Journal of Life Science (생명과학회지)

Korean Society of Life Science (한국생명과학회)
권호 표지
DOI QR코드

DOI QR Code

Optimization of Epoxide Hydrolase-Catalyzed Enantioselective Hydrolysis of Racemic Styrene Oxide

Rhodotorula sp. CL-83 유래의 에폭사이드 가수분해효소를 이용한 라세믹 Styrene Oxide 입체특이성 가수분해 조건 최적화

  • 이은열 (경성대학교 공과대학 식품공학과)
  • Published : 2002.12.01
Download PDF
⟨ Previous Next ⟩

Abstract

Enantioselective hydrolysis of racemic styrene oxide by Rhodotorula sp. CL-82 was investigated. Reaction conditions including pH, temperature, and volume ratio of organic cosolvent were optimized using response surface methodology, and the optimal conditions of pH, temperature, and the volume ratio of cosolvent were determined to be 7.64, $33.26^{\circ}C$, and 3.09 %(v/v), respectively. Chiral (S)-phenyl oxirane could be obtained with high enantiomeric purity (ee ＞ 99%) and 20% yield (theoretical yield ＝ 50%) at the optimal rendition.

Rhodotorula sp. CL-82 유래 의 epoxide hydrolase 활성을 이용하여 라세믹 styrene oxide에 대한 입체선택적 가수분해 반응을 실시하였다. Rhodotorula sp. CL-82 생촉매의 입체선택적 가수분해속도를 나타내주는 반응표면 곡선에 대한 분석을 통해 pH, 반응주도, cosolvent 첨가량에 대한 최적조건을 각각 7.6,$33.3^{\circ}C$ , 3%(v/v)으로 결정하였다. 최적반응조건에서 약 4시간 정도의 반응을 통해 ee값이 99% 이상인 광학적으로 순수한 (S)-styrene oxide를 이론 수율대비 40% 수율로 얻을 수 있었다.

Keywords

References

  1. Current Opinion in Chem. Biology v.5 Synthetic applications of epoxide hydrolases Archelas, A.;R. Furstoss https://doi.org/10.1016/S1367-5931(00)00179-4
  2. Tetrahedron v.50 Chemical and biological synthesis of chiral epoxides Besse, P.;H. Veschambre https://doi.org/10.1016/S0040-4020(01)85362-X
  3. Biotechnol. Techniques v.12 Kinetic resolution for optically active epoxides by microbial enantioselective hydrolysis Choi, W. J.;E. C. Huh;H. J. Park;E. Y. Lee;C. Y. Choi https://doi.org/10.1023/A:1008825508904
  4. J. Biosci. Bioeng. v.88 Biocatalytic production of chiral epichlorohydrin in organic solvent Choi, W. J.;E. Y. Lee;S. J. Yoon;C. Y. Choi https://doi.org/10.1016/S1389-1723(00)80022-5
  5. Kor. J. Biotechnol. Bioeng. v.17 Epoxide hydrolase-catalyzed hydrolytic kinetic resolution for the production of chiral epoxides Lee, E. Y
  6. Current Opinion in Biotechnol. v.12 Microbial epoxide hydrolases for preparative biotransformatins Steinreiber, A.;K. Faber https://doi.org/10.1016/S0958-1669(01)00262-2
  7. Tetrahedron: Asymmetry v.8 Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides by Rhodotorula glutinis Weijers, C. A. G. M. https://doi.org/10.1016/S0957-4166(97)00012-8
  8. Kor. J. Biotechnol. Bioeng. v.15 Production of chiral styrene oxide by microbial enantioselective hydrolysis reaction Yoon, S. J.;E. Y. Lee