溶剂和酰基受体对α-氰基-3-苯氧基苄醇乙酯的酶促对映体选择性转酯化反应的影响  

Effects of Solvents and Acyl acceptors on the Lipase-Catalyzed Enantioselective Transesterification of α-Cyano-3-Phenoxybenzyl Acetate

作　　者：罗积杏[1] 齐楠[2] 唐世平[3] 杨立荣[3] 

机构地区：[1]上海市农药研究所,上海200032 [2]安捷伦科技上海有限公司,上海200020 [3]浙江大学生物工程研究所,浙江杭州310027

出　　处：《分子催化》2005年第5期394-398,共5页Journal of Molecular Catalysis(China)

摘　　要：研究了在有机溶剂中固定化Alcaligenessp.脂肪酶催化α-氰基-3-苯氧基苄醇乙酯的对映体选择性转酯化反应,考察了不同性质的溶剂和酰基受体对酶的催化活性和选择性以及对产物稳定性的影响.结果发现在弱极性溶剂如正己烷中酶具有较高的催化活性但产物e.e.%值低,而且容易分解;在四氢呋喃等溶剂中酶催化活性相对低,但产物e.e.%值高,也较为稳定;但反应时间太长,会导致产物分解及纯度下降;不同酰基受体对酶反应无显著影响,甲醇为最佳酰基受体,太多醇会导致反应速率下降;溶剂水含量大于2.0%时对酶活性和产物稳定性产生明显不利影响.在优化条件下,酶反应可得到(S)-α-氰基-3-苯氧基苄醇产率>48%,纯度>99%e.e.The immobilized Alcaligenes sp. lipase-catalyzed enantioselective transesterification of α-eyano-3-phenoxybenzyl acetate in organic media was studied. The effects of solvent and acyl acceptors on the stability of the product, and the catalytic activity and enantioselectivity of the lipase were investigated. The experimental results indicated that lipase showed high activity in hydrophilic solvents such as Hexane, but had low enantioselectivity, and the decomposition of cyanohydrin was remarkable in those kinds of solvents. When the reaction performed in THF, the highest enantioselectivity was obtained, but the decomposition of cyanohydrin was observed yet, and the enantiomeric excess of product decreased with the reaction time prolonged; No marked effects of different acyl acceptors on the reaction was observed, methanol was the best choice, too many alcohol will reduce the reaction rate; when the content of water in THF 〉 2%, disadvantage influence on the enzyme activity and the product stability appeared. Under optimal condition the reaction would give a 〉 48% yield of（S）-α-cyano-3-phenoxybenzyl alcohol with 〉 99e.e. %.

关 键 词：α-氰基-3-苯氧基苄醇乙酯 对映体选择性转酯化 脂肪酶 有机溶剂 酰基受体 

分 类 号：O643.32[理学—物理化学]