Epoxide Hydrolases: Multipotential Biocatalysts

被引:22
作者
Bucko, Marek [1 ]
Kaniakova, Katarina [2 ]
Hronska, Helena [2 ]
Gemeiner, Peter [1 ]
Rosenberg, Michal [2 ]
机构
[1] Slovak Acad Sci, Inst Chem, Ctr Glycom, Dept Glycobiotechnol, Dubravska Cesta 9, Bratislava 84538, Slovakia
[2] Slovak Univ Technol Bratislava, Inst Biotechnol, Fac Chem & Food Technol, Radlinskeho 9, Bratislava 81237, Slovakia
关键词
epoxide hydrolase; epoxides; chiral precursors; biocatalysis; enantioselectivity; enzyme engineering; stabilization; immobilization; enzyme cascade; AGROBACTERIUM-RADIOBACTER AD1; HYDROLYTIC KINETIC RESOLUTION; CIS-EPOXYSUCCINATE HYDROLASE; RACEMIC STYRENE OXIDE; DIRECTED EVOLUTION; MICROBIOLOGICAL TRANSFORMATIONS; CASCADE BIOCATALYSIS; ASPERGILLUS-NIGER; ENZYMATIC TRANSFORMATIONS; ASYMMETRIC HYDROLYSIS;
D O I
10.3390/ijms24087334
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Epoxide hydrolases are attractive and industrially important biocatalysts. They can catalyze the enantioselective hydrolysis of epoxides to the corresponding diols as chiral building blocks for bioactive compounds and drugs. In this review article, we discuss the state of the art and development potential of epoxide hydrolases as biocatalysts based on the most recent approaches and techniques. The review covers new approaches to discover epoxide hydrolases using genome mining and enzyme metagenomics, as well as improving enzyme activity, enantioselectivity, enantioconvergence, and thermostability by directed evolution and a rational design. Further improvements in operational and storage stabilization, reusability, pH stabilization, and thermal stabilization by immobilization techniques are discussed in this study. New possibilities for expanding the synthetic capabilities of epoxide hydrolases by their involvement in non-natural enzyme cascade reactions are described.
引用
收藏
页数:27
相关论文
共 164 条
[71]   Preparing β-blocker (R)-Nifenalol based on enantioconvergent synthesis of (R)-p-nitrophenylglycols in continuous packed bed reactor with epoxide hydrolase [J].
Li, Fu-Long ;
Zheng, Yu-Cong ;
Li, Hao ;
Chen, Fei-Fei ;
Yu, Hui-Lei ;
Xu, Jian-He .
TETRAHEDRON, 2019, 75 (12) :1706-1710
[72]   Regioselectivity Engineering of Epoxide Hydrolase: Near-Perfect Enantioconvergence through a Single Site Mutation [J].
Li, Fu-Long ;
Kong, Xu-Dong ;
Chen, Qi ;
Zheng, Yu-Cong ;
Xu, Qin ;
Chen, Fei-Fei ;
Fan, Li-Qiang ;
Lin, Guo-Qiang ;
Zhou, Jiahai ;
Yu, Hui-Lei ;
Xu, Jian-He .
ACS CATALYSIS, 2018, 8 (09) :8314-8317
[73]   Machine Learning Enables Selection of Epistatic Enzyme Mutants for Stability Against Unfolding and Detrimental Aggregation [J].
Li, Guangyue ;
Qin, Youcai ;
Fontaine, Nicolas T. ;
Ng Fuk Chong, Matthieu ;
Maria-Solano, Miguel A. ;
Feixas, Ferran ;
Cadet, Xavier F. ;
Pandjaitan, Rudy ;
Garcia-Borras, Marc ;
Cadet, Frederic ;
Reetz, Manfred T. .
CHEMBIOCHEM, 2021, 22 (05) :904-914
[74]   Multiparameter Optimization in Directed Evolution: Engineering Thermostability, Enantioselectivity, and Activity of an Epoxide Hydrolase [J].
Li, Guangyue ;
Zhang, Hui ;
Sun, Zhoutong ;
Liu, Xinqi ;
Reetz, Manfred T. .
ACS CATALYSIS, 2016, 6 (06) :3679-3687
[75]   Using multiple site-directed modification of epoxide hydrolase to significantly improve its enantioselectivity in hydrolysis of rac-glycidyl phenyl ether [J].
Li, Yao ;
Ou, Xiaoyang ;
Guo, Zewang ;
Zong, Minhua ;
Lou, Wenyong .
CHINESE JOURNAL OF CHEMICAL ENGINEERING, 2020, 28 (08) :2181-2189
[76]   Biocatalysis as an alternative for the production of chiral epoxides: A comparative review [J].
Lin, Hui ;
Liu, Jing-Yuan ;
Wang, Hai-Bo ;
Ahmed, Abeer Ahmed Qaed ;
Wu, Zhong-Liu .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2011, 72 (3-4) :77-89
[77]  
Ling XQ, 2011, AFR J BIOTECHNOL, V10, P3436
[78]   Designing of a Cofactor Self-Sufficient Whole-Cell Biocatalyst System for Production of 1,2-Amino Alcohols from Epoxides [J].
Liu, Song ;
Zhang, Xian ;
Liu, Fei ;
Xu, Meijuan ;
Yang, Taowei ;
Long, Mengfei ;
Zhou, Junping ;
Osire, Tolbert ;
Yang, Shangtian ;
Rao, Zhiming .
ACS SYNTHETIC BIOLOGY, 2019, 8 (04) :734-743
[79]   Remarkable improvement in the regiocomplementarity of a Glycine max epoxide hydrolase by reshaping its substrate-binding pocket for the enantioconvergent preparation of (R)-hexane-1,2-diol [J].
Liu, You-Yi ;
Wu, Meng-Di ;
Zhu, Xiu-Xiu ;
Zhang, Xia-Ding ;
Zhang, Chen ;
Xu, Yao-Hui ;
Wu, Min-Chen .
MOLECULAR CATALYSIS, 2021, 514
[80]   Microbiological transformations. Part 45: A green chemistry preparative scale synthesis of enantiopure building blocks of Eliprodil: elaboration of a high substrate concentration epoxide hydrolase-catalyzed hydrolytic kinetic resolution process [J].
Manoj, KM ;
Archelas, A ;
Baratti, J ;
Furstoss, R .
TETRAHEDRON, 2001, 57 (04) :695-701