The study on efficient hydrolases immobilization for the kinetic resolution of the α-acetoxyamides

被引:14
作者
Koszelewski, Dominik [1 ]
Redzej, Adam [1 ]
Ostaszewski, Ryszard [1 ]
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
关键词
enzymatic kinetic resolution; Passerini reaction; lipases; enantioselectivity; immobilization;
D O I
10.1016/j.molcatb.2007.03.007
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
Using different immobilization protocols, the lipases from Pseudomonas cepacia (PCL) and porcine pancreas (PPL) were immobilised. The catalytic behaviour of the biocatalysts used in the hydrolytic resolution of the target compounds, viz., acetic acid phenyl(3,4,5-trimethoxybenzylcarbamoyl)methyl ester (3a) and acetic acid (3,4,5-trimethoxy benzylcarbamoyl)(3,4,5-trimethoxyphenyl)methyl ester (3b), in an aqueous environment, was investigated. The native lipases from P. cepacia (PCL) and porcine pancreas (PPL) showed low enantioselectivity (E= 5.1 and 3.5, respectively). Upon immobilization into a sol-gel matrix, the enantioselectivity of PCL improved significantly (from E= 5.1 up to 30.5). The covalent immobilization on Eupergit substantially increased the enzymatic activity as well as the enantioselectivity of PCL (E=34.0). (c) 2007 Elsevier B.V All rights reserved.
引用
收藏
页码:51 / 57
页数:7
相关论文
共 43 条
[1]  
Bastida A, 1998, BIOTECHNOL BIOENG, V58, P486, DOI 10.1002/(SICI)1097-0290(19980605)58:5<486::AID-BIT4>3.0.CO
[2]  
2-9
[3]   Identification of various lipolytic enzymes in crude porcine pancreatic lipase preparations using covalent fluorescent inhibitors [J].
Birner-Grünberger, R ;
Scholze, H ;
Faber, K ;
Hermetter, A .
BIOTECHNOLOGY AND BIOENGINEERING, 2004, 85 (02) :147-154
[4]  
Bornscheuer UT, 2006, HYDROLASES IN ORGANIC SYNTHESIS: REGIO- AND STEREOSELECTIVE BIOTRANSFORMATIONS, 2ND EDITION, P1
[5]  
BORNSCHEUER UT, 2000, BIOTECHNOLOGY SERI B, V8, P277
[6]   A MODEL FOR INTERFACIAL ACTIVATION IN LIPASES FROM THE STRUCTURE OF A FUNGAL LIPASE-INHIBITOR COMPLEX [J].
BRZOZOWSKI, AM ;
DEREWENDA, U ;
DEREWENDA, ZS ;
DODSON, GG ;
LAWSON, DM ;
TURKENBURG, JP ;
BJORKLING, F ;
HUGEJENSEN, B ;
PATKAR, SA ;
THIM, L .
NATURE, 1991, 351 (6326) :491-494
[7]  
Carrea G, 2000, ANGEW CHEM INT EDIT, V39, P2226
[8]   Enantioselectivity modulation through immobilization of Arthrobacter sp lipase:: Kinetic resolution of fluoxetine intermediate [J].
Chaubey, Asha ;
Parshad, Rajinder ;
Koul, Surrinder ;
Taneja, Subhash C. ;
Qazi, Ghulam N. .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2006, 42 (1-2) :39-44
[9]   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
[10]   CATALYSIS AT THE INTERFACE - THE ANATOMY OF A CONFORMATIONAL CHANGE IN A TRIGLYCERIDE LIPASE [J].
DEREWENDA, U ;
BRZOZOWSKI, AM ;
LAWSON, DM ;
DEREWENDA, ZS .
BIOCHEMISTRY, 1992, 31 (05) :1532-1541