Copper catechol-driven Fenton reactions and their potential role in wood degradation

International Biodeterioration and Biodegradation

Volumn 61, Issue 4, 2008, Pages 345-350

  Valenzuela, Roberto ^a   Contreras, David ^a   Oviedo, Claudia ^b   Freer, Juanita ^a   Rodríguez, Jaime ^a  

^a UNIVERSITY OF CONCEPCIÓN   (Chile)

^b UNIVERSIDAD DEL BÍO BÍO   (Chile)

Author keywords

Brown rot fungi; Catechol; Copper; Fenton reaction; Non enzymatic biodegradation; Veratryl alcohol

Indexed keywords

ALCOHOLS; BIODEGRADATION; DEPOLYMERIZATION; FREE RADICAL POLYMERIZATION; WOOD;

CATECHOLS; FENTON REACTIONS; NON ENZYMATIC BIODEGRADATION; OXIDATIVE DEPOLYMERIZATION;

REACTION KINETICS;

BIODEGRADATION; CELLULOSE; COPPER; EXPERIMENTAL DESIGN; FUNGAL DISEASE; FUNGUS; IRON; LIGNIN; PERFORMANCE ASSESSMENT; PH; PHENOL; REDOX POTENTIAL; WOOD;

ALCOHOLS; BIODEGRADATION; DEPOLYMERIZATION; REACTION KINETICS; WOOD;

FUNGI;

EID: 43649084951     PISSN: 09648305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibiod.2007.10.006     Document Type: Article

References (25)

1. 2+ reduction by phenol derivatives associated with Azure B degradation in Fenton-like reactions. Chemosphere 66 (2007) 947-954
2. Barros, B., Scarminio, I.S., Bruns, R.E., 2001. Como fazer experimentos. Pesquisa e desenvolvimento na ciência e na indústria. Editora da UNICAMP, Campinas.
3. 2+ ions: implications for their antioxidant properties. Biochemical Journal 330 (1998) 1173-1178
4. Contreras D., Freer J., and Rodriguez J. Veratryl alcohol degradation by a catechol-driven Fenton reaction as lignin oxidation by brown-rot fungi model. International Biodeterioration & Biodegradation 57 (2006) 63-68
5. Demmin T., Swerdloff M., and Rogic M. Copper(II)-induced oxidations of aromatics subtrates: catalytic conversion of catechols to o-benzoquinones. Copper phenoxides as intermediates in the oxidation of phenol and a single-step conversion of phenol, ammonia and oxygen into muconic acid mononotrile. Journal of the American Chemical Society 103 (1981) 5795-5804
6. Goldstein S., Meyerstein D., and Czapski G. The Fenton reagents. Free Radical Biology and Medicine 15 (1993) 435-445
7. Goodell B., Jellison J., Liu J., Daniel G., Paszczynski A., Fekete F., Krishnamurthy S., Jun L., and Xu G. Low molecular weight chelators and phenolic compounds isolated from wood decay fungi and their role in the fungal biodegradation of wood. Journal of Biotechnology 53 (1997) 133-162
8. Goodell B., Daniel G., Jellison J., and Qian Y.H. Iron-reducing capacity of low-molecular-weight compounds produced in wood by fungi. Holzforschung 60 (2006) 630-636
9. Henry W.P. Non-enzymatic iron, manganese and cooper chemistry of potential importance in wood decay. In: Goodell B., Nicholas D.D., and Schultz T.P. (Eds). Wood Deterioration and Preservation (2003), American Chemical Society, New York
10. Jellison J., Connolly J., Goodell B., Doyle B., Illman B., Fekete F., and Ostrofsky A. The role of cations in the biodegradation of wood by the brown rot fungi. International Biodeterioration & Biodegradation 39 (1997) 165-179
11. Jensen Jr. K.A., Houtman C.J., Ryan Z.C., and Hammel K.E. Pathways for extracellular Fenton chemistry in the brown rot basidiomycete Gloeophyllum trabeum. Applied and Environmental Microbiology 67 (2001) 2705-2711
12. Johnson G.R.A., and Nazhat N.B. Kinetics and mechanism of the reaction of the bis(1,10-phenanthroline) copper(I) ion with hydrogen peroxide in aqueous solution. Journal of the American Chemical Society 109 (1987) 1990-1994
13. Johnson G.R.A., Nazhat N.B., and Saadallanazhat R.A. Reaction of the Aquacopper(I) ion with hydrogen-peroxide-evidence for a Cu III (Cupryl) intermediate. Journal of the Chemical Society-Faraday Transactions I 84 (1988) 501-510
14. Kamau P., and Jordan R.B. Kinetic study of the oxidation of catechol by aqueous copper (II). Inorganic Chemistry 41 (2002) 3076-3083
15. 2 in aqueous solutions: implications for wood decay. Environmental Science & Technology 39 (2005) 175-180
16. Mentasti E., Pelizzeti E., and Saini G. Reactions between iron(III) and catechol (o-dihydroxybenzene). 2. Equilibria and kinetics of redox reaction in aqueous acid solution. Journal of the Chemical Society-Dalton Transactions 23 (1973) 2690-2614.
17. Mentasti E., Pelizzeti E., and Saini G. Interactions of Fe(III) with adrenaline, l-dopa and other catechol derivatives-equilibria and kinetics of complex-formation in acidic perchlorate media. Journal of Inorganic & Nuclear Chemistry 38 (1976) 785-788
18. Mentasti E., and Pelizzetti E. Reactions between iron(III) and catechol (o-dihydroxybenzene). 1. Equilibria and kinetics of complex-formation in aqueous acid solution. Journal of the Chemical Society-Dalton Transactions 23 (1973) 2605-2608
19. Miller M. Use of dinitrosalicylic acid reagent for determination of reducing sugar. Analytical Chemistry 31 (1959) 426-429
20. Paszczynski A., Crawford R., Funk D., and Goodell B. De novo synthesis of 4,5-dimethoxycatechol and 2,5-dimethoxyhydroquinone by the brown rot fungus Gloeophyllum trabeum. Applied & Environmental Microbiology 65 (1999) 674-679
21. Rodriguez J., Parra C., Contreras D., Freer J., and Baeza J. Dihydroxybenzenes: driven Fenton reactions. Water Science and Technology 44 (2001) 251-256
22. Schweigert N., Zehnder A.J.B., and Eggen R.I.L. Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Environmental Microbiology 3 (2001) 81-91
23. Shah V., Verma P., Stopka P., Gabriel J., Baldrian P., and Nerud F. Decolorization of dyes with copper(II)/organic acid/hydrogen peroxide systems. Applied Catalysis B-Environmental 46 (2003) 287-292
24. Stapley J.A., and BeMiller J.N. The Ruff degradation: a review of previously proposed mechanisms with evidence that the reaction proceeds by a Hofer-Moest-type reaction. Carbohydrate Research 342 (2007) 407-418
25. Yang J., Fu X., Jia Q., Shen J., Biggins J.B., Jiang J.Q., Zhao J.J., Schmidt J.J., Wang P.G., and Thorson J.S. Studies on the substrate specificity of Escherichia coli galactokinase. Organic Letters 5 (2003) 2223-2226