Methods to increase enantioselectivity of lipases and esterases.

Lipases and esterases are frequently used in the synthesis of optically pure compounds; however, natural enzymes do not always show sufficiently high enantioselectivity. Variation of the structure of the substrates, modification of the reaction system or protein engineering (e.g. the expression of pure enzymes, rational design or directed evolution) are strategies that can be employed to improve the distinction between two enantiomers or enantiotopic groups.

[1]  Jürgen Pleiss,et al.  Activity of lipases and esterases towards tertiary alcohols: insights into structure-function relationships. , 2002, Angewandte Chemie.

[2]  Uwe T Bornscheuer,et al.  By Overexpression in the Yeast Pichia pastoris to Enhanced Enantioselectivity: New Aspects in the Application of Pig Liver Esterase. , 2001, Angewandte Chemie.

[3]  D. Tai,et al.  Enhancement of the enantioselectivity of lipase OF catalyzed hydrolysis , 2001 .

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

[5]  K. Hult,et al.  Creation of an enantioselective hydrolase by engineered substrate-assisted catalysis. , 2001, Journal of the American Chemical Society.

[6]  R. Kazlauskas,et al.  Molecular modeling and biocatalysis: explanations, predictions, limitations, and opportunities. , 2000, Current opinion in chemical biology.

[7]  Karlheinz Drauz,et al.  Enzyme Catalysis in Organic Synthesis , 1995 .

[8]  Per Berglund Controlling lipase enantioselectivity for organic synthesis. , 2001, Biomolecular engineering.

[9]  U. Kragl,et al.  Enhanced enantioselectivity of lipase from Pseudomonas sp. at high temperatures and fixed water activity in the ionic liquid, 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide , 2002, Biotechnology Letters.

[10]  Jürgen Pleiss,et al.  Lipase Engineering Database , 2000, German Conference on Bioinformatics.

[11]  R. Verger,et al.  Lipases: Interfacial Enzymes with Attractive Applications. , 1998, Angewandte Chemie.

[12]  R. Kazlauskas,et al.  Molecular basis for enantioselectivity of lipase from Chromobacterium viscosum toward the diesters of 2,3-dihydro-3-(4'-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol. , 2001, Journal of Organic Chemistry.

[13]  C. Craik,et al.  Engineering enzyme specificity. , 1998, Current opinion in chemical biology.

[14]  U. Bornscheuer,et al.  Enantioselective Hydrolysis ofd,l-Menthyl Benzoate toL-(-)-Menthol by RecombinantCandida rugosa Lipase LIP1 , 2002 .

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

[16]  R D Schmid,et al.  Stereoselectivity of Pseudomonas cepacia lipase toward secondary alcohols: A quantitative model , 2000, Protein science : a publication of the Protein Society.

[17]  Kurt Faber,et al.  Biotransformations in Organic Chemistry , 1992 .

[18]  A. Ménez,et al.  Tailoring new enzyme functions by rational redesign. , 2000, Current opinion in structural biology.

[19]  K. Kaihatsu,et al.  Effects of Chemical Modification of Lipase on Its Enantioselectivity in Organic Solvents. , 2001 .

[20]  UejiShin-ichi,et al.  A Dramatic Improvement of Enantioselectivity of Lipase in Organic Solvents by Addition of Aqueous SDS: A Close Correlation between Enantioselectivity and Conformational Flexibility of Lipase , 2001 .

[21]  T. Norin,et al.  Molecular Modelling of Lipase Catalysed Reactions. Prediction of Enantioselectivities , 1999 .

[22]  E. Toone,et al.  Enzymes in organic synthesis. 42. Investigation of the effects of the isozymal composition of pig liver esterase on its stereoselectivity in preparative-scale ester hydrolysis of asymmetric synthetic value , 1988 .

[23]  F. Arnold,et al.  Directed evolution of biocatalysts. , 1999, Current opinion in chemical biology.

[24]  P. Wasserscheid,et al.  Ionic Liquids-New "Solutions" for Transition Metal Catalysis. , 2000, Angewandte Chemie.

[25]  Manfred T. Reetz,et al.  Directed Evolution of an Enantioselective Enzyme through Combinatorial Multiple-Cassette Mutagenesis. , 2001, Angewandte Chemie.

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

[27]  F. Theil,et al.  Separation of Enantiomers by Extraction Based on Lipase-Catalyzed Enantiomer-Selective Fluorous-Phase Labeling. , 2001, Angewandte Chemie.

[28]  U. Bornscheuer Directed Evolution of Enzymes for Biocatalytic Applications , 2001 .

[29]  U. Bornscheuer,et al.  Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations , 1999 .

[30]  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.

[31]  S. Swaleh,et al.  Resolution of 1-(2-naphthyl)ethanol by a combination of an enzyme-catalyzed kinetic resolution with a fluorous triphasic separative reaction. , 2002, Organic letters.

[32]  U. Kragl,et al.  Enzyme catalysis in ionic liquids. , 2002, Current opinion in biotechnology.

[33]  H. Scheib,et al.  Computer-aided molecular modeling of the enantioselectivity of Pseudomonas cepacia lipase toward γ- and δ-lactones , 2000 .

[34]  M. Nardini,et al.  Directed evolution of an enantioselective lipase. , 2000, Chemistry & biology.

[35]  U. Bornscheuer,et al.  Improved biocatalysts by directed evolution and rational protein design. , 2001, Current opinion in chemical biology.

[36]  C. Schmidt-Dannert,et al.  Cloning, Functional Expression, and Characterization of Recombinant Pig Liver Esterase , 2001, Chembiochem : a European journal of chemical biology.

[37]  Karl Hult,et al.  Influence of acyl chain length on the enantioselectivity of Candida antarctica lipase B and its thermodynamic components in kinetic resolution of sec-alcohols , 2001 .

[38]  J. Reymond,et al.  Novel methods for biocatalyst screening. , 2001, Current opinion in chemical biology.

[39]  U. Bornscheuer,et al.  Lipase-Catalyzed Resolution of Ibuprofen , 2000 .

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

[41]  K. Hult,et al.  Improved Enantioselectivity of a Lipase by Rational Protein Engineering , 2001, Chembiochem : a European journal of chemical biology.

[42]  Keiichi Watanabe,et al.  Dimethyl sulfoxide as a co-solvent dramatically enhances the enantioselectivity in lipase-catalysed resolutions of 2-phenoxypropionic acyl derivatives , 2001 .

[43]  K. Hult,et al.  Enantiotopic Selectivity of-Pig Liver Esterase Isoenzymes , 1990 .

[44]  Kai Johnsson,et al.  Directed molecular evolution of proteins , 2002 .

[45]  K. Achiwa,et al.  Drastic solvent effect on lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines , 1992 .

[46]  A. Margolin,et al.  CROSS-LINKED CRYSTALS OF CANDIDA RUGOSA LIPASE : HIGHLY EFFICIENT CATALYSTS FOR THE RESOLUTION OF CHIRAL ESTERS , 1995 .