Abstract
Chiral epoxides are useful chiral synthons in organic synthesis, and various biological methods have been investigated for their production. In this work, the enantioselective resolution of racemic styrene oxide was investigated using Aspergillus niger sp. for the production of optically pure (S)-styrene oxide. The enantioselectivity and initial hydrolysis rates of the racemic substrate were highly dependent of the pH, temperature, and the volume ratio of cosolvent. Experimental sets of pH, temperature, and the volume ratio of cosolvent were investigated using a central composite experimental design, and reaction conditions were optimized by response surface analysis. The optimal conditions of pH, temperature, and the volume ratio of cosolvent were determined to be 7.78, $28.32^{\circ}C$, and 2.4%(v/v), respectively, and optically pure (S)-styrene oxide (>99% ee) was obtained at 35% yield using this microbial enantioselective hydrolysis reaction.
에폭사이드 가수분해효소 활성이 우수한 Aspergillus niger 를 생촉매로 이용하여 업체선택적 가수분해 반응을 통해 라세믹 styrene oxide 기질로부터 광학활성 (S)-styrene oxide를 생산하는 실험을 수행하였다. (R)-styrene oxide 이성질체에 대한 초기 가수분해 속도에 영향을 주는 실험인자들인 pH, 반응온도, cosolvent 첨가량 등에 대해 중심합성계획법을 이용한 반응표면 분석을 통해 가수분해반응 속도를 향상시킬 수 있는 최적 반응조건을 결정하였다. pH 7.78, 반응온도 2 $28.32^{\circ}C$ 및 cosolvent 첨가량 2.4% (v/v)의 조건에서 약 10시간 정도의 반응을 통해 ee 값이 100%인 광학적으로 순수한 (S)-styrene oxide를 35% 정도(이론수율 = 50%)의 높은 수율로 얻을 수 있었다.
