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Increased Enantioselectivity and Remarkable Acceleration of Lipase‐Catalyzed Transesterification by Using an Imidazolium PEG–Alkyl Sulfate Ionic Liquid
Author(s) -
Itoh Toshiyuki,
Matsushita Yuichi,
Abe Yoshikazu,
Han Shihui,
Wada Shohei,
Hayase Shuichi,
Kawatsura Motoi,
Takai Shigeomi,
Morimoto Minoru,
Hirose Yoshihiko
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601043
Subject(s) - lipase , transesterification , ionic liquid , chemistry , candida rugosa , alkyl , diisopropyl ether , organic chemistry , solvent , catalysis , enzyme
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 i Pr 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.