First evidence of catalytic mediation by phenolic compounds in the laccase-induced oxidation of lignin models

European Journal of Biochemistry

Volumn 270, Issue 17, 2003, Pages 3634-3640

  D'Acunzo, Francesca ^b   Galli, Carlo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b NONE

Author keywords

Acidity; Laccase; Lignin models; Phenolic mediators; Radicals

Indexed keywords

2,4,6 TRI TERT BUTYLPHENOL; 4 METHOXYBENZYL ALCOHOL; ALCOHOL DERIVATIVE; LACCASE; LIGNIN; PHENOL DERIVATIVE; PHENOLSULFONPHTHALEIN; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL STRUCTURE; COMPARATIVE STUDY; CYCLIC POTENTIOMETRY; DEGRADATION; ENZYME ACTIVE SITE; MOLECULAR MODEL; NONHUMAN; OXIDATION; PH; PRIORITY JOURNAL; PROTON TRANSPORT; STRUCTURE ANALYSIS;

3-HYDROXYANTHRANILIC ACID; ANISOLES; BASIDIOMYCOTA; BENZOQUINONES; CATALYSIS; ELECTROCHEMISTRY; FREE RADICALS; HYDROGEN-ION CONCENTRATION; ISOMERISM; KINETICS; LACCASE; LIGNIN; MASS SPECTROMETRY; OXIDATION-REDUCTION; OXIDOREDUCTASES; PHENOLS; PHENOLSULFONPHTHALEIN; TRIAZOLES;

EID: 0041322839     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1033.2003.03752.x     Document Type: Article

References (30)

1. ten Have, R. & Teunissen, P.J.M. (2001) Oxidative mechanisms involved in lignin degradation by white-rot fungi. Chem. Rev. 101, 3397-3413.
2. Böhmer, S., Messner, K. & Srebotnik, E. (1998) Oxidation of phenanthrene by a fungal laccase in the presence of 1-hydroxy-benzotriazole and unsaturated lipids. Biochem. Biophys. Res. Commun. 244, 233-238.
3. Thurston, C.F. (1994) The structure and function of fungal laccases. Microbiology 140, 19-26.
4. Srebotnik, E., Jensen, K.A. Jr & Hammel, K.E. (1994) Fungal degradation of recalcitrant non-phenolic lignin structures without lignin peroxidase. Proc. Natl Acad. Sci. USA 91, 12794-12797.
5. Kapich, A.N., Hofrichter, M., Vares, T. & Hatakka, A. (1999) Coupling of manganese peroxidase-mediated lipid peroxidation with destruction of nonphenolic lignin model compounds and 14C-labeled lignins. Biochem. Biophys. Res. Commun. 259, 212-219.
6. Itoh, K., Fujita, M., Kumano, K., Suyama, K. & Yamamoto, H. (2000) Phenolic acids affect transformations of chlorophenols by a Coriolus versicolor laccase. Soil Biol. Biochem. 32, 85-91.
7. Johannes, C. & Majcherczyk, A. (2000) Natural mediators in the oxidation of polycyclic aromatic hydrocarbons by laccase mediator systems. Appl. Environ. Microbiol. 66, 524-528.
8. Eggert, C., Temp, U., Dean, J.F.D. & Eriksson, K.-E.L. (1996) A fungal metabolite mediates degradation of non-phenolic lignin structures and synthetic lignin by laccase. FEBS Lett. 391, 144-148.
9. Li, K., Xu, F. & Eriksson, K.-E.L. (1999) Comparison of fungal laccases and redox mediators in oxidation of a nonphenolic lignin model compound. Appl. Environ. Microbiol. 65, 2654-2660.
10. Cantarella, G., Galli, C. & Gentili, P. (2003) Free radical vs. electron-transfer routes of oxidation of hydrocarbons by laccase/mediator systems. Catalytic or stoichiometric procedures. J. Mol. Catal. B: Enzym. 22, 135-144.
11. Cantarella, G., d'Acunzo, F. & Galli, C. (2003) Determination of laccase activity in mixed solvents. A comparison between two chromogens in a spectrophotometric assay. Biotechnol. Bioeng. 82, 395-398.
12. d'Acunzo, F., Baiocco, P. & Galli, C. (2003) A study of the oxidation of ethers with the enzyme laccase under mediation by two N-OH-type compounds. New J. Chem. 27, 329-332.
13. Baiocco, P., Barreca, A.M., Fabbrini, M., Galli, C. & Gentili, P. (2003) Promoting laccase activity towards non-phenolic substrates: a mechanistic investigation with some enzyme/mediator systems. Org. Biomol. Chem. 1, 191-197.
14. Fabbrini, M., Galli, C., Gentili, P. & Macchitella, D. (2001) An oxidation of alcohols by oxygen with the enzyme laccase and mediation by TEMPO. Tetrahedron Lett. 42, 7551-7553.
15. Fabbrini, M., Galli, C. & Gentili, P. (2002) Comparing the catalytic efficiency of some mediators of laccase. J. Mol. Cat. B: Enzym. 16, 231-240.
16. 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.
17. Wolfenden, B.S. & Willson, R.L. (1982) Radical cations as reference chromogens in kinetic studies of one-electron transfer reactions: pulse radiolysis studies of ABTS. J. Chem. Soc. Perkin Trans. 2, 805-812.
18. d'Acunzo, F., Galli, C. & Masci, B. (2002) Oxidation of phenols by laccase and laccase-mediator systems. Solubility and steric issues. Eur. J. Biochem. 269, 5330-5335.
19. + ions. Ionic isomer quantitation with neutralization-reionization mass spectrometry. J. Am. Chem. Soc. 113, 9499-9503.
20. Bumpus, J.A., Tien, M., Wright, D. & Aust., S.D. (1985) Oxidation of persistent environmental pollutants by a white rot fungus. Science 228, 1434-1436.
21. d'Acunzo, F., Baiocco, P., Fabbrini, M., Galli, C. & Gentili, P. (2002) The radical rate-determining step in the oxidation of benzyl alcohols by two N-OH-type mediators of laccase: the polar N-oxyl radical intermediate. New J. Chem. 26, 1791-1794.
22. 5-. J. Mol. Catal. B: Enzym. 22, 13-20.
23. Bourbonnais, R., Leech, D. & Paice, M.G. (1998) Electrochemical analysis of the interactions of laccase mediators with lignin model compounds. Biochim. Biophys. Acta 1379, 381-390.
24. 13C-labeled galvinoxyl-type tetraradical. J. Am. Chem. Soc. 111, 108-114.
25. Casula, R., Crisponi, G., Cristiani, F., Nurchi, V., Casu, M. & Lai, A. (1993) Characterization of the ionization and spectral properties of sulfonephthalein indicators. Correlation with substituent effects and structural features. Talanta 40, 1781-1788.
26. Perrin, D.D. (1965) Dissociation Constants of Organic Acids in Aqueous Solution. Butterworths, London.
27. Silverman, R.B. (2000) Reduction and oxidation. In The Organic Chemistry of Enzyme-Catalyzed Reactions, pp. 157-158. Academic Press, San Diego, CA.
28. Wachter, R.M. & Branchaud, B.P. (1996) Molecular modeling studies on oxidation of hexopyranoses by galactose oxidase. An active site topology apparently designed to catalyze radical reactions, either concerted or stepwise. J. Am. Chem. Soc. 118, 2782-2789.
29. Hoffman, M.Z. & Li, C. (1999) One-electron redox potentials of phenols in aqueous solution. J. Phys. Chem. B 103, 6653-6656.
30. Muramatsu, M. (1958) Studies on the interaction of surface films with solute in solutions. Bull. Chem. Soc. Jpn 31, 864-871.