Investigation of ionic liquids as reaction media for enzymatic enantioselective acylation of amines

被引:72
作者
Irimescu, R [1 ]
Kato, K [1 ]
机构
[1] AIST, Biofunct Ceram Grp, Ceram Res Inst, Moriyama Ku, 2266-98 Anagahora, Nagoya, Aichi 4638560, Japan
基金
日本学术振兴会;
关键词
enantioselective amine acylation; ionic liquids; lipase; 4-pentenoic acid; solvent properties;
D O I
10.1016/j.molcatb.2004.05.003
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
The use of ionic liquids as reaction media for lipase-catalyzed enantioselective acylation of 1-phenylethylamine (1) and 2-phenyl-1-propylamine (2) with 4-pentenoic acid was investigated. The best performing ionic liquid for each of these amines as well as its solvent properties were very different. Preparative scale kinetic resolution of 1 was performed efficiently in 1-butyl-2,3-dimethylimidazolium trifluoromethanesulphonate. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:189 / 194
页数:6
相关论文
共 20 条
[1]  
BORNSCHEUER UT, 1999, HYDROLASES ORGANIC S, P103
[2]  
Carmichael AJ, 2000, J PHYS ORG CHEM, V13, P591, DOI 10.1002/1099-1395(200010)13:10<591::AID-POC305>3.0.CO
[3]  
2-2
[4]   Non-conventional hydrolase chemistry: Amide and carbamate bond formation catalyzed by lipases [J].
Gotor, V .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (10) :2189-2197
[5]   Lipase-catalyzed enantioselective reaction of amines with carboxylic acids under reduced pressure in non-solvent system and in ionic liquids [J].
Irimescu, R ;
Kato, K .
TETRAHEDRON LETTERS, 2004, 45 (03) :523-525
[6]   Enzymatic kinetic resolution of primary alcohols by direct esterification in solvent-free system [J].
Irimescu, R ;
Saito, T ;
Kato, K .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 27 (2-3) :69-73
[7]   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
[8]   Efficient lipase-catalyzed enantioselective acylation under reduced pressure conditions in an ionic liquid solvent system [J].
Itoh, T ;
Akasaki, E ;
Nishimura, Y .
CHEMISTRY LETTERS, 2002, (02) :154-155
[9]   Enzyme catalysis in ionic liquids [J].
Kragl, U ;
Eckstein, M ;
Kaftzik, N .
CURRENT OPINION IN BIOTECHNOLOGY, 2002, 13 (06) :565-571
[10]   DONOR NUMBERS OF ANIONS IN SOLUTION - THE USE OF SOLVATOCHROMIC LEWIS-ACID BASE INDICATORS [J].
LINERT, W ;
JAMESON, RF ;
TAHA, A .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (21) :3181-3186