Journal of Life Science (생명과학회지)

Korean Society of Life Science (한국생명과학회)
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Biocatalysis and Biotransformation for the Production of Chiral Epoxides

바이오촉매 및 생물전환을 이용한 광학활성 에폭사이드 제조

  • Kim, Hee-Sook (Dapartment of Food Science and Technology, Kyungsung University) ;
  • Lee, Ok-Kyung (Dapartment of Food Science and Technology, Kyungsung University) ;
  • Lee, Eun-Yeol (Marine and Extreme Genome Research Center)
  • 김희숙 (경성대학교 공과대학 식품공학과) ;
  • 이옥경 (경성대학교 공과대학 식품공학과) ;
  • 이은열 (해양, 극한생물 분자유전체 연구단)
  • Published : 2005.10.01
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Abstract

Chiral epoxides are important chiral synthons in organic synthesis for the production of chiral pharmaceuticals and functional food additives. Chiral epoxides can be synthesized by enantioselective introduction of oxygen to double bond of substrate by monooxygenase. Peroxidase also carry out asymmetric epoxidation of alkene in the presence of hydrogen peroxide. Kinetic resolution of racemic epoxides via enantioselective hydrolysis reaction by epoxide hydrolase (EH) is a very promising method since chiral epoxides with a high optical purity can be obtained from cheap and readily available racemic epoxides. In this review, various biocatalytic approaches for the production of chiral epoxides with several examples are presented and their commercial potential is discussed.

광학활성 에폭사이드는 광학활성 의약품, 기능성 식품 제조용 광학활성 중간체로 사용될 수 있다. 바이오촉매를 이용하여 광학활성 에폭사이드를 제조하는 방법으로는, mono-oxygenase나 peroxidase 등을 이용하여 알켄 기질의 이중결합을 비대칭 에폭시화반응을 통해 제조하는 방법이 있다. Kinetic resolution을 이용하는 방법으로는 epoxide hydrolase를 이용하여 특정 이성질체만을 diol로 가수분해하여 제거시켜 광학활성 에폭사이드를 얻는 방법 등이 있다. 다양한 생물전환 기술, directed evolution 및 site-specific muta-genesis 등을 이용한 광학활성 에폭사이드 제조용 바이오촉매개량 기술 등 효율적인 광학활성 에폭사이드 제조 시스템에 대한 연구 개발도 활발히 진행되고 있어 향후에 상업화가 가능할 것으로 기대된다.

Keywords

References

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