How is the reactivity of laccase affected by single-point mutations? Engineering laccase for improved activity towards sterically demanding substrates

Applied Microbiology and Biotechnology

Volumn 91, Issue 1, 2011, Pages 123-131

  Galli, Carlo ^a   Gentili, Patrizia ^a   Jolivalt, Claude ^b   Madzak, Catherine ^c   Vadalà, Raffaella ^a,b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b PSL RESEARCH UNIVERSITY   (France)

^c UMR1319 MICALIS   (France)

Author keywords

Active site; Laccase; Oxidation reactivity; Site directed mutagenesis; Steric hindrance

Indexed keywords

ACTIVE SITE; LACCASES; OXIDATION REACTIVITY; SITE DIRECTED MUTAGENESIS; STERIC HINDRANCES;

AMINO ACIDS; CRYSTAL STRUCTURE; ETHERS; HYDROPHOBICITY; MUTAGENESIS; OXIDATION; PHENOLS; THERMODYNAMIC STABILITY;

SUBSTRATES;

4,4' ISOPROPYLIDENEDIPHENOL; ALANINE; LACCASE; MUTANT PROTEIN; PHENOL; PHENYLALANINE;

AMINO ACID; BIOENGINEERING; CRYSTAL STRUCTURE; ENZYME ACTIVITY; HYDROPHOBICITY; MUSHROOM; MUTATION; OXIC CONDITIONS; OXIDATION; PHENOL; SHELL; SUBSTRATE;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; CHEMICAL INTERACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME METABOLISM; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; HYDROPHOBICITY; MOLECULAR DOCKING; NONHUMAN; PROTEIN EXPRESSION; SITE DIRECTED MUTAGENESIS; WILD TYPE;

AMINO ACID SEQUENCE; BINDING SITES; FUNGAL PROTEINS; GENE EXPRESSION; KINETICS; LACCASE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; PHENOLS; POINT MUTATION; PROTEIN ENGINEERING; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TRAMETES; YARROWIA;

TRAMETES VERSICOLOR;

EID: 79959212575     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3240-4     Document Type: Article

References (32)

1. Aweke Tadesse M, D'Annibale A, Galli C, Gentili P, Sergi F (2008) An assessment of the relative contributions of redox and steric issues to laccase specificity towards putative substrates. Org Biomol Chem 6:868-878 (Pubitemid 351653357)
2. Baldrian P (2006) Fungal laccases - occurrence and properties. FEMS Microbiol Rev 30:215-242
3. Bertrand T, Jolivalt C, Briozzo P, Caminade E, Joly N, Madzak C, Mougin C (2002) Crystal structure of a four-copper laccase complexed with an arylamine: insights into substrate recognition and correlation with kinetics. Biochemistry 41:7325-7333 (Pubitemid 34602449)
4. Camarero S, Ibarra D, Martínez AT (2007) Paper pulp delignification using laccase and natural mediators. Enzyme Microbiol Technol 40:1264-1271 (Pubitemid 46371320)
5. Choinowski T, Antorini M, Piontek K (2002) Crystal structure of a laccase from the fungus Trametes versicolor at 1.90-Å resolution containing a full complement of coppers. J Biol Chem 277:37663-37669
6. d'Acunzo F, Galli C, Gentili P, Sergi F (2006) Mechanistic and steric issues in the oxidation of phenolic and non-phenolic compounds by laccase or laccase-mediator systems. The case of bifunctional substrates. New J Chem 30:583-591
7. d'Acunzo F, Barreca AM, Galli C (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 31:25-30
8. DeLano WL (2002) PyMol. DeLano Scientific, San Carlos
9. Enguita FJ, Marçal D, Martins LO, Grenha R, Henriques AO, Lindley PF, Carrondo MA (2004) Substrate and dioxygen binding to the endospore coat laccase from Bacillus subtilis. J Biol Chem 279:23472-23476
10. Gianfreda L, Xu F, Bollag J-M (1999) Laccases: a useful group of oxidoreductive enzymes. Bioremediat J 3:1-25
11. Giardina P, Faraco V, Pezzella C, Piscitelli A, Vanhulle S, Sannia G (2010) Laccases: a never-ending story. Cell Mol Life Sci 67:369-385
12. Jolivalt C, Madzak C, Brault A, Caminade E, Malosse C, Mougin C (2005) Expression of laccase IIIb from the white-rot fungus Trametes versicolor in the yeast Yarrowia lipolytica for environmental applications. Appl Microbiol Biotechnol 66:450-456 (Pubitemid 40110152)
13. Jönsson L, Sjöström K, Häggstrom I, Nyman PO (1995) Characterization of a laccase gene from the white-rot fungus Trametes versicolor and structural features of basidiomycete laccases. Biochim Biophys Acta 1251:210-215
14. Kallio JP, Hakulinen N, Rouvinen J (2009) Structure function studies of a Melanocarpus albomyces laccase suggest a pathway for oxidation of phenolic compounds. J Mol Biol 392:895-909
15. Koschorreck K, Richter SM, Swierczek A, Beifuss U, Schmid RD, Urlacher VB (2008) Comparative characterization of four laccases from Trametes versicolor concerning phenolic C-C coupling and oxidation of PAHs. Arch Biochem Biophys 474:213-219
16. Le Dall MT, Nicaud JM, Gaillardin C (1994) Multiple-copy integration in the yeast Yarrowia lipolytica. Curr Genet 26:38-44
17. Madzak C, Gaillardin C, Beckerich J-M (2004) Heterologous protein expression and secretion in the non-conventional yeast Yarrowia lipolytica: a review. J Biotechnol 109:63-81 (Pubitemid 38452572)
18. Madzak C, Mimmi MC, Caminade E, Brault A, Baumberger S, Briozzo P, Mougin C, Jolivalt C (2006) Shifting the optimal pH of activity for a laccase from the fungus Trametes versicolor by structure-based mutagenesis. Protein Eng Des Sel 19:77-84 (Pubitemid 43162259)
19. Matera I, Gullotto A, Tilli S, Ferraroni M, Scozzafava A, Briganti F (2008) Crystal structure of the blue multicopper oxidase from the white-rot fungus Trametes trogii complexed with p-toluate. Inorg Chim Acta 361:4129-4137
20. Messerschmidt A (1997) Multi-copper oxidases. World Scientific, Singapore
21. Mohamad SB, Ong AL, Ripen AM (2008) Evolutionary trace analysis at the ligand binding site of laccase. Bioinformation 2:369-372
22. Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE (2004) UCSF chimera - a visualization system for exploratory research and analysis. J Comput Chem 25:1605-1612
23. Rodríguez Couto S, Toca Herrera JL (2006) Industrial and biotechnological applications of laccases: a review. Biotechnol Adv 24:500-513 (Pubitemid 44082015)
24. Sivropoulou A, Papanikolaou E, Nikolaou C, Kokkini S, Lanaras T, Arsenakis M (1996) Antimicrobial and cytotoxic activities of origanum essential oils. J Agr Food Chem 44:1202-1205 (Pubitemid 126467844)
25. Solomon EI, Sundaram UM, Machonkin TE (1996) Multicopper oxidases and oxygenases. Chem Rev 96:2563-2606
26. Suatoni JC, Snyder RE, Clark RO (1961) Voltammetric studies of phenol and aniline ring substitution. Anal Chem 33:1894-1897
27. Thurston CF (1994) The structure and function of fungal laccases. Microbiology 140:19-26
28. Widsten P, Kandelbauer A (2008) Laccase applications in the forest products industry: a review. EnzymeMicrobiol Technol 42:293-307
29. Xu F (1996) Oxidation of phenols, anilines, and benzenethiols by fungal laccases: correlation between activity and redox potentials as well as halide inhibition. Biochemistry 35:7608-7614
30. Xu F, Shin W, Brown SH, Wahleithner JA, Sundaram UM, Solomon EI (1996) A study of a series of recombinant fungal laccases and birilubin oxidase that exhibit significant differences in redox potential, substrate specificity and stability. Biochim Biophys Acta 1292:303-311 (Pubitemid 26071166)
31. Yanagisawa S, Crowley PB, Firbank SJ, Lawler AT, Hunter DM, McFarlane W, Li C, Kohzuma T, Banfield MJ, Dennison C (2008) π-Interaction tuning of the active site properties of metalloproteins. J Am Chem Soc 130:15420-15428
32. Yaver DS, Xu F, Golightly EJ, Brown KM, Brown SH, Rey MW, Schneider P, Halkier T, Mondorf K, Dalbøge H (1996) Purification, characterization, molecular cloning, and expression of two laccase genes from the white rot basidiomycete Trametes villosa. Appl Environ Microbiol 62:834-841 (Pubitemid 26074180)