Design of phosphonium ionic liquids for lipase-catalyzed transesterification

被引:66
作者
Abe, Yoshikazu [1 ]
Kude, Keisuke [1 ]
Hayase, Shuichi [1 ]
Kawatsura, Motoi [1 ]
Tsunashima, Katsuhiko [2 ]
Itoh, Toshiyuki [1 ]
机构
[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan
[2] Nippon Chem Ind Co Ltd, Koto Ku, Tokyo 1368515, Japan
关键词
ionic liquid; phosphonium salt; lipase; transesterification; rapid reaction;
D O I
10.1016/j.molcatb.2007.11.010
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Ionic liquids are now recognized as solvents for use in lipase-catalyzed reactions; however, there still remains a serious drawback in that the rate of reaction in an ionic liquid is slower than that in a conventional organic solvent. To overcome this problem, attempts have been made to evolve phosphonium ionic liquids appropriate for lipase-catalyzed reaction; several types of phosphonium salts have been prepared and their capability evaluated for use as solvent for the lipase-catalyzed reaction. Very rapid lipase PS-catalyzed transesterification of secondary alcohols was obtained when 2-methoxyethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)imide ([MEBu3P][NTf2]) was used as solvent, affording the first example of a reaction rate superior to that in diisopropyl ether. (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:81 / 85
页数:5
相关论文
共 32 条
[1]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[2]   Application of hydrophilic ionic liquids as co-solvents in chloroperoxidase catalyzed oxidations [J].
Chiappe, Cinzia ;
Neri, Lisa ;
Pieraccini, Daniela .
TETRAHEDRON LETTERS, 2006, 47 (29) :5089-5093
[3]   Reactivity of ionic liquids [J].
Chowdhury, Shahana ;
Mohan, Ram S. ;
Scott, Janet L. .
TETRAHEDRON, 2007, 63 (11) :2363-2389
[4]   Understanding structure -: Stability relationships of Candida antartica lipase B in ionic liquids [J].
De Diego, T ;
Lozano, P ;
Gmouh, S ;
Vaultier, M ;
Iborra, JL .
BIOMACROMOLECULES, 2005, 6 (03) :1457-1464
[5]   Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol [J].
Ghanem, A ;
Schurig, V .
TETRAHEDRON-ASYMMETRY, 2003, 14 (01) :57-62
[6]   Enhanced enantioselectivity and remarkable acceleration on the lipase-catalyzed transesterification using novel ionic liquids [J].
Itoh, T ;
Han, SH ;
Matsushita, Y ;
Hayase, S .
GREEN CHEMISTRY, 2004, 6 (09) :437-439
[7]   Novel supporting materials of lipase PS suitable for use in an ionic liquid solvent system [J].
Itoh, T ;
Ouchi, N ;
Nishimura, Y ;
Hui, HS ;
Katada, N ;
Niwa, M ;
Onaka, M .
GREEN CHEMISTRY, 2003, 5 (05) :494-496
[8]  
Itoh T, 2003, ACS SYM SER, V856, P251
[9]   1-butyl-2,3-dimethylimidazolium tetrafluoroborate: the most desirable ionic liquid solvent for recycling use of enzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor [J].
Itoh, T ;
Nishimura, Y ;
Ouchi, N ;
Hayase, S .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 26 (1-2) :41-45
[10]   Lipase-catalyzed enantioselective acylation in a halogen free ionic liquid solvent system [J].
Itoh, T ;
Ouchi, N ;
Hayase, S ;
Nishimura, Y .
CHEMISTRY LETTERS, 2003, 32 (07) :654-655