003,345 (1/2):153-159.
[22]Itoh N,Matsuda M,Mabuchi M.Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH[J].Eur J Biochem,2002,269(9):2394-2402.
[23]Kataoka M,Hoshino-Hasegawa A,Thiwthong R,et al.Gene cloning of an NADPH-dependent menadione reductase from Candida macedoniensis,and its application to chiral alcohol production[J].Enzyme Microb Technol,2006,38(7):944-951.
[24]Katz M,Frejd T,Hahn-Hgerdal B,et al. Efficient anaerobic whole cell stereoselective bioreduction with recombinant Saccharomyces cerevisiae[J].Biotechnol Bioeng,2003,84(5):573-582.
[25]Inoue K,Makino Y,Dairi T,et al.Gene cloning and expression of Leifsonia alcohol dehydrogenase (LSADH) involved in asymmetric hydrogen-transfer bioreduction to produce (R)-form chiral alcohols[J].Biosci Biotechnol Biochem,2006,70(2):418-426.
[26]Ema T,Yagasaki H,Okita N,et al.Asymmetric reduction of ketones using recombinant E.coli cells that produce a versatile carbonyl reductase with high enantioselectivity and broad substrate specificity[J].Tetrahedron,2006,62(1):1-7.
[27]Matsuyama A,Yamamoto H,Kawada N.Industrial production of R-1,3-butanediol by new biocatalysts[J].J Mol Catal B:Enzym,2001,11(4/6):513-521.
[28]Stampfer W,Kosjek B,Faber K,et al.Biocatalytic asymmetric hydrogen transfer employing Rhodococcus ruber DSM 44541[J].J Org Chem,2003,68(2):402-406.
[29]Hildebrandt P,Riermeier T,Altenbuchner J,et al.Efficient resolution of prostereogenic arylaliphatic ketones using a recombinant alcohol dehydrogenase from Pseudomonas fluorescens[J].Tetrahedron:Asymmetry,2001,12(8):1207-1210.
[30]聂尧,徐岩,王海燕,等.重组大肠杆菌不对称还原2-羟基苯乙酮合成(R)-苯基乙二醇[J].化工进展,2006,25(10):1231-1236.
Nie Yao,Xu Yan,Wang Haiyan,et al.Synthesis of (R)-1-phenyl-1,2-ethanediol by stereospecific reduction of 2-hydroxyacetophenone using recombinant Escherichia coli expressing (R)-specific carbonyl reductase[J].Chemical Industry and Engineering Progress,2006,25(10):1231-1236.
[31]Xu N,Wang H Y,Nie Y,et al.Cloning and expression of the gene encoding (R)-specific carbonyl reductase from Candida parapsilosis CCTCC M203011[J].Front Biol China,2008,3(1):19-25.
[32]Kataoka M,Rohani L P S,Yamamoto K,et al.Enzymatic production of ethyl (R)-4-chloro-3-hydroxybutanoate:asymmetric reduction of ethyl 4-chloro-3-oxobutanoate by an Escherichia coli transformant expressing the aldehyde reductase gene from yeast[J].Appl Microbiol Biotechnol,1997,48(6):699-703.
[33]Matsuyama A,Yamamoto H,Kobayashi Y.Practical application of recombinant whole-cell biocatalysts for the manufacturing of pharmaceutical intermediates such as chiral alcohols[J].Org Process Res Dev,2002,6(4):558-561.
[34]Engelking H,Pfaller R,Wich G,et al.Reaction engineering studies on ketoester reductions with whole cells of recombinant Saccharomyces cerevisiae[J].Enzyme Microb Technol,2006,38(3/4):536-544.
[35]Kizaki N,Yasohara Y,Hasegawa J,et al.Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes[J].Appl Microbiol Biotechnol,2001,55(5):590-595.
[36]Maruyama R,Nishizawa M,Itoi Y,et al.The enzymes with benzil reductase activity conserved from bacteria to mammals[J].J Biotechnol,2002,94(2):157-169.
[37]Grger H,May O,Werner H,et al.A “second-generation process” for the synthesis of L-neopentylglycine:asymmetric reductive amination using a recombinant whole cell catalyst[J].Org Process Res Dev,2006,10(3):666-669.
[38]Hllrigl V,Hollmann F,Kleeb A C,et al.TADH,the thermostable alcohol dehydrogenase from Thermus sp.ATN1:a versatile new biocatalyst for organic synthesis[J].Appl Microbiol Biotechnol,2008,81(2):263-273.
[39]Brutigam S,Bringer-Meyer S,Weuster-Botz D.Asymmetric whole cell biotransformations in biphasic ionic liquid/water-systems by use of recombinant Escherichia coli with intracellular cofactor regeneration[J].Tetrahedron:Asymmetry,2007,18(16):1883-1887.
[40]Schroer K,Mackfeld U.Continuous asymmetric ketone reduction processes with recombinant Escherichia coli[J].J Biotechnol,2007,132(4):438-444.

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备注/Memo

备注/Memo:
收稿日期:2009-03-26
基金项目:湖北省自然科学基金资助项目(2008CDB354);武汉市青年科技晨光计划资助项目(200750731288)
作者简介:杨忠华(1976—),男,湖南怀化人,副教授,博士,研究方向:生物催化,E-mail:yangzhonghua76@wust.edu.cn
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