Immobilised Burkholderia cepacia lipase in dry organic solvents and ionic liquids: A comparison

被引：42
作者：
Hara, Piia [1 ,2 ]
Hanefeld, Ulf [3 ]
Kanerv, Liisa T. [1 ,2 ]
机构：
[1] Univ Turku, Dept Pharmacol Drug Dev & Therapeut, Lab Synth Drug Chem, FIN-20520 Turku, Finland
[2] Univ Turku, Dept Chem, FIN-20520 Turku, Finland
[3] Tech Univ Delft, Afdeling Biotechnol, NL-2628 BL Delft, Netherlands
来源：
GREEN CHEMISTRY | 2009年 / 11卷 / 02期
基金：
芬兰科学院;
关键词：
CATALYZED ENANTIOSELECTIVE ACYLATION; DYNAMIC KINETIC RESOLUTION; MANDELONITRILE ACETATE; VINYL-ACETATE; ENZYME; BIOCATALYSIS; SYSTEM; WATER; TRANSESTERIFICATION; TRANSFORMATIONS;
D O I：
10.1039/b814606c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Lipase PS from Burkholderia cepacia in its free, commercial form (BCL-PS), immobilised in a sol-gel (BCLxero) and as a CLEA (BCL-CLEA) was tested in dry organic solvents, ionic liquids and their mixtures. Utilising the acylations of secondary alcohols 1-3 the influence of the enzyme preparation on its activity and enantioselectivity was studied. BCL-CLEA displays higher activity (initial rates) than BCLxero for all substrates in the ILs but loses its activity rapidly. Thus, BCLxero is suitable for kinetic resolution in ILs and in their mixtures with organic solvents. It is not possible to label one IL better than the other without taking the nature of the substrate into account. In neat solvents, the nature of the solvent affects enantioselectivity (E) only when furyl-substituted alcohol 2 serves as a substrate while variation in E is more evident for reactions in solvent mixtures.
引用
收藏
页码：250 / 256
页数：7
相关论文
共 42 条
  • [1] Biocatalysis in non-conventional media-ionic liquids, supercritical fluids and the gas
    Cantone, Sara
    Hanefeld, Ulf
    Basso, Alessandra
    [J]. GREEN CHEMISTRY, 2007, 9 (09) : 954 - 971
  • [2] Ionic liquids: solvent properties and organic reactivity
    Chiappe, C
    Pieraccini, D
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (04) : 275 - 297
  • [3] An effective approach to the enantiomers of alicyclic β-aminonitriles by using lipase catalysis
    Fitz, M
    Lundell, K
    Lindroos, M
    Fülöp, F
    Kanerva, LT
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (22) : 3690 - 3697
  • [4] Chemoenzymatic preparation of enantiopure homoadamantyl β-amino acid and β-lactam derivatives
    Gyarmati, ZC
    Liljeblad, A
    Argay, G
    Kálmán, A
    Bernáth, G
    Kanerva, LT
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (05) : 566 - 572
  • [5] Reagents for (ir) reversible enzymatic acylations
    Hanefeld, U
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (14) : 2405 - 2415
  • [6] Sol-gels and cross-linked aggregates of lipase PS from Burkholderia cepacia and their application in dry organic solvents
    Hara, Piia
    Hanefeld, Ulf
    Kanerva, Liisa T.
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2008, 50 (2-4) : 80 - 86
  • [7] Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation
    Huddleston, JG
    Visser, AE
    Reichert, WM
    Willauer, HD
    Broker, GA
    Rogers, RD
    [J]. GREEN CHEMISTRY, 2001, 3 (04) : 156 - 164
  • [8] Novel supporting materials of lipase PS suitable for use in an ionic liquid solvent system
    Itoh, T
    Ouchi, N
    Nishimura, Y
    Hui, HS
    Katada, N
    Niwa, M
    Onaka, M
    [J]. GREEN CHEMISTRY, 2003, 5 (05) : 494 - 496
  • [9] Itoh T, 2003, ACS SYM SER, V856, P251
  • [10] 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
    Itoh, T
    Nishimura, Y
    Ouchi, N
    Hayase, S
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 26 (1-2) : 41 - 45
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