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KMID : 0380020070220030123
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Korean Journal of Biotechnology and Bioengineering
2007 Volume.22 No. 3 p.123 ~ p.128
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Enantioconvergent Hydrolysis of Racemic Epoxides for Production of Enantiopure Epoxides and Vicinal Diols using Epoxide Hydrolases
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Lee Eun-Yeol
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Abstract
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One drawback of conventional kinetic resolution of racemic epoxides by epoxide hydrolase (EH) is that the theoretical yield can never exceed 50%. This 50% limitation can be overcome by using enantioconvergent process, in which both enantiomers of the racemic epoxide are transformed via stereochemically matching pathways into a single enantiopure diol as the sole product in 100% theoretical yield. In order to make a single enantiopure vicinal diol, the two enantiomers of the racemic epoxide must be hydrolyzed with retention and inversion of configuration each other. The EHs should be enantio- and regiospecific at the same time. The enantioconvergent hydrolysis with EHs and relevant biotransformation for preparing enantiopure epoxides and vicinal diols with a high yield are reviewed.
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KEYWORD
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Enantioconvergent hydrolysis, enantioselectivity, epoxide hydrolase, enantiopure vicinal diol, regioselectivity
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