Abstract
Batch production of (S)-phenyl oxirane was investigated using epoxide hydrolase activity of Rhodosporidium toruloides SJ-4. Effect of reaction condition of asymmetric biohydrolysis of racemic phenyl oxirane was analyzed and optimized by response surface methodology. The optimal conditions of pH, temperature and DMSO cosolvent ratio were 7.4, $34^P\circ}C$, and 2.3%(v/v), respectively. The final yield was enhanced up to 67%, and reaction times required to reach 99% ee (enatiomeric excess) decreased down to 50% by response surface methodology Enantiopure (S)-phenyl oxirane with 100% enantiopurity and 24% yield (theoretical yield = 50%) was obtained from racemic substrate.
라세믹 phenyl oxirane 기질에 대한 asymmetric biohydrolysis 활성이 우수한 Rhodosporidium toruloides SJ-4를 생촉매로 이용하여 입체선택적 가수분해 반응을 통해 라세믹 phenyl oxirane 기질로부터 광학활성 (S)-phenyl oxirane를 회분식으로 생산하는 실험을 수행하였다. (R)-phenyl oxirane 이성질체에 대한 초기 가수분해 속도에 영향을 주는 실험인자들인 pH, 반응온도, DMSO cosolvent 첨가량 등에 대해 중심합성계획법을 이용한 반응표면 분석을 통해 가수분해반응 속도를 향상시킬 수 있는 최적 반응조건을 결정하였다. pH 7.4, 반응온도 34℃ 및 DMSO 첨가량 2.3%(v/v)의 조건에서 라세믹 기질 초기 농도 100mM로부터 약 10시간 정도의 반응을 통해 ee 값이 100%인 광학적으로 순수한 (S)-phenyl oxirane를 24% 정도 (이론수율 = 50%)의 높은 수율로 얻을 수 있었다. ^u Batch production of (S)-phenyl oxirane was investigated using epoxide hydrolase activity of Rhodosporidium toruloides SJ-4. Effect of reaction condition of asymmetric biohydrolysis of racemic phenyl oxirane was analyzed and optimized by response surface methodology. The optimal conditions of pH, temperature and DMSO cosolvent ratio were 7.4, 34 ℃, and 2.3%(v/v), respectively. The final yield was enhanced up to 67%, and reaction times required to reach 99% ee (enatiomeric excess) decreased down to 50% by response surface methodology Enantiopure (S)-phenyl oxirane with 100% enantiopurity and 24% yield (theoretical yield = 50%) was obtained from racemic substrate.
