Journal of Life Science (생명과학회지)

Korean Society of Life Science (한국생명과학회)
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Development of Asymmetric Resolution System for the Production of Chiral Styrene Oxide by Microbial Epoxide Hydrolase

미생물 유래의 Epoxide Hydrolase를 이용한 Chiral Styrene Oxide 생산용 비대칭 광학분할시스템개발

  • 이지원 (경성대학교 공과대학 식품공학과) ;
  • 윤여준 (울산대학교 공과대학 화학공학과) ;
  • 이은열 (경성대학교 공과대학 식품공학과)
  • Published : 2002.10.01
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Abstract

Asymmetric enantioselective resolution system using epoxide hydrolase activity of Aspergillus niger LK was developed and operated for the production of optically pure styrene oxide. Two-phase hollow-fiber reactor system was employed for the enhanced solubility of racemic styrene oxide in organic phase and protection of epoxide hydrolase activity in aqueous phase. For the removal of phenyl-1,2-ethandiol, the inhibitor of epoxide hydrolase, cascade hollow-fiber reactor system was also developed. Chiral (S)-styrene oxide (39 mM in dodecane) could be asymmetrically resolved with high enantiopurity (> 99% ee) using these reactor system.

Apergillus niger LK의 epoxide hydrolase 활성을 이용하여 chiral styrene oxide를 제조할 수 있는 hollow-fiber 반응기 기반의 비대칭 분할 시스템을 개발하였다. 라세믹 styrene oxide 기질을 dodecane 유기용매에 용해시켜 hollow-fiber 반응기의 lumen 부위로 공급하였으며, 생촉매인 A. niger LK 미세분말은 shell 부위로 공급함으로써 막 표면에서 비대칭 분할 반응을 수행하였다. 반응 산물로 생성되는 phenyl-1,2-ethandiol에 의한 epoxide hydrolase 활성 저해효과를 감소시키기 위하여 2번째 hollow-fiber 반응기에서 완충용액을 이용하여 diol을 추출하여 제거시켰다. 2성분 용매를 사용한 cascade형 hollow-fiber 반응기 시스템을 이용하여 광학적으로 순수한 (ee > 99%) (5)-styrene oxide를 19.5% (이론 수율 대비 39%)의 수율로 얻을 수 있었다.

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References

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