Itoh Toshiyuki, Matsushita Yuichi, Abe Yoshikazu, Han Shi-Hui, Wada Shohei, Hayase Shuichi, Kawatsura Motoi, Takai Shigeomi, Morimoto Minoru, Hirose Yoshihiko
Department of Materials Sciences, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan.
Chemistry. 2006 Dec 13;12(36):9228-37. doi: 10.1002/chem.200601043.
Several types of imidazolium salt ionic liquids were prepared derived from poly(oxyethylene)alkyl sulfate and used as an additive or coating material for lipase-catalyzed transesterification in an organic solvent. A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phenylethanol by using vinyl acetate in diisopropyl ether or a hexane solvent system. In particular, a remarkable acceleration was accomplished by the ionic liquid coating with lipase PS in an iPr(2)O solvent system while maintaining excellent enantioselectivity; it reached approximately 500- to 1000-fold acceleration for some substrates with excellent enantioselectivity. A similar acceleration was also observed for IL 1-coated Candida rugosa lipase. MALDI-TOF mass spectrometry experiments of the ionic-liquid-coated lipase PS suggest that ionic liquid binds with lipase protein.
制备了几种由聚（氧乙烯）烷基硫酸盐衍生而来的咪唑鎓盐离子液体，并将其用作有机溶剂中脂肪酶催化酯交换反应的添加剂或涂层材料。在洋葱伯克霍尔德菌脂肪酶（脂肪酶PS-C）催化1-苯乙醇与乙酸乙烯酯在二异丙醚或己烷溶剂体系中的酯交换反应中，当盐相对于底物以3-10 mol%添加时，对映选择性显著提高。特别是，在异丙醚溶剂体系中，用离子液体包覆脂肪酶PS可实现显著的加速，同时保持优异的对映选择性；对于一些底物，对映选择性优异时，加速倍数达到约500至1000倍。对于IL 1包覆的皱褶假丝酵母脂肪酶也观察到了类似的加速。离子液体包覆脂肪酶PS的基质辅助激光解吸电离飞行时间质谱实验表明，离子液体与脂肪酶蛋白结合。
