(I) 本文提出一個分析解，探討以酵素為觸媒進行不可逆醯基轉化動態動力分割系統中副反應對目標對掌性異構物產量及光學純度之影響。此外，以脂肪酵素進行(R, S)-naproxen 2,2,2-trifluoroethyl thioester與4-morpholine ethanol之轉硫酯化動態動力分割為範例，進一步比較理論預測與實驗結果間差異。在控制異辛烷溶液中之初始水含量為0.113下，發現添加消旋觸媒三辛基胺對酵素水解副反應、酵素對醇與水之選擇性有重大影響。理論分析顯示若酵素對水解及酯化副反應有較好之反應性與立體選擇性時，副反應將有助於增加目標對掌性異構物產量及光學純度，此結果特別適合於消旋速率較快之反應系統。
　　(II) 本文以木瓜脂肪進行氯基苯氧基丙酸之酯化分割，比文獻中表現最好的C. rugosa lipase，擁有更佳的鏡像選擇性及反應性，且最佳反應溫度超過60度以上，再加上其為天然固定化的性質、酵素容易回收再使用、在價錢上較商業化C. rugosa lipase便宜，這顯示木瓜脂肪是具有競爭力的生化觸媒。總而言之，在所選擇的反應條件下，利用木瓜脂肪進行氯基苯氧基丙酸的酵素製程已成功地被開發。
　　動力學數據顯示酸與醇皆顯示基質抑制作用，然而在高濃度醇下，酵素的鏡像選擇性最高可提升至20倍以上，顯示三甲基矽甲醇的濃度改變可視為一有效改善酵素鏡像選擇性的策略。而熱力學分析顯示木瓜脂肪催化不同溶劑下不同氯取代基位置的氯基苯氧基丙酸，皆遵循焓熵補償效應。與lipase MY比較可發現，木瓜脂肪與鄰鄰–氯基苯氧基丙酸上的氯有一作用力存在，導致兩種酵素在面對鄰位氯取代的酸基質時有截然不同的鏡像選擇性。

　(I) An analytical solution for the dynamic kinetic resolution of enzyme-catalyzed irreversible acyl transfer was employed to study the side-reaction effects on the yield and optical purity of the desired enantiomeric product. A lipase-catalyzed enantioselective thiotransesterification between (R, S)-naproxen 2,2,2-trifluoroethyl thioester and 4-morpholine ethanol with in situ racemization of (R)-thioester using trioctylamine as the racemization catalyst in isooctane was designed as a model system to compare the theoretical predictions. Under an initial water activity of 0.113, adding trioctylamine was found to have profound effects on the hydrolysis side-reactions, thus enhancing the chemoselectivity of the lipase to the alcohol in comparison with water. Theoretical analysis also indicated that the time-course yield and the enantiomeric excess for the desired enantiomer could be improved if the employed lipase had higher activity and enantioselectivity for the hydrolysis and esterification side-reactions, especially when the base had a similar racemization rate compared with the rate of the fast-reaction substrate.
　(II) A partially purified Carica papaya (pCPL) was explored as an effective biocatalyst for the esterification resolution of various (RS)-2-chlorophenoxypropionic acids (CPP) with trimethylsilylmethanol in anhydrous isooctane. In comparison with the performance of crude Candida rugosa lipase, pCPL has high E value (> 100) for 2-chloro and 4-chloro but not 3-chloro substituted CPP. More than an order-of-magnitude lower reactivity was obtained for the hindered substrate of (RS)-2-(2-chlorophenoxy)propionic acid. The thermodynamic analysis indicates that the enantiomeric discrimination for all reaction systems is mainly driven by the difference of activation enthalpy. A good enthalpy-entropy compensation effect between -ΔΔH and -ΔΔS is demonstrated and elucidated for the region-effect of substrates containing 2-, 3- or 4-chloro substituent. The kinetic analysis indicates that pCPL is inhibited strongly by the acid substrate, but to a less extent by the alcohol substrate. However with the penalty of decreasing pCPL activity, the E value in isooctane can be greatly enhanced when trimethylsilylmethanol concentration higher than 40 mM is employed.

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