Efficient lipase-catalyzed enantioselective acylation under reduced pressure conditions in an ionic liquid solvent system

被引:68
作者
Itoh, T [1 ]
Akasaki, E
Nishimura, Y
机构
[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan
[2] Okayama Univ, Fac Educ, Dept Chem, Okayama 7008530, Japan
关键词
D O I
10.1246/cl.2002.154
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lipase-catalyzed transesterification was demonstrated using methyl esters as acyl donors under reduced pressure in an ionic liquid ([bmim]PF6) solvent system. The transesterification of 5-phenyl-1-penten-3-ol took place smoothly under reduced pressure at 27 hPa at 40 degreesC when methyl phenylthioacetate was used as acyl donor in [bmim]PF6, and we succeeded in obtaining the corresponding acylated compound in optically pure form; this makes it possible to use lipase repeatedly because there was no drop in the reaction rate despite three repetitions of the process.
引用
收藏
页码:154 / 155
页数:2
相关论文
共 16 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]   A highly chemo- and stereoselective synthesis of β-keto esters via a polymer-supported lipase catalyzed transesterfication [J].
Córdova, A ;
Janda, KD .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1906-1909
[3]  
Cull SG, 2000, BIOTECHNOL BIOENG, V69, P227
[4]   Enzymatic catalysis of formation of Z-aspartame in ionic liquid -: An alternative to enzymatic catalysis in organic solvents [J].
Erbeldinger, M ;
Mesiano, AJ ;
Russell, AJ .
BIOTECHNOLOGY PROGRESS, 2000, 16 (06) :1129-1131
[5]   THE GENERATION OF GLYCERYL ETHER LIPIDS HIGHLY ENRICHED WITH EICOSAPENTAENOIC ACID AND DOCOSAHEXAENOIC ACID BY LIPASE [J].
HARALDSSON, GG ;
THORARENSEN, A .
TETRAHEDRON LETTERS, 1994, 35 (41) :7681-7684
[6]   THE PREPARATION OF HOMOGENEOUS TRIGLYCERIDES OF EICOSAPENTAENOIC ACID AND DOCOSAHEXAENOIC ACID BY LIPASE [J].
HARALDSSON, GG ;
GUDMUNDSSON, BO ;
ALMARSSON, O .
TETRAHEDRON LETTERS, 1993, 34 (36) :5791-5794
[7]   Immobilized baker's yeast reduction of ketones in an ionic liquid, [bmim]PF6 and water mix [J].
Howarth, J ;
James, P ;
Dai, JF .
TETRAHEDRON LETTERS, 2001, 42 (42) :7517-7519
[8]   Lipase-catalyzed enantioselective acylation in the ionic liquid solvent system: Reaction of enzyme anchored to the solvent [J].
Itoh, T ;
Akasaki, E ;
Kudo, K ;
Shirakami, S .
CHEMISTRY LETTERS, 2001, (03) :262-263
[9]   ENHANCED ENANTIOSELECTIVITY OF AN ENZYMATIC-REACTION BY THE SULFUR FUNCTIONAL-GROUP - A SIMPLE PREPARATION OF OPTICALLY-ACTIVE BETA-HYDROXY NITRILES USING A LIPASE [J].
ITOH, T ;
TAKAGI, Y ;
NISHIYAMA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1521-1524
[10]   Biocatalysis in ionic liquids: Markedly enhanced enantioselectivity of lipase [J].
Kim, KW ;
Song, B ;
Choi, MY ;
Kim, MJ .
ORGANIC LETTERS, 2001, 3 (10) :1507-1509