Design of phosphonium ionic liquids for lipase-catalyzed transesterification

Abstract Ionic liquids are now recognized as solvents for use in lipase-catalyzed reactions; however, there still remains a serious drawback in that the rate of reaction in an ionic liquid is slower than that in a conventional organic solvent. To overcome this problem, attempts have been made to evolve phosphonium ionic liquids appropriate for lipase-catalyzed reaction; several types of phosphonium salts have been prepared and their capability evaluated for use as solvent for the lipase-catalyzed reaction. Very rapid lipase PS-catalyzed transesterification of secondary alcohols was obtained when 2-methoxyethyl(tri- n -butyl)phosphonium bis(trifluoromethanesulfonyl)imide ([MEBu 3 P][NTf 2 ]) was used as solvent, affording the first example of a reaction rate superior to that in diisopropyl ether.

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

[2]  C. Seto,et al.  Using a lipase as a high-throughput screening method for measuring the enantiomeric excess of allylic acetates. , 2003, The Journal of organic chemistry.

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

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

[5]  Sushma Chauhan,et al.  Chemical and biochemical transformations in ionic liquids , 2005 .

[6]  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 .

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

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

[9]  A. Ghanem,et al.  Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol , 2003 .

[10]  Robin D. Rogers,et al.  Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate , 2003 .

[11]  G. S. Reddy,et al.  Excess volumes, densities, speeds of sound and viscosities for the binary systems of diisopropyl ether with hydrocarbons at 303.15 K , 2006 .

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

[13]  Ram S. Mohan,et al.  Reactivity of ionic liquids , 2007 .

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

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

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

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

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

[19]  Peter Wasserscheid,et al.  Ionic Liquids in Synthesis , 2002 .

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

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

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

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

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

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

[26]  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 .

[27]  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.

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