Lipases as practical biocatalysts

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

Jaeger, 1999, Bacterial biocatalysts: molecular biology, three-dimensional structures, and biotechnological applications of lipases, Annu Rev Microbiol, 53, 315, 10.1146/annurev.micro.53.1.315

Villeneuve, 2000, Customizing lipases for biocatalysis: a survey of chemical, physical and molecular biological approaches, J Mol Catal B Enzym, 9, 113, 10.1016/S1381-1177(99)00107-1

Koeller, 2001, Enzymes for chemical synthesis, Nature, 409, 232, 10.1038/35051706

Schmid, 2001, Industrial biocatalysis today and tomorrow, Nature, 409, 258, 10.1038/35051736

Klibanov, 2001, Improving enzymes by using them in organic solvents, Nature, 409, 241, 10.1038/35051719

Akai S, Naka T, Fujita T, Takebe Y, Kita Y: 1-Ethoxyvinyl 2-furoate, an efficient acyl donor for the lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted propane-1,3-diols and meso-1,2-diols. Chem Commun 2000:1461-1462.

Lee, 2000, Enhancing the enantioselectivity of lipase in transesterification by substrate matching: an enzyme memory based approach, Org Lett, 2, 2553, 10.1021/ol0062897

Won, 2001, Computer-aided control of water activity for lipase-catalyzed esterification in solvent-free systems, Biotechnol Prog, 17, 258, 10.1021/bp000154i

Turner, 2000, At what temperature can enzymes maintain their catalytic activity?, Enzyme Microb Technol, 27, 108, 10.1016/S0141-0229(00)00184-8

López-Serrano, 2001, Enantioselective enzyme catalysed ammoniolysis of amino acid derivatives. Effect of temperature, Tetrahedron Asymmetry, 12, 235, 10.1016/S0957-4166(01)00023-4

Watanabe, 2001, Effects of substituent and temperature on enantioselectivity for lipase-catalyzed esterification of 2-(4-substituted phenoxy) propionic acids on organic solvents, Bioorg Chem, 29, 65, 10.1006/bioo.2000.1190

Cainelli G, De Matteis V, Galletti P, Giacomini D, Orioli P: Temperature and solvent effects on enzyme stereoselectivity: inversion temperature in kinetic resolutions with lipases. Chem Commun 2000:2351-2352. For the first time, an inversion temperature has been observed in an enzyme-catalyzed kinetic resolution, specifically in the lipase-catalyzed acylation of a chiral alcohol. The selectivity factor is highest at the inversion temperature of −42°C (E = 99), enantioselectivity at lower or higher temperatures being less pronounced.

Pencreach, 2001, Comparison of hydrolytic activity in water and heptane for thirty-two commercial lipase preparations, Enzyme Microb Technol, 28, 473, 10.1016/S0141-0229(00)00355-0

Matsumoto, 2001, Enhanced activities of lipase pretreated with organic solvents, J Chem Technol Biotechnol, 76, 1070, 10.1002/jctb.491

Carrea, 2000, Properties and synthetic applications of enzymes in organic solvents, Angew Chem Int Ed Engl, 39, 2226, 10.1002/1521-3773(20000703)39:13<2226::AID-ANIE2226>3.0.CO;2-L

Lau, 2000, Lipase-catalyzed reactions in ionic liquids, Org Lett, 2, 4189, 10.1021/ol006732d

Schöfer SH, Kaftzik N, Wasserscheid P, Kragl U: Enzyme catalysis in ionic liquids: lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselectivity. Chem Commun 2001:425-426.

Kim, 2001, Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase, Org Lett, 3, 1507, 10.1021/ol015824f

Itoh T, Akasaki E, Kudo K, Shirakami S: Lipase-catalyzed enantioselective acylation in the ionic liquid solvent system: reaction of enzyme anchored to the solvent. Chem Lett 2001:262-263.

Lozano, 2001, Over-stabilization of Candida antarctica lipase B by ionic liquids in ester synthesis, Biotechnol Lett, 23, 1529, 10.1023/A:1011697609756

Matsuda, 2001, Control on enantioselectivity with pressure for lipase-catalyzed esterification in supercritical carbon dioxide, Tetrahedron Lett, 42, 8319, 10.1016/S0040-4039(01)01785-3

Liu, 2000, Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester, J Mol Catal B Enzym, 10, 523, 10.1016/S1381-1177(00)00093-X

Okamoto, 2000, A new method for improving the enantioselectivity of lipase-catalyzed hydrolysis in organic solvent containing a small amount of water in the presence of metal ions, Biotechnol Lett, 22, 1169, 10.1023/A:1005637329704

Quirós, 2001, Tuning lipase enantioselectivity in organic media using solid-state buffers, J Org Chem, 66, 5074, 10.1021/jo0101104

Shin, 2000, Improving lipase enantioselectivity in organic solvents by forming substrate salts with chiral agents, Biotechnol Bioeng, 69, 577, 10.1002/1097-0290(20000905)69:5<577::AID-BIT12>3.0.CO;2-Y

Vedejs, 2001, Parallel kinetic resolution under catalytic conditions: a three-phase system allows selective reagent activation using two catalysts, J Am Chem Soc, 123, 2428, 10.1021/ja0035405

Palekar, 2000, Purification of lipase: a review, Biocatal Biotransform, 18, 177, 10.3109/10242420009015244

Reetz MT, Wenkel R, Avnir D: Entrapment of lipases in hydrophobic sol-gel-materials: efficient heterogeneous biocatalysts in aqueous medium. Synthesis 2000:781-783.

Vaghjiani, 2000, Production and characterisation of cross-linked enzyme crystals (CLECs®) for application as process scale biocatalysts, Biocatal Biotransform, 18, 151, 10.3109/10242420009015243

Persson, 2000, Immobilisation of lipases by adsorption and deposition: high protein loading given lower water activity optimum, Biotechnol Lett, 22, 1571, 10.1023/A:1005689002238

Guisan, 2001, Preparation of new lipases derivatives with high activity-stability in anhydrous media: adsorption on hydrophobic supports plus hydrophilization with polyethylenimine, J Mol Catal B Enzym, 11, 817, 10.1016/S1381-1177(00)00011-4

Schuleit, 2001, Enzyme immobilization in silica-hardened organogels, Biotechnol Bioeng, 72, 249, 10.1002/1097-0290(20000120)72:2<249::AID-BIT13>3.0.CO;2-B

Pierre, 2001, Influence of the porous texture of silica gels on the enzymatic activity of lipases in esterification reactions, J Mol Catal B Enzym, 11, 639, 10.1016/S1381-1177(00)00083-7

Shibatani, 2000, Enzymatic resolution of diltiazem intermediate by Serratia marcescens lipase: molecular mechanism of lipase secretion and its industrial application, J Mol Catal B: Enzym, 10, 141, 10.1016/S1381-1177(00)00122-3

Gascoyne, 2001, 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, J Org Chem, 66, 3041, 10.1021/jo005681v

Ottosson, 2001, Rational design of enantioselective enzymes requires considerations of entropy, Protein Sci, 10, 1769, 10.1110/ps.13501

Kovac A, Scheib H, Pleiss J, Schmid RD, Paltauf F: Molecular basis of lipase stereoselectivity, Eur J Lipid Sci Technol 2000:61-77. This excellent article illuminates the origin of stereoselectivity of lipase-catalyzed reactions, reviewing qualitative models such as the Kazlauskas rules and other empirical guidelines. Included are also recent information of enzyme–substrate complexes as studied by X-ray and NMR analysis.

Tafi, 2000, Computer simulations of enantioselective ester hydrolyses catalyzed by Pseudomonas cepacia lipase, J Org Chem, 65, 3659, 10.1021/jo9919198

Petersen, 2001, How do lipases and esterases work: the electrostatic contribution, J Biotechnol, 85, 115, 10.1016/S0168-1656(00)00360-6

Svendsen, 2000, Lipase protein engineering, Biochim Biophys Acta, 1543, 223, 10.1016/S0167-4838(00)00239-9

Magnusson, 2001, Creation of an enantioselective hydrolase by engineered substrate-assisted catalysis, J Am Chem Soc, 123, 4354, 10.1021/ja015604x

Rotticci, 2001, Improved enantioselectivity of a lipase by rational protein engineering, ChemBioChem, 2, 766, 10.1002/1439-7633(20011001)2:10<766::AID-CBIC766>3.0.CO;2-K

Arnold, 2001, Combinatorial and computational challenges for biocatalyst design, Nature, 409, 253, 10.1038/35051731

Powell, 2001, Directed evolution and biocatalysis, Angew Chem Int Ed Engl, 40, 3948, 10.1002/1521-3773(20011105)40:21<3948::AID-ANIE3948>3.0.CO;2-N

Reetz, 2001, Directed evolution of an enantioselective enzyme through combinatorial multiple-cassette mutagenesis, Angew Chem Int Ed Engl, 40, 3589, 10.1002/1521-3773(20011001)40:19<3589::AID-ANIE3589>3.0.CO;2-X

Reetz, 2001, Combinatorial and evolution-based methods in the creation of enantioselective catalysts, Angew Chem Int Ed Engl, 40, 284, 10.1002/1521-3773(20010119)40:2<284::AID-ANIE284>3.0.CO;2-N

van Kampen, 2000, Directed evolution: from a staphylococcal lipase to a phospholipase, Eur J Lipid Sci Technol, 102, 717, 10.1002/1438-9312(200012)102:12<717::AID-EJLT717>3.0.CO;2-Z

Huerta, 2000, Dynamic kinetic resolution of α-hydroxy acid esters, Organic Lett, 2, 1037, 10.1021/ol000014+

Liu, 2000, Chemoenzymatic construction of a four-component Ugi combinatorial library, Biotechnol Bioeng, 69, 457, 10.1002/1097-0290(20000820)69:4<457::AID-BIT12>3.0.CO;2-L

Tan, 2001, The synthesis of (+)-allopumiliotoxin 323B′, Chem Eur J, 7, 1845, 10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

Brenna E, Fuganti C, Grasselli P, Serra S: Enzyme-mediated synthesis of (S)- and (R)-verapamil. Eur J Org Chem 2001:1349-1357.

Held, 2001, Enantioselective synthesis of the ricciocarpins A and B, Angew Chem Int Ed Engl, 40, 1058, 10.1002/1521-3773(20010316)40:6<1058::AID-ANIE10580>3.0.CO;2-3

Córdova, 2001, A highly chemo- and stereoselective synthesis of β-keto esters via a polymer-supported lipase catalyzed transesterification, J Org Chem, 66, 1906, 10.1021/jo001478o

Hieber, 2001, Introducing ChiPros™-biocatalytic production of chiral intermediates on a commercial scale, Chim Oggi, 19, 16

Morgan, 2000, Enzymatic kinetic resolution of piperidine atropisomers: synthesis of a key intermediate of the farnesyl protein transferase inhibitor, SCH66336, J Org Chem, 65, 5452, 10.1021/jo991513v

Wirz, 2000, Multiselective enzymatic reactions for the synthesis of protected homochiral cis- and trans-1,3,5-cyclohexanetriols, Tetrahedron Asymmetry, 11, 4171, 10.1016/S0957-4166(00)00368-2

Matsubara, 2001, An efficient synthesis of optical isomers of vasopressin V2 receptor antagonist OPC-41061 by lipase-catalyzed enantioselective transesterification, Heterocycles, 54, 131, 10.3987/COM-99-S(I)2

Hanson, 2000, Regioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug, Bioorg Med Chem, 8, 2681, 10.1016/S0968-0896(00)00209-1

Gum, 2000, Enyzme-labile protecting groups in peptide synthesis: development of glucose- and galactose-derived urethanes, Chem Eur J, 6, 3714, 10.1002/1521-3765(20001016)6:20<3714::AID-CHEM3714>3.0.CO;2-Z

Pesti, 2001, Reversible Michael-enzymatic hydrolysis: a new variant of dynamic resolution, J Am Chem Soc, 123, 11075, 10.1021/ja011811l