Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: aspects on the preparation and enantiopreference

被引:26
作者
Brem, Juergen [1 ,2 ,3 ]
Liljeblad, Arto [1 ,2 ]
Paizs, Csaba [3 ]
Tosa, Monica Ioana [3 ]
Irimie, Florin-Dan [3 ]
Kanerva, Liisa T. [1 ,2 ]
机构
[1] Univ Turku, Inst Biomed, Dept Pharmacol Drug Dev & Therapeut, Lab Synthet Drug Chem, FIN-20014 Turku, Finland
[2] Univ Turku, Dept Chem, FIN-20014 Turku, Finland
[3] Univ Babes Bolyai, Dept Biochem & Biochem Engn, RO-400028 Cluj Napoca, Romania
关键词
CATALYZED KINETIC RESOLUTION; ACID-DERIVATIVES; ESTERS; ALCOHOLS;
D O I
10.1016/j.tetasy.2011.01.027
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The preparative scale kinetic resolution of racemic ethyl 2- and 3-furyl- and 2- and 3-thienyl-3-hydroxypropanoates has been performed by Candida antarctica lipases A and B with vinyl esters. A study based on the present work together with the literature has been carried out in terms of lipase enantiopreference and substrate structure. We also discuss the excellent behavior of the lipase A in O-acylations of secondary alcohols with respect to enantiopreference. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:315 / 322
页数:8
相关论文
共 54 条
[21]   Enantioselective synthesis of β-hydroxy acid derivatives via a one-pot aldol reaction-dynamic kinetic resolution [J].
Huerta, FF ;
Bäckvall, JE .
ORGANIC LETTERS, 2001, 3 (08) :1209-1212
[22]   ENZYMATIC ACYLATION IN THE RESOLUTION OF METHYL THREO-2-HYDROXY-3-(4-METHOXYPHENYL)-3-(2-X-PHENYLTHIO)PROPIONATES IN ORGANIC-SOLVENTS [J].
KANERVA, LT ;
SUNDHOLM, O .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (20) :2407-2410
[23]  
Kanerva LT, 2010, ENCY CATALYSIS, DOI [DOI 10.1002/0471227617.EOC197, 10.1002/0471227617.eoc197]
[24]   A RULE TO PREDICT WHICH ENANTIOMER OF A SECONDARY ALCOHOL REACTS FASTER IN REACTIONS CATALYZED BY CHOLESTEROL ESTERASE, LIPASE FROM PSEUDOMONAS-CEPACIA, AND LIPASE FROM CANDIDA-RUGOSA [J].
KAZLAUSKAS, RJ ;
WEISSFLOCH, ANE ;
RAPPAPORT, AT ;
CUCCIA, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2656-2665
[25]   Lipases from Candida antarctica:: Unique biocatalysts from a unique origin [J].
Kirk, O ;
Christensen, MW .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (04) :446-451
[26]   In vitro activity of tebipenem, a new oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae [J].
Kobayashi, R ;
Konomi, M ;
Hasegawa, K ;
Morozumi, M ;
Sunakawa, K ;
Ubukata, K .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2005, 49 (03) :889-894
[27]   Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines [J].
Lee, Jin Hee ;
Han, Kiwon ;
Kim, Mahn-Joo ;
Park, Jaiwook .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (06) :999-1015
[28]   Lipases in β-dipeptide synthesis in organic solvents [J].
Li, Xiang-Guo ;
Kanerva, Liisa T. .
ORGANIC LETTERS, 2006, 8 (24) :5593-5596
[29]   Enzymatic methods for the preparation of enantiopure malic and aspartic acid derivatives in organic solvents [J].
Liljeblad, A ;
Kanerva, LT .
TETRAHEDRON-ASYMMETRY, 1999, 10 (22) :4405-4415
[30]   Biocatalysis as a profound tool in the preparation of highly enantiopure β-amino acids [J].
Liljeblad, Arto ;
Kanerva, Liisa T. .
TETRAHEDRON, 2006, 62 (25) :5831-5854