In Vitro Evolution of a Fungal Laccase in High Concentrations of Organic Cosolvents

Chemistry & Biology - Tập 14 - Trang 1052-1064 - 2007
Miren Zumárraga1, Thomas Bulter2, Sergey Shleev3, Julio Polaina4, Arturo Martínez-Arias1, Francisco J. Plou1, Antonio Ballesteros1, Miguel Alcalde1
1Department of Biocatalysis, Institute of Catalysis, Consejo Superior de Investigaciones Cientificas, Cantoblanco, 28049 Madrid, Spain
2Gevo, Incorporated, Pasadena, CA 91107, USA
3Department of Analytical Chemistry, Lund University, 22100 Lund, Sweden
4Institute of Agrochemistry and Food Technology, Consejo Superior de Investigaciones Cientificas, Paterna, 46980 Valencia, Spain

Tài liệu tham khảo

Alcalde, 2006, Environmental biocatalysis: from remediation with enzymes to novel green processes, Trends Biotechnol., 24, 281, 10.1016/j.tibtech.2006.04.002 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 Ogino, 2001, Enzymes which are stable in the presence of organic solvents, J. Biosci. Bioeng., 91, 109, 10.1016/S1389-1723(01)80051-7 Arnold, 1990, Engineering enzymes for nonaqueous solvents, Trends Biotechnol., 8, 244, 10.1016/0167-7799(90)90186-2 Riva, 2006, Laccase: blue enzymes for green chemistry, Trends Biotechnol., 24, 219, 10.1016/j.tibtech.2006.03.006 Xu, 2005, Applications of oxidoreductases: recent progress, Ind. Biotechnol., 1, 38, 10.1089/ind.2005.1.38 Alcalde, 2002, Colorimetric assays for biodegradation of polycyclic aromatic hydrocarbons by fungal laccases, J. Biomol. Screen., 7, 547, 10.1177/1087057102238629 Alcalde, 2007, Laccase: biological functions, molecular structure and industrial applications, 459 Bourbonnais, 1990, Oxidation of nonphenolic substrates—an expanded role for laccase in lignin biodegradation, FEBS Lett., 267, 99, 10.1016/0014-5793(90)80298-W Torres, 2003, Potential use of oxidative enzymes for the detoxification of organic pollutants, Appl. Catal. B Environ., 46, 1, 10.1016/S0926-3373(03)00228-5 Karamyshev, 2003, Laccase-catalyzed synthesis of conducting polyaniline, Enzyme Microb. Technol., 33, 556, 10.1016/S0141-0229(03)00163-7 Baldrian, 2006, Fungal laccases—occurrence and properties, FEMS Microbiol. Rev., 30, 215, 10.1111/j.1574-4976.2005.00010.x Alcalde, 2005, Screening mutant libraries of fungal laccases in the presence of organic solvents, J. Biomol. Screen., 10, 624, 10.1177/1087057105277058 d'Acunzo, 2004, Determination of the activity of laccase, and mediated oxidation of a lignin model compound, in aqueous-organic mixed solvents, J. Mol. Catal., B Enzym., 31, 25, 10.1016/j.molcatb.2004.07.001 Rodakiewicz-Nowak, 2000, Effect of various water-miscible solvents on enzymatic activity of fungal laccases, J. Mol. Catal., B Enzym., 11, 1, 10.1016/S1381-1177(00)00183-1 Bulter, 2003, Functional expression of a fungal laccase in Saccharomyces cerevisiae by directed evolution, Appl. Environ. Microbiol., 69, 987, 10.1128/AEM.69.2.987-995.2003 Bloom, 2006, Protein stability promotes evolvability, Proc. Natl. Acad. Sci. USA, 103, 5869, 10.1073/pnas.0510098103 Bulter, 2003, Preparing libraries in Saccharomyces cerevisiae, 17 Cherry, 1999, Directed evolution of a fungal peroxidase, Nat. Biotechnol., 17, 379, 10.1038/7939 Alcalde, 2006, Combinatorial saturation mutagenesis by in vivo overlap extension for the engineering of fungal laccases, Comb. Chem. High T. Scr., 9, 719 Madzak, 2006, Shifting the optimal pH of activity for a laccase from the fungus Trametes versicolor by structure-based mutagenesis, Protein Eng. Des. Sel., 19, 77, 10.1093/protein/gzj004 Shleev, 2004, Comparison of physico-chemical characteristics of four laccases from different basidiomycetes, Biochimie, 86, 693, 10.1016/j.biochi.2004.08.005 Xu, 1998, Site-directed mutations in fungal laccase: effect on redox potential, activity and pH profile, Biochem. J., 334, 63, 10.1042/bj3340063 Xu, 1999, Targeted mutations in a Trametes villosa laccase. Axial perturbations of the T1 copper, J. Biol. Chem., 274, 12372, 10.1074/jbc.274.18.12372 Palmer, 2003, Spectroscopy characterization of the Leu513His variant of fungal laccase: effect of increased axial ligand interaction on the geometric and electronic structure of the type 1 Cu site, Inorg. Chem., 42, 4006, 10.1021/ic026099n Shleev, 2005, Direct electron transfer reactions of laccases from different origins on carbon electrodes, Bioelectrochemistry, 67, 115, 10.1016/j.bioelechem.2005.02.004 Shleev, 2005, Direct electron transfer between copper-containing proteins and electrodes, Biosens. Bioelectron., 20, 2517, 10.1016/j.bios.2004.10.003 Shleev, 2005, Electrochemical redox transformations of T1 and T2 copper sites in native Trametes hirsuta laccase at gold electrode, Biochem. J., 385, 745, 10.1042/BJ20041015 Pita, 2006, Direct heterogeneous electron transfer reactions of fungal laccases at bare and thiol-modified gold electrodes, Electrochem. Commun., 8, 747, 10.1016/j.elecom.2006.03.008 Shleev, 2006, Direct heterogeneous electron transfer reactions of Trametes hirsuta laccase at bare and thiol-modified gold electrodes, Electroanalysis, 18, 1901, 10.1002/elan.200603600 Kiiskinen, 2004, Molecular cloning and expression in Saccharomyces cerevisiae of a laccase gene from the ascomycete Melanocarpus albomyces, Appl. Environ. Microbiol., 70, 137, 10.1128/AEM.70.1.137-144.2004 Hakulinen, 2002, Crystal structure of a laccase from Melanocarpus albomyces with an intact trinuclear copper site, Nat. Struct. Biol., 9, 601 Lopez Camacho, 1996, Amino acid substitution enhancing thermostability of Bacillus polymixa β-glucosidase A, Biochem. J., 314, 833, 10.1042/bj3140833 Shuster, 1991, Gene expression in yeast: protein secretion, Curr. Opin. Biotechnol., 2, 685, 10.1016/0958-1669(91)90035-4 Germann, 1988, Characterization of two allelic forms of Neurospora crassa laccase. Amino-terminal and carboxyl-terminal processing of a precursor, J. Biol. Chem., 263, 885, 10.1016/S0021-9258(19)35436-5 Wong, 2004, Laboratory evolution of cytochrome P450BM-3 monooxygenase for organic cosolvents, Biotechnol. Bioeng., 85, 351, 10.1002/bit.10896 Rai, 2001, Directed evolution of chloroperoxidase for improved epoxidation and chlorination catalysis, Adv. Synth. Catal., 343, 638, 10.1002/1615-4169(200108)343:6/7<638::AID-ADSC638>3.0.CO;2-6 Roccatano, 2005, Structural and dynamic properties of cytochrome P450BM-3 in pure water and in a dimethylsulfoxide/water mixture, Biopolymers, 78, 259, 10.1002/bip.20290 Bogdanovskaya, 2002, Peculiarities of direct bioelectrocatalysis by laccase in aqueous-nonaqueous mixtures, Biosens. Bioelectron., 17, 945, 10.1016/S0956-5663(02)00086-6 Bloom, 2004, Stability and the evolvability of function in a model protein, Biophys. J., 86, 2758, 10.1016/S0006-3495(04)74329-5 Rodakiewicz-Nowak, 2007, Catalytic activity of Cerrena unicolor laccase in aqueous solutions of water-miscible organic solvents. Experimental and numerical description, J. Mol. Catal., B Enzym., 44, 53, 10.1016/j.molcatb.2006.08.005 Zumárraga, 2007, Bioremediation of polycyclic aromatic hydrocarbons by fungal laccases engineered by directed evolution, Biocatal. Biotransformation, 26, 1 Roy, 2006, Preparation and characterization of cross-linked enzyme crystals of laccase, J. Mol. Catal., B Enzym., 38, 31, 10.1016/j.molcatb.2005.11.001 Vandertol-Vanier, 2002, Enhanced activity by poly(ethylene glycol) modification of Coriolopsis gallica laccase, J. Ind. Microbiol. Biotechnol., 29, 214, 10.1038/sj.jim.7000308 Okazaki, 2002, Oxidation of bisphenol A catalyzed by laccase hosted in reversed micelles in organic media, Enzyme Microb. Technol., 31, 227, 10.1016/S0141-0229(02)00104-7 Gercog, 1985 Larsson, 2001, Spectroelectrochemical study of cellobiose dehydrogenase and diaphorase in a thiol-modified gold capillary in the absence of mediators, Bioelectrochemistry, 53, 243, 10.1016/S0302-4598(01)00099-X Christenson, 2006, Redox potentials of the blue copper sites of bilirubin oxidases, Biochim. Biophys. Acta, 1757, 1634, 10.1016/j.bbabio.2006.08.008