A rational design of phosphonium salt type ionic liquids for ionic liquid coated-lipase catalyzed reaction

A rational design of phosphonium ionic liquid for ionic liquid coated-lipase (IL1-PS)-catalyzed reaction has been investigated, and very rapid transesterification of secondary alcohols accomplished when IL1-PS was used as catalyst in 2-methoxyethoxymethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)amide ([P444MEM][NTf2]) as solvent while perfect enantioselectivity was maintaining. Increased Kcat value was suggested to be the most important factor in IL1-PS working the best in [P444MEM][NTf2] solvent.

[1]  Muhammad Moniruzzaman,et al.  Recent advances of enzymatic reactions in ionic liquids , 2010 .

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

[3]  Hua Zhao,et al.  Enantioseparation of the esters of α‐N‐acetyl amino acids by lipase in ionic liquid , 2005 .

[4]  T. Tan,et al.  Functional dependency of structures of ionic liquids: do substituents govern the selectivity of enzymatic glycerolysis? , 2006, Organic & biomolecular chemistry.

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

[6]  Xiao‐Qi Yu,et al.  Enhancement of enantioselectivity in lipase-catalyzed resolution of N-(2-ethyl-6-methylphenyl)alanine by additives , 2006 .

[7]  C. Chiappe,et al.  Application of hydrophilic ionic liquids as co-solvents in chloroperoxidase catalyzed oxidations , 2006 .

[8]  T. Itoh,et al.  Novel supporting materials of lipase PS suitable for use in an ionic liquid solvent system , 2003 .

[9]  A. Russell,et al.  Enzymatic Catalysis of Formation of Z‐Aspartame in Ionic Liquid − An Alternative to Enzymatic Catalysis in Organic Solvents , 2000, Biotechnology progress.

[10]  P. Lozano,et al.  Enzymes in neoteric solvents: From one-phase to multiphase systems , 2010 .

[11]  M. Morimoto,et al.  Increased enantioselectivity and remarkable acceleration of lipase-catalyzed transesterification by using an imidazolium PEG-alkyl sulfate ionic liquid. , 2006, Chemistry.

[12]  C. Sih,et al.  Quantitative analyses of biochemical kinetic resolutions of enantiomers , 1982 .

[13]  Hua Zhao Effect of ions and other compatible solutes on enzyme activity, and its implication for biocatalysis using ionic liquids , 2005 .

[14]  T. Itoh,et al.  Efficient Lipase-catalyzed Enantioselective Acylation under Reduced Pressure Conditions in an Ionic Liquid Solvent System. , 2002 .

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

[16]  Hua Zhao,et al.  High transesterification activities of immobilized proteases in new ether-functionalized ionic liquids , 2010, Biotechnology Letters.

[17]  R. Kazlauskas,et al.  Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations. , 2001, The Journal of organic chemistry.

[18]  J. Iborra,et al.  Understanding structure-stability relationships of Candida antartica lipase B in ionic liquids. , 2005, Biomacromolecules.

[19]  Hua Zhao,et al.  Methods for stabilizing and activating enzymes in ionic liquids--a review , 2010 .

[20]  Zaijun Li,et al.  Improved activity and stability of pseudomonas capaci lipase in a novel biocompatible ionic liquid, 1‐isobutyl‐3‐methylimidazolium hexafluorophosphate , 2008 .

[21]  M. Moniruzzaman,et al.  Water-in-ionic liquid microemulsions as a new medium for enzymatic reactions , 2008 .

[22]  T. Itoh,et al.  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 , 2003 .

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

[24]  S. Shirakami,et al.  Lipase-Catalyzed Enantioselective Acylation in the Ionic Liquid Solvent System: Reaction of Enzyme Anchored to the Solvent , 2001 .

[25]  J. Iborra,et al.  Stabilization of α‐chymotrypsin by ionic liquids in transesterification reactions , 2001 .

[26]  K. R. Seddon,et al.  Applications of ionic liquids in the chemical industry. , 2008, Chemical Society reviews.

[27]  T. Itoh,et al.  Remarkable Activation of an Enzyme by (R)-Pyrrolidine-Substituted Imidazolium Alkyl PEG Sulfate , 2008 .

[28]  R. Sheldon,et al.  Lipase-catalyzed reactions in ionic liquids. , 2000, Organic letters.

[29]  Yun Hongwei,et al.  Kinetic resolution of ibuprofen catalyzed by Candida rugosa lipase in ionic liquids. , 2005, Chirality.

[30]  U. Kragl,et al.  Enzyme catalysis in ionic liquids: lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselectivity , 2001 .

[31]  T. Ema,et al.  Hydrolase-catalyzed Kinetic Resolution of 5-[4-(1-Hydroxyethyl)phenyl]-10,15,20-tris(pentafluorophenyl)porphyrin in Ionic Liquids , 2008 .

[32]  T. Itoh,et al.  Lipase-catalyzed Enantioselective Acylation in a Halogen Free Ionic Liquid Solvent System , 2003 .

[33]  T. Itoh,et al.  Enhanced enantioselectivity and remarkable acceleration on the lipase-catalyzed transesterification using novel ionic liquids , 2004 .

[34]  Roger A. Sheldon,et al.  Dissolution of Candida antarctica lipase B in ionic liquids: effects on structure and activity , 2004 .

[35]  Y. Tsukada,et al.  Preparation of novel hydrophobic fluorine-substituted-alkyl sulfate ionic liquids and application as an efficient reaction medium for lipase-catalyzed reaction , 2006 .

[36]  B Jastorff,et al.  Design of sustainable chemical products--the example of ionic liquids. , 2007, Chemical reviews.

[37]  Hua Zhao,et al.  Effect of kosmotropicity of ionic liquids on the enzyme stability in aqueous solutions. , 2006, Bioorganic chemistry.

[38]  T. Itoh,et al.  Synthesis of enantiomerically pure cycloalkenols via combination strategy of enzyme-catalyzed reaction and RCM reaction , 2007 .

[39]  Hua Zhao,et al.  Lipase dissolution and stabilization in ether-functionalized ionic liquids , 2009 .

[40]  R. Sheldon,et al.  Biocatalysis in ionic liquids. , 2007, Chemical reviews.

[41]  Hua Zhao,et al.  Kinetic Study on the Enzymatic Resolution of Homophenylalanine Ester Using Ionic Liquids , 2003, Biotechnology progress.

[42]  C. Afonso,et al.  One-pot enzymatic resolution and separation of sec-alcohols based on ionic acylating agents. , 2007, Angewandte Chemie.

[43]  J. Iborra,et al.  On the nature of ionic liquids and their effects on lipases that catalyze ester synthesis. , 2009, Journal of biotechnology.

[44]  G. Baker,et al.  Designing enzyme-compatible ionic liquids that can dissolve carbohydrates , 2008 .

[45]  G J Lye,et al.  Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations. , 2000, Biotechnology and bioengineering.

[46]  Hua Zhao,et al.  Enzymatic resolution of amino acid esters using ionic liquid N-ethyl pyridinium trifluoroacetate , 2002, Biotechnology Letters.

[47]  Chul-Woong Cho,et al.  Environmental fate and toxicity of ionic liquids: a review. , 2010, Water research.

[48]  Toshiyuki Itoh,et al.  Design of phosphonium ionic liquids for lipase-catalyzed transesterification , 2008 .

[49]  K W Kim,et al.  Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase. , 2001, Organic letters.

[50]  U. Kragl,et al.  Ionic liquids for aqueous two‐phase extraction and stabilization of enzymes , 2008, Biotechnology and bioengineering.

[51]  T. Itoh,et al.  Design of ionic liquids as a medium for the Grignard reaction , 2007 .