Molecular engineering of epoxide hydrolase and its application to asymmetric and enantioconvergent hydrolysis.
Safety and regulatory issues favor increasing use of enantiopure compounds in pharmaceuticals. Enantiopure epoxides and diols are valuable intermediates in organic synthesis for the production of optically active pharmaceuticals. Enantiopure epoxide can be prepared using epoxide hydrolase (EH)-catalyzed asymmetric hydrolysis of its racemate. Enantioconvergent hydrolysis of racemic epoxides by EHs possessing complementary enantioselectivity and regioselectivity can lead to the formation of enantiopure vicinal diols with high yield. EHs are cofactor-independent and easy-to-use catalysts. EHs will attract much attention as commercial biocatalysts for the preparation of enantiopure epoxides and diols. In this paper, recent progress in molecular engineering of EHs is reviewed. Some examples and prospects of asymmetric and enantioconvergent hydrolysis reactions are discussed as supplements to molecular engineering to improve EH performance.
Lee
Eun Yeol
EY
Department of Food Science and Biotechnology, Kyungsung University, Daeyeon-dong, Nam-gu, Busan 608-736, Republic of Korea. eylee@ks.ac.kr
Shuler
Michael L
ML
D004800:Enzymes, Immobilized / Q000378:metabolism; D004851:Epoxide Hydrolases / Q000737:chemistry / Q000502:physiology*; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D006868:Hydrolysis; D015202:Protein Engineering / Q000379:methods*; D017386:Sequence Homology, Amino Acid; D013329:Structure-Activity Relationship
D004800:Enzymes, Immobilized; D004852:Epoxy Compounds; D004851:Epoxide Hydrolases