|本期目录/Table of Contents|

[1]孔旭东,郁惠蕾,周佳海,等.环氧水解酶的结构基础及新酶开发[J].生物加工过程,2013,11(01):77-86.[doi:10.3969/j.issn.1672-3678.2013.01.014]
 KONG Xudong,YU Huilei,ZHOU Jiahai,et al.Structure basis of EHs and development of novel EHs as biocatalyst[J].Chinese Journal of Bioprocess Engineering,2013,11(01):77-86.[doi:10.3969/j.issn.1672-3678.2013.01.014]
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环氧水解酶的结构基础及新酶开发()
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《生物加工过程》[ISSN:1672-3678/CN:32-1706/Q]

卷:
11
期数:
2013年01期
页码:
77-86
栏目:
出版日期:
2008-01-30

文章信息/Info

Title:
Structure basis of EHs and development of novel EHs as biocatalyst
文章编号:
1672-3678(2013)01-0077-10
作者:
孔旭东12郁惠蕾1周佳海2许建和1
1. 华东理工大学 生物反应器工程国家重点实验室,上海 200237; 2. 中国科学院 上海有机化学研究所 生命有机化学国家重点实验室,上海 200036
Author(s):
KONG Xudong12YU Huilei1ZHOU Jiahai2XU Jianhe1
1. State Key Laboratory of Bioreactor Engineering,East China University of Science & Technology,Shanghai 200237,China; 2. State Key Laboratory of Bio-organic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry, Chinese Academy of Sc
关键词:
手性合成 环氧水解酶 结构基础 分子生物学
分类号:
Q78
DOI:
10.3969/j.issn.1672-3678.2013.01.014
文献标志码:
A
摘要:
环氧水解酶能应用于外消旋环氧化物的动力学拆分或对映归一性水解制备光学纯的环氧或邻位二醇,具有广阔的应用前景。近年来,多个环氧水解酶晶体结构的报道使人们对它的结构基础有了更深入的理解。随着基因信息的增长,分子生物学和蛋白质工程技术的发展大大简化了大量克隆表达多样性环氧水解酶的过程,降低了环氧水解酶分子改造的难度,为新型具有工业应用潜力的环氧水解酶的开发提供了技术支持。本文综述了环氧水解酶的结构与机制以及近年来环氧水解酶重组表达及分子改造的研究进展。

参考文献/References:

[1] Zelaszczyk D,Kiec-Kononowicz K.Biocatalytic approaches to optically active beta-blockers [J] . Curr Med Chem,2007,14:53-65.
[2] Agustian J,Kamaruddin A H,Bhatia S.Single enantiomeric beta-blockers:the existing technologies [J] . Process Biochem,2010,45:1587-1604.
[3] Choi W J,Choi C Y.Production of chiral epoxides:Epoxide hydrolase-catalyzed enantioselective hydrolysis [J] . Biotechnol Bioproc Eng,2005,10:167-179.
[4] Oesch F.Mammalian epoxide hydrases:inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds[J] . Xenobiotica,1973,3:305-340.
[5] Hammock B D,Gill S S,Stamoudis V,et al.Soluble mammalian epoxide hydratase:action on juvenile hormone and other terpenoid epoxides[J] . Comp Biochem Physiol B,1976,53:263-265.
[6] Nardini M,Ridder I S,Rozeboom H J,et al.The X-ray structure of epoxide hydrolase from Agrobacterium radiobacter AD1:an enzyme to detoxify harmful epoxides[J] . J Biol Chem,1999,274:14579-14586.
[7] Argiriadi M A,Morisseau C,Hammock B D,et al.Detoxification of environmental mutagens and carcinogens:structure,mechanism,and evolution of liver epoxide hydrolase[J] . Proc Natl Acad Sci USA,1999,96:10637-10642.
[8] Zou J,Hallberg B M,Bergfors T,et al.Structure of Aspergillus niger epoxide hydrolase at 1.8 resolution:implications for the structure and function of the mammalian microsomal class of epoxide hydrolases [J] . Structure,2000,8:111-122.
[9] Hanzlik R P,Edelman M,Michaely W J,et al.Enzymatic hydration of [18O] epoxides:role of nucleophilic mechanisms [J] . J Am Chem Soc,1976,98:1952-1955.
[10] Lacourciere G M,Armstrong R N.The catalytic mechanism of microsomal epoxide hydrolase involves an ester intermediate [J] . J Am Chem Soc,1993,115:10466-10467.
[11] Thunnissen M M G M,Nordlund P,Haeggstrom J Z.Crystal structure of human leukotriene A4 hydrolase,a bifunctional enzyme in inflammation [J] . Nat Struct Mol Biol,2001,8:131-135.
[12] Arand M,Hallberg BM,Zou J Y,et al.Stracture of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site[J].2003,22:2583-2592.
[13] Mischitz M,Faber K.Asymmetric opening of an epoxide by azide catalyzed by and immobilized enzyme preparation from Rhodococcus sp.[J] . Tetrahedron Lett,1994,35(1):81-84.
[14] Pedragosa-moreau S,Archelas A,Furstoss R.Microbiological transformations 28:enantiocomplementary epoxide hydrolyzes as a preparative access to both enantiomers of styrene oxide [J] . J Org Chem,1993,58(20):5533-5536.
[15] Elfstrom L T,Widersten M.Catalysis of potato epoxide hydrolase,StEH1 [J] . Biochem J,2005,390:633-640.
[16] Xu W,Xu J H,Pan J,et al.Enantioconvergent hydrolysis of styrene epoxides by newly discovered epoxide hydrolases in mung bean [J] . Org Lett,2006,8:1737-1740.
[17] Pedragosa-Moreau S,Morisseau C,Baratti J,et al.Microbiological transformations 37:An enantioconvergent synthesis of the beta-blocker(R)-Nifenalol using a combined chemoenzymatic approach [J] . Tetrahedron,1997,53:9707-9714.
[18] Mischitz M,Kroutil W,Wandel U,et al.Asymmetric microbial hydrolysis of epoxides[J] . Tetrahedron:Asymmetry,1995,6(6):1261-1272.
[19] Simeo Y,Faber K.Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of(+/-)-2-methylglycidyl benzyl ether [J] . Tetrahedron:Asymmetry,2006,17:402-409.
[20] Zocher F,Enzelberger M M,Bornscheuer U T,et al.Epoxide hydrolase activity of Streptomyces strains [J] . J Biotechnol,2000,77:287-292.
[21] Tang Y F,Xu J H,Ye Q,et al.Biocatalytic preparation of(S)-phenyl glycidyl ether using newly isolated Bacillus megaterium ECU1001 [J] . J Mol Catal B:Enzymatic,2001,13:61-68.
[22] Pan J,Xu J H.Marked enhancement of epoxide hydrolase production from Trichosporon loubierii ECU1040 by substrate induction and fed-batch fermentation [J] . Enzyme Microb Tech,2003,33:527-533.
[23] Li C F,Liu Q,Song X,et al.Epoxide hydrolase-catalyzed resolution of ethyl 3-phenylglycidate using whole cells of Pseudomonas sp [J] . Biotechnol Lett,2003,25:2113-2116.
[24] Liu Z,Li Y,Ping L,et al.Isolation and identification of a novel Rhodococcus sp ML-0004 producing epoxide hydrolase and optimization of enzyme production [J] . Process Biochem,2007,42:889-894.
[25] Barth S,Fischer M,Schmid R D,et al.Sequence and structure of epoxide hydrolases:A systematic analysis [J] . Proteins-Structure Function and Bioinformatics,2004,55:846-855.
[26] Liu Z Q,Li Y,Xu Y Y,et al.Cloning,sequencing,and expression of a novel epoxide hydrolase gene from Rhodococcus opacus in Escherichia coli and characterization of enzyme [J] . Appl Microbiol Biotechnol,2007,74:99-106.
[27] Lee S J,Kim H S,Kim S J,et al.Cloning,expression and enantioselective hydrolytic catalysis of a microsomal epoxide hydrolase from a marine fish,Mugil cephalus [J] . Biotechnol Lett,2007,29:237-246.
[28] Woo J H,Kang J H,Kang S,et al.Cloning and characterization of an epoxide hydrolase from Novosphingobium aromaticivorans [J] . Appl Microbiol Biotechnol,2009,82:873-881.
[29] Kotik M,Stepanek V,Maresova H,et al.Environmental DNA as a source of a novel epoxide hydrolase reacting with aliphatic terminal epoxides [J] . J Mol Catal B:Enzymatic,2009,56:288-293.
[30] Lin S J,Horsman G P,Shen B.Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster [J] . Org Lett,2010,12:3816-3819.
[31] Lin S J,Horsman G P,Chen Y H,et al.Characterization of the SgcF epoxide hydrolase supporting an(R)-vicinal diol intermediate for enediyne antitumor antibiotic C-1027 biosynthesis [J] . J Am Chem Soc,2009,131:16410-16417.
[32] Liu Z Q,Zhang L P,Cheng F,et al.Characterization of a newly synthesized epoxide hydrolase and its application in racemic resolution of(R,S)-epichlorohydrin [J] . Cata Commun,2011,16:133-139.
[33] Kumar R,Wani S I,Chauhan N S,et al.Cloning and characterization of an epoxide hydrolase from Cupriavidus metallidurans-CH34 [J] . Protein Expr Purif,2011,79:49-59.
[34] Zhao J,Chu Y Y,Li A T,et al.An unusual(R)-selective epoxide hydrolase with high activity for facile preparation of enantiopure glycidyl ethers [J] . Adv Synth Catal,2011,353:1510-1518.
[35] Smit M S,Labuschagne M.Diversity of epoxide hydrolase biocatalysts [J] . Curr Org Chem,2006,10:1145-1161.
[36] van Loo B,Spelberg J H,Kingma J,et al.Directed evolution of epoxide hydrolase from A.radiobacter toward higher enantioselectivity by error-prone PCR and DNA shuffling [J] . Chem Biol,2004,11:981-990.
[37] Reetz M T,Torre C,Eipper A,et al.Enhancing the enantioselectivity of an epoxide hydrolase by directed evolution [J] . Org Lett,2004,6:177-180.
[38] Nardini M,Rick R B,Janssen D B,et al.Structure and mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1[J] . J Mol Catal B:Enzymatic,2001,11:1035-1042.
[39] Thomaeus A,Naworyta A,Mowbray S L,et al.Removal of distal protein-water hydrogen bonds in a plant epoxide hydrolase increases catalytic turnover but decreases thermostability[J] . Protein Sci,2008,17:1275-1284.
[40] Reetz M T,Bocola M,Wang L W,et al.Directed evolution of an enantioselective epoxide hydrolase:uncovering the source of enantioselectivity at each evolutionary stage [J] . J Am Chem Soc,2009,131:7334-7343.
[41] Kotik M,Archelas A,Famerova V,et al.Laboratory evolution of an epoxide hydrolase-towards an enantioconvergent biocatalyst [J] . J Biotechnol,2011,156:1-10.
[42] Xu Y,Xu J H,Pan J,et al.Biocatalytic resolution of glycidyl aryl ethers by Trichosporon loubierii:cell/substrate ratio influences the optical purity of(R)-epoxides[J] . Biotechnol Lett,2004,26:1217-1221.
[43] Xu W,Xu J H,Pan J,et al.Enantioconvergent hydrolysis of styrene epoxides by newly discovered epoxide hydrolases in mung bean [J] . Org Lett,2006,8:1737-1740.
[44] He W H,Hua Y,Fan L Q.Isolation of total RNA and cloning of epoxide hydrolase gene from Vigna radiata [J] . Food Drug,2011,13:100-103.
[45] Jia T,Xu J,Yang S.Immobilization of Bacillus megaterium epoxide hydrolase and its catalytic performance[J] . Chin J Catal,2008,29:47-51.
[46] Ju X,Pan J,Xu J H.Enantioconvergent hydrolysis of p-nitrostyrene oxide catalyzed by mung bean epoxide hydrolase [J] . Chin J Catal,2008,29:696-700.
[47] Choi W J,Lee E Y,Yoon S J,et al.Biocatalytic production of chiral epichlorohydrin in organic solvents [J] . J Biosci Bioeng,1999,88:339-341.
[48] Baldascini H,Ganzeveld K J,Janssen D B,et al.Effect of mass transfer limitations on the enzymatic kinetic resolution of epoxides in a two-liquid-phase system [J] . Biotechnol Bioeng,2001,73:44-54.
[49] Lee E Y,Yoo S S,Kim H S,et al.Production of(S)-styrene oxide by recombinant Pichia pastoris containing epoxide hydrolase from Rhodotorula glutinis [J] . Enzyme Microb Tech,2004,35:624-631.
[50] Yeates C A,Krieg H M,Breytenbach J C.Hydroxypropyl-β-cyclodextrin induced complexation for the biocatalytic resolution of a poorly soluble epoxide [J] . Enzyme Microb Tech,2007,40:228-235.
[51] Genzel Y,Archelas A,Broxterman Q B,et al.Microbiological transformations.47.A step toward a green chemistry preparation of enantiopure(S)-2-,-3-,and -4-pyridyloxirane via an epoxide hydrolase catalyzed kinetic resolution [J] . J Org Chem,2001,66:538-543.
[52] Choi W J,Choi C Y,De Bont J A M,et al.Resolution of 1,2-epoxyhexane by Rhodotorula glutinis using a two-phase membrane bioreactor [J] . Appl Microbiol Biotechnol,1999,53:7-11.

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备注/Memo

备注/Memo:
收稿日期:2012-11-07
基金项目:国家重点基础研究发展计划(973计划)资助(2011CB710803)
作者简介:孔旭东(1987—),男,浙江萧山人,博士研究生,研究方向:环氧水解酶的结构解析和分子改造; 许建和(联系人),教授,E-mail:jianhexu@ecust.edu.cn.
更新日期/Last Update: 2013-01-30