Immobilized hydroxynitrile lyases for enantioselective synthesis of cyanohydrins: Sol-gels and cross-linked enzyme aggregates

被引:37
作者
Cabirol, Fabien L.
Hanefeld, Ulf
Sheldon, Roger A.
机构
[1] Delft Univ Technol, Lab Biocatalysis & Organ Chem, NL-2628 BL Delft, Netherlands
[2] Inst Chem & Engn Sci, Singapore 627833, Singapore
关键词
asymmetric synthesis; CLEA; cyanohydrins; hydroxynitrile lyase; oxynitrilase; sol-gel;
D O I
10.1002/adsc.200606139
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The hydroxynitrile lyases (HNLs) from Prunus amygdalus (PaHNL), Manihot esculenta (MeHNL), and Hevea brasiliensis (HbHNL) were successfully immobilized in sol-gels. The cross-linked enzyme aggregate (CLEA) of HbHNL was also prepared. These immobilized enzymes and the commercial PaHNL- and MeHNL-CLEAs were employed for the enantioselective synthesis of cyanohydrins. The sol-gels were highly efficient at low catalyst loading and particularly stable towards the organic solvent (diisopropyl ether) and substrate/product deactivation. The stabilization effect was inconsistent for CLEAs of different HNLs and significant deactivation of PaHNL- and HbHNL-CLEAs in diisopropyl ether was observed. In contrast commercial MeHNL-CLEA proved to be a remarkably robust and efficient biocatalyst in diisopropyl ether.
引用
收藏
页码:1645 / 1654
页数:10
相关论文
共 36 条
[1]   Parameters influencing stability and activity of a S-hydroxynitrile lyase from Hevea brasiliensis in two-phase systems [J].
Bauer, M ;
Griengl, H ;
Steiner, W .
ENZYME AND MICROBIAL TECHNOLOGY, 1999, 24 (8-9) :514-522
[2]  
BLACKER J, 2005, CHEM IND, V20, P22
[3]   Chemically catalyzed asymmetric cyanohydrin syntheses [J].
Brunel, JM ;
Holmes, IP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (21) :2752-2778
[4]  
Budavari S., 1996, MERCK INDEX, V12th
[5]   Substrate specificity of mutants of the hydroxynitrile lyase from Manihot esculenta [J].
Bühler, H ;
Effenberger, F ;
Förster, S ;
Roos, J ;
Wajant, H .
CHEMBIOCHEM, 2003, 4 (2-3) :211-216
[6]   Immobilised enzymes: carrier-bound or carrier-free? [J].
Cao, LQ ;
van Langen, L ;
Sheldon, RA .
CURRENT OPINION IN BIOTECHNOLOGY, 2003, 14 (04) :387-394
[7]   Cross-linked aggregates of the hydroxynitrile lyase from Manihot esculenta:: Highly active and robust biocatalysts [J].
Chmura, Andrzej ;
van der Kraan, Geert M. ;
Kielar, Filip ;
van Langen, Luuk M. ;
van Rantwijk, Fred ;
Sheldon, Roger A. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1655-1661
[8]   Cross-linked crystals of hydroxynitrile lyase as catalyst for the synthesis of optically active cyanohydrins [J].
Costes, D ;
Wehtje, E ;
Adlercreutz, P .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) :607-612
[9]   Hydroxynitrile lyase-catalyzed synthesis of cyanohydrins in organic solvents - Parameters influencing activity and enantiospecificity [J].
Costes, D ;
Wehtje, E ;
Adlercreutz, P .
ENZYME AND MICROBIAL TECHNOLOGY, 1999, 25 (3-5) :384-391
[10]   ENZYME-CATALYZED ADDITION OF HYDROCYANIC ACID TO SUBSTITUTED PIVALALDEHYDES - A NOVEL SYNTHESIS OF (R)-PANTOLACTONE [J].
EFFENBERGER, F ;
EICHHORN, J ;
ROOS, J .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :271-282