Magnetic nanoparticles supported ionic liquids for lipase immobilization: Enzyme activity in catalyzing esterification

Candida rugosa lipase was immobilized on magnetic nanoparticles supported ionic liquids having different cation chain length (C(1), C(4) and C(8)) and anions (Cl(-), BF(4)(-) and PF(6)(-)). Magnetic nanoparticles Supported ionic liquids were obtained by covalent bonding of ionic liquids-silane on magnetic silica nanoparticles. The particles are superparamagnetic with diameter of about 55 nm. Large amount of lipase (63.89 mg/(100 mg carrier)) was loaded on the support through ionic adsorption. Activity of the immobilized lipase was examined by the catalysis of esterification between oleic acid and butanol. The activity of bound lipase was 118.3% compared to that of the native lipase. Immobilized lipase maintained 60% of its initial activity even when the temperature was LIP to 80 degrees C. In addition, immobilized lipase retained 60% of its initial activity after 8 repeated batches reaction, while no activity was detected after 6 cycles for the free enzyme. (C) 2008 Elsevier B.V. All rights reserved.

[1]  W. Hölderich,et al.  Immobilisation of chloroaluminate ionic liquids on silica materials , 2000 .

[2]  Tinghua Wu,et al.  Alkylation of Ammonium Salts Catalyzed by Imidazolium‐Based Ionic Liquid Catalysts , 2007 .

[3]  R. Gross,et al.  Effects of porous polystyrene resin parameters on Candida antarctica lipase B adsorption, distribution, and polyester synthesis activity. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[4]  P. He,et al.  Highly active horseradish peroxidase immobilized in 1-butyl-3-methylimidazolium tetrafluoroborate room-temperature ionic liquid based sol-gel host materials. , 2005, Chemical communications.

[5]  Jianmin Xing,et al.  Preparation and characterization of amino-silane modified superparamagnetic silica nanospheres , 2004 .

[6]  O. Abián,et al.  New Cationic Exchanger Support for Reversible Immobilization of Proteins , 2008, Biotechnology progress.

[7]  R. Sheldon,et al.  Structure and activity of Candida antarctica lipase B in ionic liquids , 2006 .

[8]  L. Deng,et al.  The preparation and catalytically active characterization of papain immobilized on magnetic composite microspheres , 2004 .

[9]  Abraham Ulman,et al.  Activity of Candida rugosa lipase immobilized on gamma-Fe2O3 magnetic nanoparticles. , 2003, Journal of the American Chemical Society.

[10]  Sang Hyun Lee,et al.  Using ionic liquids to stabilize lipase within sol–gel derived silica , 2007 .

[11]  Mahn-Joo Kim,et al.  Ionic liquid-coated enzyme for biocatalysis in organic solvent. , 2002, The Journal of organic chemistry.

[12]  S. Çelebi,et al.  Performance of immobilized glucoamylase in a magnetically stabilized fluidized bed reactor (MSFBR) , 2000 .

[13]  C. Ortiz,et al.  Lipase–lipase interactions as a new tool to immobilize and modulate the lipase properties , 2005 .

[14]  R. Fernández-Lafuente,et al.  Regioselective Hydrolysis of Different Peracetylated β‐Monosaccharides by Immobilized Lipases from Different Sources. Key Role of The Immobilization , 2007 .

[15]  Zhi‐Kang Xu,et al.  Catalase Immobilization on Electrospun Nanofibers: Effects of Porphyrin Pendants and Carbon Nanotubes , 2007 .

[16]  M. M. Bradford.  A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. , 1976, Analytical biochemistry.

[17]  Hiroyuki Ohno,et al.  Solubility and stability of cytochrome c in hydrated ionic liquids: effect of oxo acid residues and kosmotropicity. , 2007, Biomacromolecules.

[18]  Kai Luo,et al.  Preparation and characterization of dendritic composite magnetic particles as a novel enzyme immobilization carrier , 2006 .

[19]  Zheng Guo,et al.  Preparation and characterization of immobilized lipase on magnetic hydrophobic microspheres , 2003 .

[20]  Raymond A. Cook,et al.  Supported ionic liquid catalysis--a new concept for homogeneous hydroformylation catalysis. , 2002, Journal of the American Chemical Society.

[21]  Robin D. Rogers,et al.  Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation , 2001 .

[22]  Alan J Russell,et al.  Impact of ionic liquid physical properties on lipase activity and stability. , 2003, Journal of the American Chemical Society.

[23]  C. Serna,et al.  Synthesis of monodisperse superparamagnetic Fe/silica nanospherical composites. , 2003, Journal of the American Chemical Society.

[24]  E. García‐Verdugo,et al.  Bioreactors based on monolith-supported ionic liquid phase for enzyme catalysis in supercritical carbon dioxide , 2007 .

[25]  J. Finch,et al.  A Novel Two-Step Silica-Coating Process for Engineering Magnetic Nanocomposites , 1998 .

[26]  K. Marsh,et al.  Room temperature ionic liquids and their mixtures—a review , 2004 .

[27]  Lionel Teulé-Gay,et al.  Double plasma treatment-induced graft polymerization of carbohydrated monomers on poly(ethylene terephthalate) fibers. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[28]  Roger A. Sheldon,et al.  Enzyme Immobilization: The Quest for Optimum Performance , 2007 .

[29]  Direct binding procedure of proteins and enzymes to fine magnetic particles , 2002 .

[30]  J. C. Santos,et al.  Lipase‐catalyzed synthesis of butyl esters by direct esterification in solvent‐free system , 2007 .

[31]  Zhi‐Kang Xu,et al.  Nanofibrous poly(acrylonitrile-co-maleic acid) membranes functionalized with gelatin and chitosan for lipase immobilization. , 2006, Biomaterials.

[32]  Ping Wang.  Nanoscale biocatalyst systems. , 2006, Current opinion in biotechnology.

[33]  Elizabeth M. Miller,et al.  Effects of macroporous resin size on Candida antarctica lipase B adsorption, fraction of active molecules, and catalytic activity for polyester synthesis. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[34]  Chen Guo,et al.  Enzymatic Hydrolysis of Penicillin in Mixed Ionic Liquids/Water Two‐Phase System , 2007, Biotechnology progress.

[35]  S. Barreiros,et al.  Enzymatic resolution of Indinavir precursor in ionic liquids with reuse of biocatalyst and media by product sublimation , 2007 .

[36]  W. Norde,et al.  Adsorption of lipase from Candida rugosa on cellulose and its influence on lipolytic activity , 1992 .

[37]  Huizhou Liu,et al.  Immobilization of lipase onto micron-size magnetic beads. , 2005, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[38]  Frances H. Arnold,et al.  Metal-coordination interactions in the template-mediated synthesis of substrate-selective polymers recognition of bis(imidazole) substrates by copper(II) iminodiacetate containing polymers , 1992 .

[39]  S. F. D’souza,et al.  IMMOBILIZED ENZYMES IN BIOPROCESS , 1999 .

[40]  Tapas Sen,et al.  Surface modification of magnetic nanoparticles with alkoxysilanes and their application in magnetic bioseparations. , 2005, Langmuir : the ACS journal of surfaces and colloids.

[41]  Keehoon Won,et al.  Optimization of lipase entrapment in Ca-alginate gel beads , 2005 .

[42]  R. Fernández-Lafuente,et al.  Modulation of Immobilized Lipase Enantioselectivity via Chemical Amination , 2007 .