臺灣博碩士論文加值系統

本文除了自外消旋Suprofen合成2,2,2-trifluoroethyl α-methyl-
p-(2-thenoyl) phenylacetate（三氟酯）以克服Suprofen在環己烷中低
溶解度的困難外，並利用各種脂肪酵素催化三氟酯與4-(2-hygroxyethyl)
morpholine的酯化反應篩選出具有最佳(S)-型鏡像選擇性的Candida
rugosa 脂肪酵素。再藉由此一脂肪酵素進行光學分割不同的胺基醇和雙
醇類與2,2,2-trifluoroethyl α-methyl-p-(2-thenoyl)phenylacetate
反應，發現在胺基醇類中4-(2-hydroxyethyl)morpholine、3-
diethylamino-1-propanol、1-diethylamino-2-propanol和1-
dimethylamino-2-propanol 以及雙醇類的di(ethylene glycol) 、tri(
ethylene glycol) 和tetra(ethylene glycol)皆有不錯的鏡像比值。
文中並探討醇濃度變化對反應性的影響、雙醇類及胺基醇為醯基受體時轉
酯速率與 水解速率之變化、酵素經冷凍乾燥後其催化能力受酵素水含量
的影響以及轉酯產的分離。

The problem of low Suprofen solubility in the production of
the desired (S)-Suprofen ester prodrug in cyclohexane can be
solved by using the more soluble2,2,2-trifluoroethyl alpha-
methyl-p-(2-thenoyl)phenylacetate as the substrate.In the
enantioselective transesterification reaction of
2,2,2-trifluoroethyl alpha-methyl-p-(2-thenoyl)phenylacetate
with 4-(2-hydroxyethyl)morpholine catalyzed by various
lipases, Candida rugosa lipase has the best enantiomeric ratio.
With lipase as the biocatalyst by employing various alcohols
containg amine group or poly(ethylene glycol)s as the acyl
acceptor, we have found that4-(2-hydroxyethyl)morpholine,
3-diethylamino-1-propanol, 1-diethylamino-2- propanol,
1-dimethylamino-2-propanol, di(ethylene glycol), tri(ethylene
glycol) and tetra(ethylene glycol) possess good reactivity and
enantiomeric ratio. Results and discussing on the effects
of alcohol concentration and watercontent in the lyophilized
enzyme on the lipase reactivity, as well as the production
separation by extraction were also reported.