KSBB Journal

The Korean Society for Biotechnology and Bioengineering (한국생물공학회)
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Enantioconvergent Hydrolysis of Racemic Epoxides for Production of Enantiopure Epoxides and Vicinal Diols using Epoxide Hydrolases

에폭사이드 가수분해효소에 의한 광학수렴반응을 이용한 광학활성 에폭사이드 및 Vicinal Diol 제조

  • Lee, Eun-Yeol (Department of Food Science and Biotechnology, Kyungsung University)
  • 이은열 (경성대학교 공과대학 식품생명공학과)
  • Published : 2007.06.30
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Abstract

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.

에폭사이드 가수분해 효소를 이용하여 라세믹 에폭사이드 기질로부터 광학활성 에폭사이드 또는 vic-diol을 제조하는 동력학적 분할법은 이론 수율이 50%로 제한된다는 단점이 있다. 이러한 문제점을 해결하기 위하여 이론 수율 100%를 얻을 수 있는 다양한 생물전환 방법들이 최근에 개발되고 있다. 서로 상보적인 입체 및 위치특이성을 가진 에폭사이드 가수분해효소에 의한 광학수렴반응을 이용한 광학활성 vic-diol 제조법, 에폭사이드 가수분해효소가 촉발하는 cascade 반응을 통해 라세믹 haloalkyl 에폭사이드로부터 광학활성 epoxy alcohol 또는 THF를 제조하는 방법, ADH를 이용하여 haloketone을 환원시킨 다음 자발적인 cyclization 반응을 통해 광학활성 에폭사이드를 제조하는 방법들이 개발되었다. 이러한 방법들은 높은 광학순도를 가진 광학활성 물질들을 이론수율 100%로 제조할 수 있으므로 향후에 상업화 사례가 많아질 것으로 기대된다.

Keywords

References

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