Efficacy of mediators for enhancing the laccase-catalyzed oxidation of aqueous phenol

Enzyme and Microbial Technology

Volumn 41, Issue 3, 2007, Pages 353-361

  Kurniawati, Selvia ^a   Nicell, James A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

1 Hydroxybenzotriazole; ABTS; Enzyme stability; Exponential decay; Inactivation; Laccase; Mediator; Oxidation; Phenol; TEMPO; Transformation; Violuric acid

Indexed keywords

ENZYME STABILITY; EXPONENTIAL DECAY; LACCASE; VIOLURIC ACIDS;

CATALYSIS; ENZYMES; OXIDATION; PH EFFECTS; REDOX REACTIONS;

PHENOLS;

1 HYDROXYBENZOTRIAZOLE; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONATE); BENZOTRIAZOLE DERIVATIVE; LACCASE; PHENOL; PIPERIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; URIC ACID; VIOLURIC ACID;

ARTICLE; CATALYSIS; ENZYME INACTIVATION; ENZYME STABILITY; INCUBATION TIME; OXIDATION REDUCTION REACTION; PH;

TRAMETES VERSICOLOR;

EID: 34248579395     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2007.03.003     Document Type: Article

References (39)

1. Kersten P.J., Kalyanaraman B., Hammel K.E., Reinhammar B., and Kirk T.K. Comparison of lignin peroxidase, horseradish peroxidase, and laccase in the oxidation of methoxybenzenes. Biochem. J. 268 2 (1990) 475-480
2. Bourbonnais R., and Paice M.G. Oxidation of nonphenolic substrates-an expanded role for laccase in lignin biodegradation. FEBS Lett. 267 1 (1990) 99-102
3. Majcherczyk A., Johannes C., and Huttermann A. Oxidation of polycyclic aromatic hydrocarbons (PAH) by laccase of Trametes versicolor. Enzyme Microb. Technol. 22 5 (1998) 335-341
4. Fabbrini M., Galli C., and Gentili P. Comparing the catalytic efficiency of some mediators of laccase. J. Mol. Catal. B: Enzym. 16 5-6 (2002) 231-240
5. Banci L., Ciofi-Baffoni S., and Tien M. Lignin and Mn peroxidase-catalyzed oxidation of phenolic lignin oligomers. Biochemistry 38 10 (1999) 3205-3210
6. Kang K.H., Dec J., Park H., and Bollag J.M. Transformation of the fungicide cyprodinil by a laccase of Trametes villosa in the presence of phenolic mediators and humic acid. Water Res. 36 19 (2002) 4907-4915
7. Tsutsumi Y., Haneda T., and Nishida T. Removal of estrogenic activities of bisphenol A and nonylphenol by oxidative enzymes from lignin-degrading basidiomycetes. Chemosphere 42 3 (2001) 271-276
8. Kim Y.J., and Nicell J.A. Impact of reaction conditions on the laccase-catalyzed conversion of bisphenol A. Bioresour. Technol. 97 12 (2006) 1431-1442
9. Soares G.M.B., de Amorim M.T.P., and Costa-Ferreira M. Use of laccase together with redox mediators to decolourize Remazol Brilliant Blue R. J. Biotechnol. 89 2-3 (2001) 123-129
10. Li K.C., Xu F., and Eriksson K.E.L. Comparison of fungal laccases and redox mediators in oxidation of a nonphenolic lignin model compound. Appl. Environ. Microbiol. 65 6 (1999) 2654-2660
11. Fabbrini M., Galli C., Gentili P., and Macchitella D. An oxidation of alcohols by oxygen with the enzyme laccase and mediation by TEMPO. Tetrahedron Lett. 42 (2001) 7551-7553
12. Kim Y.J., and Nicell J.A. Laccase-catalyzed oxidation of bisphenol A with the aid of additives. Process Biochem. 41 5 (2006) 1029-1037
13. Call H.P., and Mucke I. History, overview and applications of mediated lignolytic systems, especially laccase-mediator systems (Lignozym™-process). J. Biotechnol. 53 2,3 (1997) 163-202
14. Nakamura T. Purification and physico-chemical properties of laccase. Biochim. Biophys. Acta 30 (1958) 44-52
15. Reinhammar B.R.M. Oxidation-reduction potentials of the electron acceptors in laccases and stellacyanin. Biochim. Biophys. Acta 275 2 (1972) 245-259
16. Yaropolov A.I., Skorobogatko O.V., Vartanov S.S., and Varfolomeyev S.D. Laccase-properties, catalytic mechanism, and applicability. Appl. Biochem. Biotechnol. 49 3 (1994) 257-280
17. Xu F. Oxidation of phenols, anilines, and benzenethiols by fungal laccases: correlation between activity and redox potentials as well as halide inhibition. Biochemistry 35 23 (1996) 7608-7614
18. Wolfenden B.S., and Willson R.L. Radical-cations as reference chromogens in kinetic-studies of one-electron transfer-reactions-pulse-radiolysis studies of 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulphonate). J. Chem. Soc.-Perkin Trans. 2 7 (1982) 805-812
19. Bourbonnais R., Paice M.G., Freiermuth B., Bodie E., and Borneman S. Reactivities of various mediators and laccases with kraft pulp and lignin model compounds. Appl Environ Microbiol 63 12 (1997) 4627-4632
20. Kurniawati S, Nicell JA. Characterization of Trametes versicolor laccase for the transformation of aqueous phenol (under review).
21. Kulys J., Vidziunaite R., and Schneider P. Laccase-catalyzed oxidation of naphthol in the presence of soluble polymers. Enzyme Microb Technol 32 3-4 (2003) 455-463
22. Buchanan I.D., and Nicell J.A. Model development for horseradish peroxidase catalyzed removal of aqueous phenol. Biotechnol Bioeng. 54 3 (1997) 251-261
23. Mita N., Tawaki S., Uyama H., and Kobayashi S. Laccase-catalyzed oxidative polymerization of phenols. Macromol. Biosci. 3 5 (2003) 253-257
24. Fabbrini M., Galli C., and Gentili P. Radical or electron-transfer mechanism of oxidation with some laccase/mediator systems. J. Mol. Catal. B: Enzym. 18 1-3 (2002) 169-171
25. d'Acunzo F., Baiocco P., Fabbrini M., Galli C., and Gentili P. 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 12 (2002) 1791-1794
26. d'Acunzo F., Baiocco P., Fabbrini M., Galli C., and Gentili P. A mechanistic survey of the oxidation of alcohols and ethers with the enzyme laccase and its mediation by TEMPO. Eur. J. Org. Chem. 24 (2002) 4195-4201
27. Xu F., Kulys J.J., Duke K., Li K.C., Krikstopaitis K., Deussen H.J.W., et al. Redox chemistry in laccase-catalyzed oxidation of N-hydroxy compounds. Appl. Environ. Microbiol. 66 5 (2000) 2052-2056
28. Cantarella G., Galli C., and Gentili P. Free radical versus electron-transfer routes of oxidation of hydrocarbons by laccase/mediator systems catalytic or stoichiometric procedures. J. Mol. Catal. B: Enzym. 22 3-4 (2003) 135-144
29. Bourbonnais R., Leech D., and Paice M.G. Electrochemical analysis of the interactions of laccase mediators with lignin model compounds. Biochim. Biophys. Acta 1379 3 (1998) 381-390
30. Xu F., Deussen H.J.W., Lopez B., Lam L., and Li K.C. Enzymatic and electrochemical oxidation of N-hydroxy compounds-redox potential, electron-transfer kinetics, and radical stability. Eur. J. Biochem. 268 15 (2001) 4169-4176
31. Xu F. Effects of redox potential and hydroxide inhibition on the pH activity profile of fungal laccases. J. Biol. Chem. 272 2 (1997) 924-928
32. Xu F. Dioxygen reactivity of laccase-dependence of laccase source, pH, and anion inhibition. Appl. Biochem. Biotechnol. 95 2 (2001) 125-133
33. Branchi B., Galli C., and Gentili P. Kinetics of oxidation of benzyl alcohols by the dication and radical cation of ABTS. Comparison with laccase-ABTS oxidations: an apparent paradox. Org. Biomol. Chem. 3 14 (2005) 2604-2614
34. Majcherczyk A., Johannes C., and Huttermann A. Oxidation of aromatic alcohols by laccase from Trametes versicolor mediated by the 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) cation radical and dication. Appl Microbiol Biotechnol 51 2 (1999) 267-276
35. Farneth W.E., Diner B.A., Gierke T.D., and D'Amore M.B. Current densities from electrocatalytic oxygen reduction in laccase/ABTS solutions. J Electroanal Chem 581 2 (2005) 190-196
36. Cecchetto A., Fontana F., Minisci F., and Recupero F. Efficient Mn-Cu and Mn-Co-TEMPO-catalysed oxidation of alcohols into aldehydes and ketones by oxygen under mild conditions. Tetrahedron Lett. 42 (2001) 6651-6653
37. Potthast A., Rosenau T., and Fischer K. Oxidation of benzyl alcohols by the laccase-mediator system (LMS)-a comprehensive kinetic description. Holzforschung 55 1 (2001) 47-56
38. Johannes C., and Majcherczyk A. Natural mediators in the oxidation of polycyclic aromatic hydrocarbons by laccase mediator systems. Appl Environ Microbiol 66 2 (2000) 524-528
39. Srebotnik E., and Hammel K.E. Degradation of nonphenolic lignin by the laccase/1-hydroxybenzotriazole system. J Biotechnol 81 2-3 (2000) 179-188