Customizing lipases for biocatalysis: a survey of chemical, physical and molecular biological approaches

Journal of Molecular Catalysis B: Enzymatic - Tập 9 Số 4-6 - Trang 113-148 - 2000
Pierre Villeneuve1, J.M. Muderhwa2, Jean Graille1, Michael J. Haas3
1Laboratoire de Lipotechnie, CIRAD-AMIS, SMANA, BP5035, 34032 Montpellier Cedex 1, France
2Department of Membrane Biochemistry, Walter Reed Army Institute of Research, Washington, DC 20307–5100, USA
3Hides, Lipids and Wool Research Unit, US Department of Agriculture, Agricultural Research Service, Eastern Regional Research Center, 600 East Mermaid Lane, Wyndmoor, PA 19038, USA

Tóm tắt

Từ khóa


Tài liệu tham khảo

Schmidt, 1998, Lipases: interfacial enzymes with attractive applications, Angew. Chem. Int. Ed. Engl., 37, 1608, 10.1002/(SICI)1521-3773(19980703)37:12<1608::AID-ANIE1608>3.0.CO;2-V

Kazlauskas, 1998, Biotransformations with lipases, Vol. 8a, 37

Alberghina, 1998, Lipases and lipids: structure, specificity and applications in biocatalysis, Chem. Phys. Lipids, 93

Farooqui, 1987, Phospholipases, lysophospholipases and lipases and their involvement in various diseases, Neurochem. Pathol., 7, 99, 10.1007/BF02834212

Shinomura, 1991, Synergistic action of diacylglycerol and unsaturated fatty acid for protein kinase C activation: its possible implications, Proc. Natl. Acad. Sci. U.S.A., 88, 5149, 10.1073/pnas.88.12.5149

Klibanov, 1989, Enzymatic catalysis in anhydrous organic solvents, TIBS, 14, 141

Gupta, 1992, Enzyme function in organic solvents, Eur. J. Biochem., 203, 25, 10.1111/j.1432-1033.1992.tb19823.x

Brink, 1988, Biocatalysis in organic media, Enzyme Microb. Technol., 10, 736, 10.1016/0141-0229(88)90118-4

Martinek, 1986, Micellar enzymology, Eur. J Biochem., 155, 453, 10.1111/j.1432-1033.1986.tb09512.x

Nagao, 1990, Lipase-catalyzed synthesis of fatty acid esters useful in the food industry: e.g. triglyceride preparation using lipase in reversed micelles: a review, Biocatalysis, 3, 295, 10.3109/10242429008992073

Gandhi, 1997, Applications of lipase, J. Am. Oil Chem. Soc., 74, 621, 10.1007/s11746-997-0194-x

Malcata, 1990, Immobilized lipase reactors fort modification of fats and oils — a review, J. Am. Oil Chem. Soc., 67, 890, 10.1007/BF02541845

Okumura, 1979, Synthesis of various kinds of esters by four microbial lipases, Biochim. Biophys. Acta, 575, 156, 10.1016/0005-2760(79)90141-3

Marlot, 1985, Ester synthesis in organic solvent catalyzed by lipases immobilized on hydrophilic supports, Biotechnol. Lett., 7, 647, 10.1007/BF01040202

Macrae, 1985, 195

Macrae, 1983, Lipase-catalyzed interesterification of oils and fats, J. Am. Oil Chem. Soc., 60, 291, 10.1007/BF02543502

Muderhwa, 1989, Interesterification enzymatique régiosélective 1–3 en milieu fondu et en réacteur continu: valorisation de l'huile de palme, Oleagineux, 44, 35

S. Bloomer. Lipase-catalyzed lipid modifications in non-aqueous media. PhD Thesis, Lund University, Sweden, 1992.

Montet, 1989, Synthesis of N-lauryloleylamide by the Mucor miehei lipase in an organic medium, Fat Sci. Technol., 91, 14

Kilara, 1977, The use of immobilized enzymes in the food industry, Crit. Rev. Food Sci. Nutr., 12, 161, 10.1080/10408397909527276

Omar, 1988, Hydrolysis of triglycerides by immobilized thermostable lipase from Humicola lanuginosa, Agric. Biol. Chem., 52, 99, 10.1271/bbb1961.52.99

Wisdom, 1985, Enzymic interestierification of fats: factors influencing the choice of support for immobilized lipase, Enzyme Microb. Technol., 7, 567, 10.1016/0141-0229(85)90102-4

Brady, 1988, Enzymatic interesterification of fats: factors influencing the choice of support for immobilized lipase, J. Am. Oil Chem. Soc., 65, 917, 10.1007/BF02544510

C. Brady, L. Metcalfe, D. Slaboszewski, D. Frank, Hydrolysis of liq. fats using lipase adsorbed on porous substrate of untreated microporous polyolefin, from aq. medium, using fixed bed or stirred reactors. US Patent No. 4,629,742, 1986.

C. Brady, L. Metcalfe, D. Slaboszewski, D. Frank, Diaphragm for hydrolysis of fats.Comprisinf layer of hydrophobic filter cloth layer of lipase immobilised on microporous polymer fibres and retaining screen.US Patent No. 4,678,580, 1987.

Kimura, 1983, Application of immobilized lipase to hydrolysis of triacylglyceride, Eur. J. Appl. Microbiol. Biotechnol., 17, 107, 10.1007/BF00499860

Kang, 1988, Effect of water on hydrolysis of olive oil by immobilized lipase in reverse phase system, Biotechnol. Lett., 10, 341, 10.1007/BF01026162

Svensson, 1990, Interesterification of phosphatidylcholine with lipases in organic media, Appl. Microbiol. Biotechnol., 33, 255, 10.1007/BF00164517

Gitlesen, 1997, Adsorption of lipase on polypropylene powder, Biochem. Biophys. Acta, 1345, 188, 10.1016/S0005-2760(96)00176-2

Gray, 1990, Immobilization of lipase from Candida cylindracea and its use in the synthesis of menthol esters by transesterification, Enzyme Microb. Technol., 12, 800, 10.1016/0141-0229(90)90155-J

Garcia, 1992, Use of Candida a rugosa lipase immobilized in a spiral wound membrane reactor for the hydrolysis of milkfat, Enzyme Microb. Technol., 14, 535, 10.1016/0141-0229(92)90124-7

Monsan, 1982, 91

Wahlgren, 1991, Protein adsorption to solid surfaces, TIBTECH, 9, 201, 10.1016/0167-7799(91)90064-O

Balcao, 1996, Bioreactors with immobilized lipases: state of the art, Enzyme Microb. Technol., 18, 392, 10.1016/0141-0229(95)00125-5

Montero, 1993, Immobilization of Candida rugosa lipase and some properties of the immobilized enzyme, Enzyme Microb. Technol., 15, 239, 10.1016/0141-0229(93)90144-Q

Weber, 1995, Sensitivity of microbial lipases to acetaldehyde formed by acyl-transfer reaction from vinyl esters, Biotechnol. Lett., 17, 803, 10.1007/BF00129008

Kaga, 1994, Stabilization of Candida lipase against acetaldehyde by adsorption onto Celite, Biotechnol. Tech., 8, 369, 10.1007/BF00154305

Bosley, 1997, Turning lipases into industrial biocatalysts, Biochem. Soc. Trans., 2, 174, 10.1042/bst0250174

Pronk, 1988, The hydrolysis of triglycerides by immobilized lipase in a hydrophilic membrane reactor, Biotechnol. Bioeng., 32, 512, 10.1002/bit.260320414

Gonçalves, 1997, Effect of the immobilization support on the hydrolytic activity of a cutinase from Fusarium solani Pisi, Enzyme Microb. Technol., 20, 93, 10.1016/S0141-0229(96)00089-0

Al-Duri, 1995, Hydrolysis of edible oils by lipases immobilized on hydrophobic supports : effect of internal support structure, J. Am. Oil Chem. Soc., 72, 1351, 10.1007/BF02546211

Shaw, 1990, Lipolytic activities of a lipase immobilized on six selected supporting materials, Biotechnol. Bioeng., 35, 132, 10.1002/bit.260350204

Ruckenstein, 1993, A novel support for the immobilization of lipase and the effects of the details of its preparation on the hydrolysis of triacylglycerides, Biotechnol. Tech., 7, 117, 10.1007/BF00157381

Bastida, 1998, A single step purification, immobilization and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports, Biotechnol. Bioeng., 58, 486, 10.1002/(SICI)1097-0290(19980605)58:5<486::AID-BIT4>3.0.CO;2-9

Fernandez-Lafuente, 1998, Immobilization of lipases by selective adsorption on hydrophobic supports, Chem. Phys. Lipids, 10.1016/S0009-3084(98)00042-5

Tantrakulsiri, 1997, Utilization of rice hull ash as a support material for immobilization of Candida cylindracea lipase, J. Am. Oil Chem. Soc., 74, 173, 10.1007/s11746-997-0165-2

Kogusi, 1995, Large scale immobilization of lipase from Pseudomonas fluorescens Biotype I and application for sardine oil hydrolysis, J. Am. Oil Chem., 72, 1281, 10.1007/BF02546200

Wehjte, 1992, Improved activity retention of enzymes deposited on solid supports, Biotechnol. Bioeng., 41, 171

Ruckenstein, 1993, Lipase immobilized on hydrophobic porous polymer supports prepared by concentrated emulsion polymerization and their activity in the hydrolysis of triacylglycerides, Biotechnol. Bioeng., 42, 821, 10.1002/bit.260420706

Ruckenstein, 1988, Polymerization in gel-like emulsions, J. Appl. Polym. Sci., 36, 907, 10.1002/app.1988.070360414

Bosley, 1997, Immobilization of lipases on porous polypropylene : reduction in esterification efficiency at low loadings, J. Am. Oil Chem. Soc., 74, 107, 10.1007/s11746-997-0153-6

Villeneuve, 1997, Lipase specificities : potential applications in lipid bioconversions, INFORM, 8, 640

Fureby, 1996, Acyl group migration in 2-monoolein, Biocatal. Biotrans., 14, 89, 10.3109/10242429609106879

Giordani, 1991, Tributyroylglycerol hydrolase activity in Carica papaya and other latices, Phytochemistry, 30, 1069, 10.1016/S0031-9422(00)95174-4

Villeneuve, 1995, Carica papaya latex lipase : sn-3 stereospecificity or short chain selectivity? Model chiral triglycerides are removing teh ambiguity, J. Am. Oil Chem. Soc., 72, 753, 10.1007/BF02635668

Mukherjee, 1996, Specificity of Carica papaya latex as biocatalyst in the esterification of fatty acids with 1-butanol, J. Agric. Food Chem., 44, 1948, 10.1021/jf960216d

Foglia, 1997, Carica papaya latex-catalyzed synthesis of structured triacylglycerols, J. Am. Oil Chem. Soc., 74, 1447, 10.1007/s11746-997-0252-4

Hertzberg, 1992, Alginate as immobilization matrix and stabilizing agent in two phases liquid system: application in lipase-catalyzed reaction, Enzyme Microb. Technol., 14, 42, 10.1016/0141-0229(92)90024-I

Janta, 1997, Biocatalysis using gelatin microemulsion-based organogels containing immobilized Chromobacterium viscosum lipase, Biotechnol. Bioeng., 53, 121, 10.1002/(SICI)1097-0290(19970120)53:2<121::AID-BIT1>3.0.CO;2-Q

Reetz, 1995, Efficient immobilization of lipases by entrapement in hydrophobic sol–gel materials, Biotechnol. Bioeng., 49, 527, 10.1002/(SICI)1097-0290(19960305)49:5<527::AID-BIT5>3.0.CO;2-L

M.W. Christensen, K.M. Larsson, H. Deussen, O. Kirk, Proceedings of the 89th AOCS Annual Meeting, Chicago, USA, May 10–13, 1998.

Guidoni, 1981, Characterization of the serine reacting with diethyl p-nitrophenyl phosphate in porcine pancreatic lipase, Biochim. Biophys. Acta, 660, 148, 10.1016/0005-2744(81)90120-0

Luthi-Peng, 1992, Identification if the active-site serine in human pancreatic lipase by chemical modification with tetrahydrolipstatin, FEBS, 299, 111, 10.1016/0014-5793(92)80112-T

Winkler, 1990, Structure of human pancreatic lipase, Nature, 343, 771, 10.1038/343771a0

Kaimal, 1989, The active site composition of porcine pancreatic lipase: possible involvement of lysine, Biochim. Biophys. Acta, 999, 331, 10.1016/0167-4838(89)90016-2

Means, 1968, Reductive alkylation of amino groups in proteins, Biochemistry, 7, 2192, 10.1021/bi00846a023

Kaimal, 1989, Enhancement of catalytic activity of porcine pancreatic lipase by reductive alkylation, Biotechnol. Lett., 11, 31, 10.1007/BF01026782

Kawase, 1989, Effect of chemical modification of amino acid residues on the activities of lipase from Candida cylindracea, Enzyme Microb. Technol., 11, 44, 10.1016/0141-0229(89)90112-9

Inada, 1984, Ester synthesis catalyzed by polyethylene-glycol modified lipase in benzene, Biochem. Biophys. Res. Commun., 122, 845, 10.1016/S0006-291X(84)80111-4

Kodera, 1986, Ester synthesis from alpha substituted carboxylic acid catalyzed by polyethylene glycol modified lipase from Candida cylindracea in benzene, Biotechnol. Lett., 8, 881, 10.1007/BF01078652

Baillargeon, 1988, Polyethylene glycol modification of Candida rugosa lipase, J. Am. Oil Chem. Soc., 65, 1812, 10.1007/BF02542388

Tamaura, 1986, Chemical modification of lipase with ferromagnetic modifier — a ferromagnetic modified lipase, Biotechnol. Lett., 8, 877, 10.1007/BF01078651

Murakami, 1993, Transesterification of oil by fatty acid-modified lipase, J. Am. Oil Chem. Soc., 70, 571, 10.1007/BF02545321

Basri, 1992, Immobilization of hydrophobic lipase derivatives onto organic polymers beads, J. Am. Oil Chem. Soc., 69, 579, 10.1007/BF02636112

Tsuzuki, 1991, Reactive properties of the organic solvent-soluble lipase, Biochim. Biophys. Acta, 1083, 201, 10.1016/0005-2760(91)90043-H

Abuchowski, 1977, Alteration of immunological of bovine serum albumin by covalent attachment of polyethylene glycol, J. Biol. Chem., 252, 3578, 10.1016/S0021-9258(17)40291-2

Abuchowski, 1977, Effect of covalent attachment of polyethylene glycol on immunogenecity and circulating life of bovine liver catalase, J. Biol. Chem., 252, 3582, 10.1016/S0021-9258(17)40292-4

Neklyudov, 1981, Properties of immobilized lipase from Rhizopus orizae, Prikl. Biokhim. Microbiol., 17, 510

Rakhimov, 1977, Substrates specificities of immobilized lipases, Doklady Biochem., 229, 389

Kilara, 1977, Preparation and properties of immobilized papain and lipase, Biotechnol. Bioeng., 19, 1703, 10.1002/bit.260191109

Kroll, 1980, Preparation and properties of the immobilized lipase from Geotrichum candidum, Die Nahrung, 24, 215, 10.1002/food.19800240303

Manjon, 1991, Short-chain flavour ester synthesis by immobilized lipase in organic media, Biotechnol. Lett., 13, 339, 10.1007/BF01027679

Stark, 1989, Covalent immobilization of lipase in organic solvents, Biotechnol. Bioeng., 34, 942, 10.1002/bit.260340709

Lieberman, 1975, Hydrolysis of particulate tributyrin in fluidized lipase reactor, Biotechnol. Bioeng., 17, 1401, 10.1002/bit.260171002

Lalonde, 1995, Cross-linked crystals of Candida rugosa lipase: highly efficient catalysts for the resolution of chiral esters, J. Am. Chem. Soc., 117, 6845, 10.1021/ja00131a006

Brady, 1990, A serine protease triad forms the catalytic centre of a triacylglycerol lipase, Nature (London), 343, 767, 10.1038/343767a0

Cygler, 1997, Structure as a basis for understanding interfacial properties of lipases, Vol. 284, 3

Drabløs, 1997, Identification of conserved residues in family of esterase and lipase sequences, Vol. 284, 28

Brzozowski, 1991, A model for interfacial activation in lipases from the structure of a fungal lipase-inhibitor complex, Nature (London), 351, 491, 10.1038/351491a0

Derewenda, 1992, Catalysis at the interface: the anatomy of a conformational change in a triglyceride lipase, Biochemistry, 31, 1532, 10.1021/bi00120a034

van Tilbeurgh, 1993, Interfacial activation of the lipase–procolipase complex by mixed micelles revealed by X-ray crystallography, Nature (London), 362, 814, 10.1038/362814a0

Grochulski, 1994, Analogs of reaction intermediates identify a unique substrate binding site in Candida rugosa lipase, Biochemistry, 33, 3494, 10.1021/bi00178a005

Ollis, 1992, The α/β hydrolase fold, Protein Eng., 5, 197, 10.1093/protein/5.3.197

Schrag, 1997, Lipases and the α/β fold, Vol. 284, 85

Cygler, 1992, Advances in structural understanding of lipases, Biotechnol. Genet. Eng. Rev., 10, 143, 10.1080/02648725.1992.10647887

Davis, 1990, Hepatic lipase: site-directed mutagenesis of a serine residue important for catalytic activity, J. Biol.Chem., 265, 6291, 10.1016/S0021-9258(19)39324-X

Feller, 1991, Nucleotide sequence of the lipase gene lip2 from the antarctic psychrotroph Moraxella TA144 and the site-specific mutagenesis of the conserved serine and histidine residues, DNA Cell Biol., 10, 381, 10.1089/dna.1991.10.381

Hilton, 1991, Studies on the reaction mechanism of a microbial lipase/acyltransferase using chemical modification and site-directed mutagenesis, J. Biol. Chem., 266, 997, 10.1016/S0021-9258(17)35273-0

Vernet, 1993, Cloning and expression of Geotrichum candidum lipase II gene in yeast: probing of the enzyme active site by site-directed mutagenesis, J. Biol. Chem., 268, 26212, 10.1016/S0021-9258(19)74302-6

Derewenda, 1992, The crystal and molecular structure of the Rhizomucor miehei triacyglycerol lipase at 1.9 Å resolution, J. Mol. Biol., 227, 818, 10.1016/0022-2836(92)90225-9

Bertolini, 1995, Expression and characterization of Geotrichum candidum lipase I gene: comparison of specificity profile with lipase II, Eur. J. Biochem., 228, 863, 10.1111/j.1432-1033.1995.0863m.x

Haas, 1995, Lipases of the genera Rhizopus and Rhizomucor: versatile catalysts in nature and the laboratory, 549

Huge-Jensen, 1988, Studies on free and immobilized lipases from Mucor miehei, J. Am. Oil Chem. Soc., 65, 905, 10.1007/BF02544508

Pederson, 1995, Studies of the fatty acid specificity of the lipase from Rhizomucor miehei toward 20:1n−9, 20:5n−3, 22:1n−9, and 22:6n−3, J. Am. Oil Chem. Soc., 72, 239, 10.1007/BF02638906

Joerger, 1994, Alteration of chain length selectivity of a Rhizopus delemar lipase through site-directed mutagenesis, Lipids, 29, 377, 10.1007/BF02537305

Klein, 1997, Altered acyl chain length specificity of Rhizopus delemar lipase through mutagenesis and molecular modeling, Lipids, 32, 123, 10.1007/s11745-997-0016-1

Klein, 1997, Additive effects of acyl-binding site mutations on the fatty acid selectivity of Rhizopus delemar lipase, J. Am. Oil Chem. Soc., 74, 1401, 10.1007/s11746-997-0244-4

Atomi, 1995, Microbial lipases — from screening to design, 49

Schipper, 1984, A revision of the genus Rhizopus: 1. The Rhizopus stolonifer group and Rhizopus oryzae — Rhizopus Ehrenb. is revised, Stud. Mycol., 25, 1

Derewenda, 1994, Conformational lability of lipases observed in the absence of an oil–water interface: crystallographic studies of enzymes from the fungi Humicola lanuginosa and Rhizopus delemar, J. Lipid Res., 35, 524, 10.1016/S0022-2275(20)41203-9

Lawson, 1994, Probing the nature of substrate binding in Humicola lanuginosa lipase through X-ray crystallography and intuitive modeling, Protein Eng., 7, 543, 10.1093/protein/7.4.543

Holmquist, 1994, Trp89 in the lid of Humicola lanuginosa lipase is important for efficient hydrolysis of tributyrin, Lipids, 29, 599, 10.1007/BF02536093

Martinelle, 1996, The role of Glu87 and Trp89 in the lid of Humicola lanuginosa lipase, Protein Eng., 9, 519, 10.1093/protein/9.6.519

A. Svendsen, S. Patkar, M. Egel-Mitani, K. Borch, I.G. Clausen, M. Hansen, C. antarctica lipase and lipase variants. International Publication WO 94/01541, 1994.

Holmquist, 1993, Lipases from Rhizomucor miehei and Humicola lanuginosa: modification of the lid covering the active site alters enantioselectivity, J. Protein Chem., 12, 749, 10.1007/BF01024933

A. Svendson, I.G. Clausen, S. Patkar, E. Gormsen, Lipase variants, International Publication WO 92/05249, 1992.

Cygler, 1993, Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases and related proteins, Protein, 2, 366, 10.1002/pro.5560020309

Schrag, 1991, Ser–His–Glu triad forms the catalytic site of the lipase from Geotrichum candidum, Nature (London), 351, 761, 10.1038/351761a0

Grochulski, 1993, Insights into interfacial activation from an open structure of Candida rugosa lipase, J. Biol. Chem., 268, 12843, 10.1016/S0021-9258(18)31464-9

Grochulski, 1994, Two conformational states of Candida rugosa lipase, Protein Sci., 3, 82, 10.1002/pro.5560030111

Jensen, 1965, Specificity of a lipase from Geotrichum candidum for cis-octadecenoic acid, J. Am. Oil Chem. Soc., 42, 1029, 10.1007/BF02636897

D.A. Oester, A.L. Hall, S.J. Vesper, Enzymes produced by mutants of Geotrichum candida, International Publication WO 94/02587, 1994.

Shimada, 1989, cDNA molecular cloning of Geotrichum candidum lipase, J. Biochem., 106, 383, 10.1093/oxfordjournals.jbchem.a122862

Shimada, 1990, cDNA cloning and characterization of Geotrichum candidum lipase II, J. Biochem., 107, 703, 10.1093/oxfordjournals.jbchem.a123112

Holmquist, 1997, Identification of residues essential for differential fatty acyl specificity of Geotrichum candidum lipases I and II, Biochemistry, 36, 15019, 10.1021/bi971390d

Bott, 1994, Protein engineering of lipases, 337

M.V. Arbige, D.A. Estell, M.J. Pepsin, A.J. Poulose, Preparation of enzymes having altered activity, European Patent Application EP 0 260 105, 1988.

A.J. Poulose, S.A. Anderson, Enzymatic peracid bleaching system with modified enzyme. US Patent 5,108,457, 1992.

Boston, 1997, Structure and function of engineered Pseudomonas mendocina lipase, Vol. 284, 298

Kuipers, 1989, Enhanced activity and altered specificity of phospholipase A2 by deletion of a surface loop, Science, 244, 82, 10.1126/science.2704992

Thunnissen, 1990, Structure of an engineered porcine phospholipase A2 with enhanced activity at 2.1 Å resolution: comparison with the wild-type porcine and Crotalus atrox phospholipase A2, J. Mol. Biol., 216, 425, 10.1016/S0022-2836(05)80332-8

Laboureur, 1964, Properties of a highly active fungal lipase, Compt. Rend., 259, 4394

Haas, 1995, The enzymatic hydrolysis of triglyceride–phospholipid mixtures in an organic solvent, J. Am. Oil Chem. Soc., 72, 519, 10.1007/BF02638851

Davis, 1992, Chimeras of hepatic lipase and lipoprotein lipase, J. Biol. Chem., 267, 21499, 10.1016/S0021-9258(19)36637-2

van Oort, 1989, Purification and substrate specificity of Staphylococcus hyicus lipase, Biochemistry, 28, 9278, 10.1021/bi00450a007

Simons, 1996, The lipase from Staphylococcus aureus: expression in Escherichia coli, large-scale purification and comparison of substrate specificity to Staphylococcus hyicus lipase, Eur. J. Biochem., 242, 760, 10.1111/j.1432-1033.1996.0760r.x

Simons, 1998, Cloning, purification and characterization of the lipase from Staphylococcus epidermidis. Comparison of the substrate selectivity with those of other microbial lipases, Eur. J. Biochem., 253, 675, 10.1046/j.1432-1327.1998.2530675.x

Slotboom, 1973, Simplified pathways for the preparation of some well-defined phosphoglycerides, Chem. Phys. Lipids, 11, 295, 10.1016/0009-3084(73)90067-4

K.B. Pedersen, Hydrolysis of phospholipids using immobilized lipase, International Publication WO 91/03565, 1991.

O. Chmiel, N. Melachouris, H. Traitler, Procede d'interesterification de phospholipides, European Patent Application EP 0 739 985 A2, 1996.

Svensson, 1992, Lipase-catalyzed transesterification of phosphatidylcholine at controlled water activity, J. Am. Oil Chem. Soc., 69, 981, 10.1007/BF02541063

Svensson, 1990, Interesterification of phosphatidylcholine with lipases in organic media, Appl. Microbiol. Biotechnol., 33, 255, 10.1007/BF00164517

Mustranta, 1995, Comparison of lipases and phospholipases in the hydrolysis of phospholipids, Process Biochem., 30, 393, 10.1016/0032-9592(94)00030-1

Sarney, 1994, Lipase-catalyzed synthesis of lysophospholipids in a continuous bioreactor, J. Am. Oil Chem. Soc., 71, 93, 10.1007/BF02541478

Beer, 1996, The folding and activity of the extracellular lipase of Rhizopus oryzae are modulated by a prosequence, Biochem. J., 319, 351, 10.1042/bj3190351

Chaillan, 1992, Direct involvement of the C-terminal extremity of pancreatic lipase (403–449) in colipase binding, Biochem. Biophys. Res. Commun., 184, 206, 10.1016/0006-291X(92)91179-T

Lohse, 1997, Human lysosomal acid lipase/cholesteryl ester hydrolase and human gastric lipase: site-directed mutagenesis of Cys227 and Cys236 results in substrate-dependent reduction of enzymatic activity, J. Lipid Res., 38, 1896, 10.1016/S0022-2275(20)37164-9

A.M. Batenburg, M.R. Egmond, L.G.J. Frenken, Enzymes and enzymatic detergent compositions, European Patent Application EP 0 407 225 A1, 1990.

M.M.J. Cox, H.B.M. Lenting, L.J.S. Mulleners, J.M. Van Der Laan, Modified Pseudomonas lipase with 21 methionine replaced- and related DNA, vectors and transformed cells, useful in detergent compositions with improved wash performance, oxidative stability, etc., International Publication WO 94/25578, 1994.

Patkar, 1997, Effect of mutation in non-consensus sequence Thr–X–Ser–X–Gly of Candida antarctica lipase B on lipase specificity, specific activity and thermostability, J. Mol. Catal. B: Enzymatic, 3, 51, 10.1016/S1381-1177(96)00036-7

Cadwell, 1992, Randomization of genes by PCR mutagenesis, PCR Meth. Appl., 2, 28, 10.1101/gr.2.1.28

Shinkai, 1996, Substitutions of Ser for Asn-163 and Pro for Leu-264 are important for stabilization of lipase from Pseudomonas aeruginosa, J. Biochem., 120, 915, 10.1093/oxfordjournals.jbchem.a021506

L.G.J. Frenken, H. Peters, H.M.U. Suerbaum, J. De Vlieg, C.T. Verrips, Modified Pseudomonas lipases and their use, International Publication WO 95/35381, 1995.

J.S. Okkels, A. Svendsen, K. Borch, M. Thellersen, S.A. Patkar, D.A. Petersen, J.C. Royer, T. Kretzschmar, Novel lipolytic enzymes, International Publication WO 97/07202, 1997.

W. Aehle, G. Gerritse, H.B.M. Lenting, Lipases with improved surfactant resistance, International Publication WO 95/30744, 1995.

L.G. Frenken, H. Peters, H.M.U. Suerbaum, J. DeVlieg, C.T. Verrips, Modified Pseudomonas lipases and their use, International Publication WO 96/00292, 1996.

A. Svendsen, I.G. Clausen, H.S. Okkels, M. Thellersen, A method of preparing a variant of a lipolytic enzyme, International Publication WO 95/22615, 1995.

C.C. Fuglsang, J.S. Okkels, D.A. Pertersen, S.A. Patkar, M. Thellersen, J. Vind, T. Halkier, S.T. Jørgersen, A modified enzyme with lipolytic activity, International Publication WO 97/04078, 1997.

Joerger, 1993, Overexpression of a Rhizopus delemar lipase gene in Escherichia coli, Lipids, 28, 81, 10.1007/BF02535769

Cousin, 1996, A cholinesterase genes server (ESTHER): a database of cholinesterase-related sequences for multiple alignments, phylogenetic relationships, mutations and structural data retrieval, Nucleic Acids Res., 24, 132, 10.1093/nar/24.1.132

Arnold, 1996, Directed Evolution: creating biocatalysts for the future, Chem. Eng. Sci., 51, 5091, 10.1016/S0009-2509(96)00288-6

Reetz, 1997, Creation of enantioselective biocatalysts for organic chemistry by in vitro evolution, Angew. Chem. Int. Ed. Engl., 36, 2830, 10.1002/anie.199728301

Moore, 1997, Strategies for the in vitro evolution of protein function — enzyme evolution by random recombination of improved sequences, J. Mol. Biol., 272, 336, 10.1006/jmbi.1997.1252

Shao, 1998, Random-priming in vitro recombination — an effective tool for directed evolution, Nucleic Acids Res., 26, 681, 10.1093/nar/26.2.681

Zhao, 1998, Molecular evolution by staggered extension process (STEP) in vitro recombination, Nat. Biotechnol., 16, 258, 10.1038/nbt0398-258

Moore, 1996, Directed evolution of a para-nitrobenzyl esterase for aqueous-organic solvents, Nat. Biotechnol., 14, 458, 10.1038/nbt0496-458