Applications of redox mediators in the treatment of organic pollutants by using oxidoreductive enzymes: A review

Critical Reviews in Environmental Science and Technology

Volumn 38, Issue 1, 2008, Pages 1-42

  Husain, Maroof ^a   Husain, Qayyum ^b  

^a UNIVERSITY OF COLORADO   (United States)

^b ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

Decontamination; Degradation; Laccases; Lignin peroxidases; Mn peroxidases; Organic pollutants; Peroxidases; Redox mediators; Remediation

Indexed keywords

LACCASES; LIGNIN PEROXIDASES; PEROXIDASES;

AROMATIC COMPOUNDS; DEGRADATION; ENZYMES; REDOX REACTIONS; WASTEWATER TREATMENT;

ORGANIC POLLUTANTS;

1 HYDROXYBENZOTRIAZOLE; 2,2 AZINO BIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); 2,2',6,6' TETRAMETHYLPIPERIDINE N OXYL; 2,6 ANTHRAQUINONEDISULFONIC ACID; 3 HYDROXYANTHRANILIC ACID; ACETANILIDE DERIVATIVE; ACETOSYRINGONE; ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; AZO REDUCTASE; BARBITURIC ACID DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; DICHLOROPHENOL RED; HORSERADISH PEROXIDASE; INDUSTRIAL EFFLUENT; LACCASE; LIGNIN PEROXIDASE; LYSOZYME; MANGANESE PEROXIDASE; MONOPHENOL MONOOXYGENASE; N HYDROXYACETANILIDE; OXIDOREDUCTASE; PHENOLSULFONPHTHALEIN; RADICAL; SULFONIC ACID DERIVATIVE; SYRINGALDEHYDE; TETRAMETHYLBENZIDINE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VERATRYL ALCOHOL; VIOLURIC ACID;

AROMATIC COMPOUNDS; DEGRADATION; ENZYMES; ORGANIC POLLUTANTS; REDOX REACTIONS; WASTEWATER TREATMENT;

DEGRADATION; EFFLUENT; ENZYME; MANGANESE; ORGANIC POLLUTANT; REMEDIATION; WASTEWATER; WATER TREATMENT;

ENZYME SUBSTRATE; NONHUMAN; ORGANIC POLLUTION; OXIDATION REDUCTION REACTION; REVIEW; SLUDGE DEWATERING; WASTE MANAGEMENT; WASTE WATER;

ARMORACIA RUSTICANA; BRASSICA RAPA SUBSP. RAPA; MOMORDICA CHARANTIA;

EID: 38549120258     PISSN: 10643389     EISSN: 15476537     Source Type: Journal    
DOI: 10.1080/10643380701501213     Document Type: Review

References (163)

1. Aitken, M.D., Massey, I.J., Chen, T., and Heck, P.E. Characterization of reaction products from enzyme catalyzed oxidation of phenolic pollutants. Water Res. 28, 1879-1889, 1994.
2. 14C-labeled 2-amino-4,6-dinitrotoluene by manganese-dependent peroxidase H5 from the white-rot fungus Phanerochaete chrysosporium. Appl. Microbiol. Biotechnol. 54, 659-664, 2000.
3. Akhtar, M., Blanchette, R.A., and Kirk, T.K. Fungal delignification and biochemical pulping of wood. Adv. Biochem. Eng./Biotechnol. 57, 159-195, 1997.
4. Akhtar, S, Khan, A.A., and Husain, Q. Potential of immobilized bitter gourd (Momordica charantia) peroxidases in the decolorization and removal of textile dyes from polluted wastewater and dyeing effluent. Chemosphere 60, 291-301, 2005a.
5. Akhtar, S., and Husain, Q. Potential applications of immobilized bitter gourd (Momordica charantia) peroxidase in the removal of phenols from polluted water. Chemosphere 65, 1228-1235, 2006.
6. Akhtar, S., Khan, A.A., and Husain, Q. Partially purified bitter gourd (Momordica charantia) peroxidase catalyzed decolorization of textile and other industrially important dyes. Bioresource Technol. 96, 1804-1811, 2005b.
7. Amitai, G.R., Adani, G., Sod-Moriah, I., Rabinovitz, A., Vincze, H., Leader, B., Chefetz, L., Leibovitz-Persky, D., Friesem, D., and Hadar, Y. Oxidative biodegradation of phosphorothiolates by laccase. FEBS Lett. 438, 195-200, 1998.
8. Ander, P., and Messner, K. Oxidation of 1-hydroxybenzotriazole by laccase and lignin peroxidase. Biotechnol. Technol. 12, 191-195, 1998.
9. Baciocchi, E., Bietti, M., Gerini, M.F., and Lanzalunga, O. The mediation of veratryl alcohol in oxidations promoted by lignin peroxidase: The lifetime of veratryl alcohol radical cation. Biochem. Biophys. Res. Commun. 293, 832-835, 2002.
10. Baiocco, P., Barecca, A.M., Fabbrini, M., Galli, C., and Gentili, P. Promoting laccase activity towards non-phenolic substrates: A mechanistic investigation with some laccase-mediator systems. Org. Biomol. Chem. 1, 191-197, 2003.
11. Barr, D.P., and Aust, S.D. Effect of superoxide and superoxide dismutase on lignin peroxidase-catalyzed veratryl alcohol oxidation. Arch. Biochem. Biophys. 311, 378-382, 1994.
12. Basheer, S., Kut, O.M., Prenosil, J.E., and Bourne, J.I. Kinetics of enzymatic degradation of cyanide. Biotechnol. Bioeng. 39, 629-634, 1992.
13. Bechtold, T., Burtscher, E., and Turcanu, A. Anthraquinones as mediators for the indirect cathodic reduction of dispersed organic dyestuffs. J. Electroanal. Chem. 465, 80-87, 1999.
14. Bhatt, N., Patel, K.C., Keharia, H., and Mdamvar, V. Decolorization of diazo-dye Reactive Blue 172 by Pseudomonas aeruginosa NBAR12. J. Basic Microbiol. 45, 407-418, 2005.
15. Bohmer, S., Messner, K., and Srebotnik, E. Oxidation of phenanthrene by a fungal laccase in the presence of 1-hydroxybenzotriazole and unsaturated lipids. Biochem. Biophys. Res. Commun. 244, 233-238, 1998.
16. Bourbonnais, R., and Paice, M.G. Enzymatic delignification of kraft pulp using laccase and a mediator. TAPPI J. 79, 199-204, 1996.
17. Bourbonnais, R., and Paice, M.G. Oxidation of non-phenolic substrates. An expanded role for laccase in lignin biodegradation. FEBS Lett. 267, 99-102, 1990.
18. Bourbonnais, R., Leech, D., and Paice, M.G. Electrochemical analysis of the interactions of laccase mediators with lignin model compounds. Biochim. Biophys. Acta 1379, 381-390 1998.
19. Bourbonnais, R., Paice, M.G., Freiermuth, B., Bodie, E., and Borneman, S. Reactivity of various mediators and laccases with Kraft pulp and lignin model compounds. Appl. Environ. Microbiol. 12, 4627-4632, 1997.
20. Bourbonnais, R., Paice, M.G., Reidm, I.D., Lanthier, P., and Yaguchi, M. Ligninolytic oxidation by laccase from Trametes versicolor and role of the mediator 2,2′-azino-bis-(3 ethyl benzothiozoline-6-sulfonate) in kraft deploymerization. Appl. Environ. Microb. 61, 11876-11880, 1995.
21. 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, 2604-2614, 2005.
22. Bratkovskaya, I., Ivanec, R., and Kulys, J. Mediator-assisted laccase-catalyzed oxidation of 4-hydroxybiphenyl. Biochemistry (Moscow) 71, 550-554, 2006.
23. Caldwell, S.R., and Raushell, F.M. Detoxification of organic phosphate pesticides using an immobilized phosphotriesterase from Pseudomonas diminuta. Biotechnol. Bioeng. 37, 103-109, 1991.
24. Call, H.P., and Muecke, I. History, overview and applications of mediated lignolytic systems, especially laccase-mediator-systems (Lignozym® process). J. Biotechnol. 53, 163-202, 1997.
25. Camarero, S., Ibarra, D., Martínez, M.J., and Martínez, A.J. Lignin-derived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes. Appl. Environ. Microbiol. 71, 1775-1784, 2005.
26. Campos, R., Kandelbauer, A., Robra, K.H., Cavaco-Paulo, A., and Guebitz, G. M. Indigo degradation with purified laccase from Trametes hirsuta andSclerotium rolfsii. J. Biotechnol. 89, 131-139, 2001.
27. Chance, B. The kinetics and stoichiometry of the transition from the primary to the secondary peroxidase-peroxide complexes. Arch. Biochem. Biophys. 41, 416-424, 1952.
28. Chapsal, J.M., Bourbigot, M.M., and Thomas, D. Oxidation of aromatic compounds by haemoglobin. Water Res. 20, 709-713, 1986.
29. Christian, V., Shrivastava, R., Shukla, D., Modi, H.A., and Vyas, B.R. Degradation of xenobiotic compounds by lignin-degrading white-rot fungi: Enzymology and mechanisms involved. Indian J. Exp. Biol. 43, 301-312, 2005.
30. Chung, N., and Aust, S.D. Veratryl alcohol-mediated indirect oxidation of pentachlorophenol by lignin peroxidase. Arch. Biochem. Biophys. 322, 143-148, 1995a.
31. Chung, N., Aust S.D. Veratryl alcohol-mediated indirect oxidation of phenol by lignin peroxidase. Arch. Biochem. Biophys. 316, 733-737, 1995b.
32. Claus, H., Faber, G., and Konig, H. Redox-mediated decolorization of synthetic dyes by fungal laccases. Appl. Microbiol. Biotechnol. 59, 672-678, 2002.
33. Collins, P.J., Dobson, A.D.W., and Field, J.A. Reduction of the 2,2-azinobis(3-ethylbenzthiazoline-6-sulfonate) cation radical by physiological organic acids in the absence and presence of manganese. Appl. Environ. Microbiol. 64, 2026-2031, 1998.
34. Cosio, I.G., Fishero, R.A., and Carroad, P.A. Bioconversion of shellfish waste: Waste pretreatment enzyme production, process design and economic analysis. J. Food Sci. 47, 901-905, 1982.
35. Crestini, C., Jurasek, L., and Argyropoulos, D.S. On the mechanism of the laccase-mediator system in the oxidation of lignin. Chemistry 9, 5371-5378, 2003.
36. Crestini, C.L., and Argyropoulos, D.S. The early oxidative biodegradation steps of residual kraft lignin models with laccase. Bioorg. Med. Chem. 6, 2161-2169, 1998.
37. d'Acunzo, F., and Galli, C. First evidence of catalytic mediation by phenolic compounds in the laccase-induced oxidation of lignin models. Eur. J. Biochem. 270, 3634-3640, 2003.
38. d'Acunzo, F., and Lanzalunga, O. First synthesis of a polysaccharide-supported lignin model compound and study of its oxidation promoted by lignin peroxidase. Biochem. Biophys. Res. Commun. 313, 17-21, 2004.
39. dos Santos Fde, J., Ximenes, V.F., da Fonseca, L.M., de Faria Oliveira, O.M., and Brunetti, I.L. Horseradish peroxidase-catalyzed oxidation of rifampicin: reaction rate enhancement by co-oxidation with anti-inflammatory drugs. Biol. Pharm. Bull. 28, 1822-1826, 2005.
40. Dunford, H.B., and Stillman, J.S. On the function and mechanism of action of peroxidases. Coord. Chem. Rev. 19, 187-251, 1976.
41. Dunford, H.B. Horseradish peroxidase: Structure and kinetic properties. In Peroxidases in Chemistry and Biology (Everse, J., Everse, K.E., and Grishman, M.B., Eds.), Vol. II, pp. 1-24, CRC Press, Boca Raton, FL, 1992.
42. Duran, N., and Esposito, E. Potential applications of oxidative enzymes and phenoloxidase-like compounds in wastewater and soil treatment: A review. Appl. Catal. B: Environ. 28, 83-99, 2000.
43. Duran, N., Rosa, M. A., D' Annibale, A., and Gianfreda, L. Applications of laccases and tyrosinases (phenoloxidases) immobilized on different supports: A review. Enzyme Microb. Technol. 31, 907-931, 2002.
44. Eggert, C., Temp, U., Dean, J.F., and Eriksson, K.-E.L. A fungal metabolic mediates degradation of non-phenolic lignin structures and synthetic lignin by laccase. FEBS Lett. 391, 144-148, 1996.
45. Enoki, M., Doi Y., and Iwata, T. Oxidative degradation of trans-1,4-polyisoprene cast films and single crystals by enzyme-mediator systems. Macromol. Biol. 3, 637-704, 2003b.
46. Enoki, M., Doi, Y., Iwata, T. Oxidative degradation of cis- and trans-1,4-polyisoprenes and vulcanized natural rubber with enzyme-mediator systems. Biomacromolecules 4, 314-320, 2003a.
47. Enoki, M., Kaita, S., Wakatsuki, Y., Doi Y., and Iwata, T. Oxidative degradation of cis- and trans-1,4-polybutadienes by horseradish peroxidase/1-hydroxybenzotriazole. Polym. Deg. Stabil. 84, 321-326, 2004.
48. Farrell, R.L., Murtagh, K.E., Tien, M., Mozuch, M.D., and Kirk, T.K. 1989. Physical and enzymatic properties of lignin peroxidase isoenzymes from Phanerochaete chrysosporium. Enzyme Microb. Technol. 11, 322-328, 1989.
49. Fedorova, T.V., Vilesov, A.S., Kurzeev, S.A., Stepanova, E.V., Landesman, E.O., and Koroleva, O.V. Development of a novel enzyme-redox-mediator system based on a fungal laccase and ruthenium complexes. Prikl. Biokhim. Mikrobiol. 42, 629-637, 2006.
50. Ferapontova, E.E., Castillo, J., and Gorton, L. Bioelectrocatalytic properties of lignin peroxidase from Phanerochaete chrysosporium in reactions with phenols, catechols and lignin-model compounds. Biochim. Biophys. Acta 1760, 1343-1354, 2006.
51. Fernandez-Sanchez, C., Tzanov, T., Gubitz, G.M., and Cavaco-Paulo, A. Voltammetric monitoring of laccase-catalyzed mediated reactions. Bioelectrochemistry 58, 149-156, 2002.
52. Forrow, N.J., and Walters, S.J. Transition metal half-sandwich complexes as redox mediators to glucose oxidase. Biosens. Bioelectron. 19, 763-770, 2004.
53. Fujita, K., Kondo, R., Sakai, K., Kashino, Y., Nishida, T., and Takahara, Y. Biobleaching of kraft pulp using white-rot fungus IZU-154. TAPPI J. 74, 123-127, 1991.
54. Georis, J., Lomascolo, A., Camarero, S., Dorgeo, V., Herpoel, I., Asther, M., Martinez, A.T., and Dauvrin, T. Pycnoporus cinnabarinus laccases: An interesting tool for food or non-food applications. Commun. Agric. Appl. Biol. Sci. 68, 263-266, 2003.
55. Gerini, M.F., and Lanzalunga, O. One electron oxidation of benzyltrialkylsilanes catalyzed by lignin peroxidase: Comparison with the oxidation induced by chemical oxidants. Biochem. Biophys. Res. Commun. 303, 567-571, 2003.
56. Gonzalez, A.K., Polvillo, O., Arias, M.E., Perestelo, F., Carnicero, A., Gonzalez-Vila, F.J., and Falcon, M.A. Early attack and subsequent changes produced in an industrial lignin by a fungal laccase and a laccase-mediator system: An analytical approach. Appl. Microbiol. Biotechnol. 73, 141-150, 2006.
57. Goodwin, D.C., Aust, S.D., and Grover, T.A. Determination of rate constants for rapid peroxidase reactions. Anal. Biochem. 231, 333-338, 1995a.
58. Goodwin, D.C., Aust, S.D., and Grover, T.A. Evidence for veratryl alcohol as a redox mediator in lignin peroxidasecatalyzed oxidation. Biochemistry 34, 5060-5065, 1995b.
59. Goodwin, D.C., Barr, D.P., Aust, S.D., and Grover, T.A. The role of oxalate in lignin peroxidase-catalyzed reduction: Protection from compound III accumulation. Arch. Biochem. Biophys. 315, 267-272, 1994.
60. Goodwin, D.C., Grover, T.A., and Aust, S.D. Redox mediation in the peroxidase-catalyzed oxidation of aminopyrine: Possible implications for drug-drug interactions. Chem. Res. Toxicol. 9, 476-483, 1996.
61. Goodwin, D.C., Grover, T.A., and Aust, S.D. Roles of efficient substrates in enhancement of peroxidase-catalyzed oxidations. Biochemistry 36, 139-147, 1997.
62. Gutierrez, A., Del Rio, J.C., Rencoret J., Ibarra, D., and Martinez, A.T. Main lipophilic extractives in different paper pulp types can be removed using the laccase-mediator system. Appl. Microbiol. Biotechnol. 72, 845-851, 2006.
63. Han MJ., Choi, H.T., and Song, H.G. Degradation of phenanthrene by Trametes versicolor and its laccase. J. Microbiol. 42, 94-98, 2004.
64. Hao, O.J., Kim, H., and Chiang, P.-C. Decolorization of wastewater. Crit. Rev. Environ. Sci. Technol. 30, 449-505, 2000.
65. Heinfling, A., Martinez, M.J., Martinez, A.T., Bergbauer, M., and Szewzyk, U. Transformation of industrial dyes by manganese peroxidases from Bjerkandera adusta and Pleurotus eryngii in a manganese- independent reaction. Appl. Environ. Microbiol. 64, 2788-2793, 1998a.
66. Heinfling, A., Ruiz-Duen, F. J., Martynez, M. J., Bergbauer, H., Szewzyk, U., and Martynez, A. T. A study on reducing substrates of manganese oxidizing peroxidases from Pleurotus eryngii andBjenkandera adusta. FEBS Lett. 428, 141-146, 1998b.
67. Hirai, H., Shibata, H., Kawai, S., and Nishida, T. Role of 1-hydroxybenzotriazole in oxidation by laccase from Trametes versicolor. Kinetic analysis of the laccase-1-hydroxybenzotriazole couple. FEMS Microbiol Lett. 265, 56-59, 2006.
68. Hu, X., Zhao, X., and Hwang, H.M. Comparative study of immobilized Trametes versicolor laccase on nanoparticles and kaolinite. Chemosphere 66, 1618-1626, 2007.
69. Huang, X., Wang, D., Liu, C., Hu, M., Qu, Y., Gao, P. The roles of veratryl alcohol and nonionic surfactant in the oxidation of phenolic compounds by lignin peroxidase. Biochem. Biophys. Res. Commun. 311, 491-494, 2003.
70. Husain, Q., and Jan, U. Detoxification of phenols and aromatic amines from polluted wastewater by using phenol oxidases. J. Sci. Ind. Res. 59, 286-293, 2000.
71. Husain, Q. Potential applications of the oxidoreductive enzymes in the decolorization and detoxification of textile and other synthetic dyes from polluted water: A review. Crit. Rev. Biotechnol. 26, 201-221, 2006.
72. Jeganathan, J, Bassi, A., and Nakhla, G. Pre-treatment of high oil and grease pet food industrial wastewaters using immobilized lipase hydrolyzation. J. Hazard. Mater. 137(1), 121-128, 2006.
73. Johannes, C., and Majcherczyk, A., and Huttermann, A. Oxidation of acenaphthene and acenaphthylene by laccase of Trametes versicolor in a laccase mediator system. J. Biotechnol. 61, 151-157, 1998.
74. Johannes, C., and Majcherczyk, A. Natural mediators in the oxidation of polycyclic hydrocarbons by laccase mediator system. Appl. Environ. Microbiol. 66, 524-528, 2000.
75. Johannes, C., Majcherczyk, A., and Huttermann, A. Degradation of anthracene by laccase of Trametes versicolor in the presence of different mediator compounds. Appl. Microbiol. Biotechnol. 46, 313-317, 1996.
76. Johnson, D.R., Park J., Kukor, J.J., and Abriola, L.M. Effect of carbon starvation on toluene degradation activity by toluene monooxygenase-expressing bacteria. Biodegradation 17(5), 437-445, 2006.
77. Kandelbauer, A., Erlacher, A., Cavaco-Paulo, A., and Guebitz, G.M. Laccase catalyzed decolorization of the synthetic dye Diamond Black PV 200 and some structurally related derivatives. Biocatal. Biotransform. 22, 331-339, 2004.
78. 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, 4907-4915, 2002.
79. Karam, J., and Nicell, J.A. Potential applications of enzymes in waste treatment. J. Chem. Technol. Biotechnol. 69, 141-147, 1997.
80. Karaseva, E.I., Gaponik, P.N., and Metelitsa, D.I. Characterization of peroxidase-catalyzed oxidation of chromogenic substrates by tetrazole and its 5-substituted derivatives. Prikl. Biokhim. Mikrobiol. 41, 148-157, 2005.
81. Karaseva, E.I., Losev, Iu.P., and Metelitsa, D.I. Peroxidase-catalyzed oxidation of 3,3′,5,5′-tetramethylbenzidine in the presence of 2,4-dinitrosoresorcinol and polydisulfide derivatives of resorcinol and 2,4-dinitrosoresorcinol. Bioorg. Khim. 28, 147-155, 2002.
82. Kawai, S., Umezawa, T., and Higuchi. T. Oxidation of methoxylated benzyl alcohols by laccase of Coriolus versicolor in the presence of syringaldehyde. Wood Res. 76, 10-16, 1989.
83. Keck, A., Klein, J., Kudlich, K., Stolz, A., Kuackmuss, H.J., and Mattes, R. Reduction of azo dyes by redox mediators originating in the naphthalenesulfonic acid degradation pathway of Sphingomonas sp. strain BN 6. Appl. Environ. Microbiol. 63, 3684-3690, 1997.
84. Kelder, P.P., de Mol, N.J., Fischer, M.J.E., and Janssen, L.H.M. Kinetic evaluation of the oxidation of phenothiazine derivatives by methemoglobin and horseradish peroxidase in the presence of hydrogen peroxide: Implications for the reaction mechanism. Biochim. Biophys. Acta 1205, 230-238, 1994.
85. Kersten, P.J., Kalyanaraman, B., Hammel, K., Reinhammar, B., and Kirk, T.K. Comparison of lignin peroxidase, horseradish peroxidase and laccase in the oxidation of methoxybenzenes. Biochem. J. 268, 475-480, 1990.
86. Keum, Y.S., and Li, Q.X. Fungal laccase-catalyzed degradation of hydroxy polychlorinated biphenyls. Chemosphere 56, 23-30, 2004.
87. Khan, A.A., and Husain, Q. Decolorization and removal of textile and non-textile dyes from polluted wastewater and dyeing effluent by using potato (Solanum tuberosum) soluble and immobilized polyphenol oxidase. Bioresource Technol. 98, 1012-1019, 2007b.
88. Khan, A.A., and Husain, Q. Potential of plant polyphenol oxidase in the decolorization and removal of textile and non-textile dyes. J. Environ. Sci. 19, 396-402, 2007a.
89. Knutson, K., and Ragauskas, A. Laccase-mediator biobleaching applied to a direct yellow dyed paper. Biotechnol. Prog. 20, 1893-1896, 2004.
90. Koduri., R.S., and Tien, M. Kinetic analysis of lignin peroxidase: Explanation for the mediation phenomenon by veratryl alcohol. Biochemistry 33, 4225-4230, 1994.
91. Koduri., R.S., and Tien, M. Oxidation of guaiacol by lignin peroxidase. Role of veratryl alcohol. J. Biol. Chem. 270, 22254-22258, 1995.
92. Kulshrestha, Y., and Husain, Q. Decolorization and degradation of acid dyes mediated by partially purified turnip (Brassica rapa) peroxidases. Toxicol. Environ. Chem. 89(2), 255-267, 2007.
93. Kulys, J., Bratkovskaja, I., and Vidziunaite, R. Laccase-catalysed iodide oxidation in presence of methyl syringate. Biotechnol. Bioeng. 92, 124-128, 2005.
94. Lei, Y., Mulchandani. A., and Chen, W. Improved degradation of organophosphorus nerve agents and p-nitrophenol by Pseudomonas putida JS444 with surface-expressed organophosphorus hydrolase. Biotechnol. Prog. 21(3), 678-681, 2005.
95. Li, K., Helm, R. F., and Erikssen, K.-E.L. Mechanistic studies of the oxidation of a non-phenolic lignin model compound by the laccase/1- hydroxybenzotriazole redox system. Biotechnol. Appl. Biochem. 27, 239-243, 1998.
96. Li, K., Xu, F., and Erickson, K-E.L. Comparision of fungal laccases and redox mediators in the oxidation of a non-phenolic lignin model compound. Appl. Environ. Microbiol. 65, 2654-2660, 1999.
97. Lundell, T. in Ligninolytic System of the White-Rot Fungus, Phlebia radiata: Lignin Model Compound Studies (Edinburg, G., and Howling, S., eds.), PhD thesis, University of Helsinki, Helsinki, 1993, pp. 313-319.
98. Majcherczyk, A., Johannes, C., and A. Huttermann A. Oxidation of polycyclic aromatic hydrocarbons (PAH) by laccase of Trametes versicolor. Enzyme Microb. Technol. 22, 335-341, 1998.
99. Marjasvaara, A., Torvinen, M., and Vainiotalo, P. Laccase-catalyzed mediated oxidation of benzyl alcohol: The role of TEMPO and formation of products including benzonitrile studied by nanoelectrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. J. Mass. Spectrom. 39, 1139-1146, 2004.
100. Maruyama, T., Komatsu, C., Michizoe, J., Ichinose, H., and Goto, M. Laccase-mediated oxidative degradation of the herbicide dymron. Biotechnol. Bioeng. 22, 426-430, 2006.
101. Mattinen, M.L., Kruus, K., Buchert, J., Nielsen, J.H., Andersen, H.J., and Steffensen, C.L. Laccase-catalyzed polymerization of tyrosine-containing peptides. FEBS J. 272, 3640-3650, 2005.
102. Matto, M., and Husain, Q. Decolorization of direct dyes by salt fractionated turnip proteins in the presence of hydrogen peroxide and redox mediators. Chemosphere 69(2), 338-345, 2007.
103. Mensee, A.H., Chen, W., and Mulchandani. A. Detoxification of the organophosphate nerve agent coumaphos using organophosphorus hydrolase immobilized on cellulose materials. J. Ind. Microbiol. Biotechnol. 32(11-12), 554-560, 2005.
104. Metelitza, D.I., Karasyova, E.I., Grintsevich, E.E., and Thorneley, R.N. Peroxidase-catalyzed co-oxidation of 3,3′,5,5′-tetramethylbenzidine in the presence of substituted phenols and their polydisulfides. J. Inorg. Biochem. 98, 1-9, 2004.
105. Muheim, A., Fiechter, A., Harvey, P. J., and Schoemaker H.E. On the mechanism of oxidation of non-phenolic lignin model compounds by the laccase-ABTS couple. Holzforschung 46, 121-126, 1992.
106. Nagai, M., Sato, T., Watanabe, H., Saito, K., Kawata, M., and Enei, H. Purification and characterization of an extracellular laccase from the edible mushroom Lentinula edodes, and decolorization of chemically different dyes. Appl. Microbiol. Biotechnol. 60, 327-335, 2002.
107. Nigam, P., Armour, G., Banat, I.M., Singh, D., and Marchant, R. Physical removal of textile dyes and solid state fermentation of dye adsorbed agricultural residue. Bioresource Technol. 72, 219-226, 2000.
108. Nyanhongo, G.S., Gomes, J., Guebitz, G.M., Zvauya, R., Read, J., and Steiner, W. Decolorization of textile dyes by laccases from a newly isolated strain of Trametes modesta. Water Res. 36, 1449-1456, 2002.
109. Odaci, D., Timur, S., Pazarlioglu, N., Kirgoz, U.A., and Telefuncu, A. Effects of mediators on the laccase biosensor response in paracetamol detection. Biotechnol. Appl. Biochem. 45, 23-28, 2006.
110. Ollikka, P., Alhoumaki, K., Leppanen, V. M., Glumoff, T., Raijola, T. and Suominen, Y. Decolorization of azo, triphenyl methane, heterocyclic and polymeric dyes by lignin peroxidase isoenzymes from Phenerochaete chrysosporium. Appl. Environ. Microbiol. 59, 4010-4016, 1993.
111. Olorunniji, F.J., Malomo, S.O., Adediran, S.A., and Odutuga, A.A. Promethazine oxidation by redox mediation in peroxidase reactions. Arch. Biochem. Biophys. 380, 251-256, 2000.
112. Paice, M.G., Jurasek, L., Ho, C., and Bourbonnais, R. Direct biological bleaching of hardwood kraft pulp with the fungus Coriolus versicolor. TAPPI J. 72, 217-221, 1989.
113. Palmieri, G., Cennamo, G., and Sannia, G. Remazol Brilliant Blue R decolorization by fugus Pleurotus ostreatus and its oxidative enzymatic system. Enzyme Microb. Technol. 36, 17-24, 2005.
114. Palonen, H., and Viikari, L. Role of oxidative enzymatic treatments on enzymatic hydrolysis of softwood. Biotechnol. Bioeng. 86, 550-557, 2004.
115. Peralta-Zamora, P., Pereira, C.M., Tiburtius, E.R., Moraes, S.G., Rosa, M.A., and Minussi, R.C. Decolorization of reactive dyes by immobilized laccase. Appl. Catal. 1295, 1-14, 2002.
116. Pilz, R., Hammer, E., Schauer, F., Kragl, U. Laccase-catalysed synthesis of coupling products of phenolic substrates in different reactors. Appl. Microbiol. Biotechnol. 60, 708-712, 2003.
117. Potthast, A., Rosenau, T., Chen, C. L., and Gratzl, J.S. A novel method for the conversion of benzyl alcohols to benzaldehydes by laccase-catalyzed oxidation. J. Mol. Catal. A 108, 5-9, 1996.
118. Rasmuessen, S.J.., Chung, N., Khindaria, A., Grover, T., and Aust, S.D. Reductions catalyzed by a quinone and peroxidases from Phanerochaete chrysosporium. Arch. Biochem. Biophys. 320, 243-249, 1995.
119. Reyes, P., Pickard, M. A., and Vazquez-Duhalt, R. Hydroxybenzotrizole increases the range of textile dyes decolorized by immobilized laccase. Biotechnol. Lett. 21, 875-880, 1999.
120. Robinson, T., McMullan, G., Marchant, R., and Nigam, P. Remediation of dyes in textile effluents: A critical review on current treatment technologies with a proposed alternative. Bioresource Technol. 77, 247-255, 2001.
121. Rodriguez-Couto, S., Sanroman, M., and Guebitz, G.M. Influence of redox mediators and metal ions on synthetic acid dye decolorization by crude laccase from T. hirsuta. Chemosphere 58, 417-422, 2005.
122. Russ, R., Rau, J., and Stolz, A. The function of cytoplasmic flavin reductases in the reduction of azo dyes by bacteria. Appl. Environ. Microbiol. 66, 1429-1434, 2000.
123. Salony, Mishra, S., and Bisaria, V.S. Production and characterization of laccase from Cyathus bulleri and its use in decolourization of recalcitrant textile dyes. Appl. Microbiol. Biotechnol. 71, 646-653, 2006.
124. Sariaslani, F.S., Beale, J.M., Jr., and Rosazza, P. Oxidation of rotenone by Polyporus anceps laccase. J. Nat. Prod. 47, 692-697, 1984.
125. Schneider, P., and Pedersen, A.H. Enhancement of laccase reactions. PCT world patent WO 95/01426. January 1995.
126. Sealey, J., and Ragauskas, A.J. Residual lignin studies of laccasede lignified kraft pulps. Enzyme Microb. Technol. 23, 422-426, 1998.
127. Shah, M.M., and Aust, S.D. Iodide as the mediator for the reductive reactions of peroxidases. J. Biol Chem. 268, 8503-8506, 1993.
128. Sheng, D., and Gold, M.H. Irreversible oxidation of ferricytochrome c by lignin peroxidase. Biochemistry 37, 2029-2036, 1998.
129. Shimazu, M., Mulchandani, A., and Chen, W. Simultaneous degradation of organophosphorus pesticides and p-nitrophenol by a genetically engineered Moraxella sp. with surface-expressed.Biotechnol. Bioeng. 76(4), 318-324, 2001.
130. Shleev, S.V., Khan, I.G., Gazaryan, I.G., Morozova, O.V., and Yaropolov, A.I. Novel laccase redox mediators: Spectral, electrochemical, and kinetic properties. Appl. Biochem. Biotechnol. 111, 167-184, 2003.
131. Shleev, S.V., Khan, I.G., Morozova, O.V., Mazhugo, Iu.M., Khalunina, A.S., and Iaropolov, A.I. Phenyl pyrazolones - Novel oxidoreductase redox-mediators for degradation of xenobiotics. Prikl. Biokhim Mikrobiol. 40, 165-172, 2004.
132. Shumakovich, G.P., Shleev, S.V., Morozova, O.V., Khohlov, P.S., Gazaryan, I.G., and Yaropolov, A.I. Electrochemistry and kinetics of fungal laccase mediators. Bioelectrochemistry 69, 16-24, 2006.
133. Sigoillot, C., Record, E., Belle, V., Robert, J.L., Levasseur, A., Punt, P.J., van den Hondel, C.A., Fournel, A., Sigoillot, J.C., and Asther, M. Natural and recombinant fungal laccases for paper pulp bleaching. Appl. Microbiol. Biotechnol. 64, 346-352, 2004.
134. Soares, G.M., Costa-Ferreira, M., and Pessoa de Amorim, M. T. Decolorization of an anthraquinone-type dye using a laccase formulation. Bioresource Technol. 9, 171-177, 2001a.
135. Soares, G.M., de Amorim, M.T., and Costa-Ferreira, M. Use of laccase together with redox mediators to decolorize Remazol Brilliant Blue R. J. Biotechnol. 89, 123-129, 2001b.
136. Song, H.K., and Palmore, G.T. Conductive polypyrrole via enzyme catalysis. J. Phys. Chem. B Condens. Matter Mater. Surf. Interfaces Biophys. 109, 19278-19287, 2005.
137. Srebotnik, E., and Hammel, K.E. Degradation of nonphenolic lignin by the laccase/1-hydroxybenzotriazole system. J. Biotechnol. 81, 179-188, 2000.
138. Sulistyaningdyah, W.T., Ogawa, J., Tanaka, H., Maeda, C., and Shimizu, S. Characterization of alkaliphilic laccase activity in the culture supernatant of Myrothecium verrucaria 24G-4 in comparison with bilirubin oxidase. FEMS Microbiol. Lett. 230, 209-214, 2004.
139. Sutherland, G.R., Khindaria, A., Chung, N., and Aust, S.D. The effect of manganese on the oxidation of chemicals by lignin peroxidase. Biochemistry 34, 12624-12629, 1995.
140. Tauber, M.M., Guebitz, G.M., and Rehorek, A. Degradation of azo dyes by laccase and ultrasound treatment. Appl. Environ. Microbiol. 71, 2600-2607, 2005.
141. ten Have, R., De Thouars, R.G., Swarts, H.J., and Field J.A. Veratryl alcohol-mediated oxidation of isoeugenyl acetate by lignin peroxidase. Eur. J. Biochem. 265, 1008-1014, 1999.
142. Teunissen, P.J., and Field, J.A. 2-Chloro-1,4-dimethoxybenzene as a novel catalytic cofactor for oxidation of anisyl alcohol by lignin peroxidase. Appl. Environ. Microbiol. 64, 830-835, 1998b.
143. Teunissen, P.J., and Field, J.A. 2-Chloro-1,4-dimethoxybenzene as a mediator of lignin peroxidase catalyzed oxidations. FEBS Lett. 439, 219-223, 1998a.
144. Thomas, L., Jungschaffer, G., and Sproessler, B. Improved sludge dewatering by enzymatic treatment. Water Sci. Technol. 28, 189-192, 1993.
145. Thomas, O.R.T., and White, G.F. Immobilization of the surfactant-degrading bacterium Pseudomonas C12B in polyacrylamide gel. III. Biodegradation specificity for raw surfactant and industrial wastes. Enzyme Microb. Technol. 13, 338-343, 1991.
146. Tien, M., and Ma, D. Oxidation of 4-methoxymandelic acid by lignin peroxidase. Mediation by veratryl alcohol. J. Biol. Chem. 272, 8912-8917, 1997.
147. Tominaga, J., Michizoe, J., Kamiya, N., Ichinose, H., Maruyama, T., and Goto, M. Factors affecting the oxidative activity of laccase towards biphenyl derivatives in homogeneous aqueous-organic systems. J. Biosci. Bioeng. 98, 14-19, 2004.
148. Torres, E., Bustos-Jaimes, I., and LeBorgne, S. Potential use of oxidative enzymes for the detoxification of organic pollutants. Appl. Catal. B Environ. 46, 1-15, 2003.
149. Trupkin, S., Levin, L., Forchiassin, F., and Viale, A. Optimization of a culture medium for ligninolytic enzyme production and synthetic dye decolorization using response surface methodology. J. Ind. Microbiol. Biotechnol. 30, 682-690, 2003.
150. Uetrecht, J.P., Ma, H.M., MacKnight, E., and McClelland, R. Oxidation of aminopyrine by hypochlorite to a reactive dication: Possible implications for aminopyrine-induced agranulocytosis. Chem. Res. Toxicol. 8, 226-233, 1995.
151. van der Zee, F.P., Lettinga, G. and Field, J.A. Azo dye decolourisation by anaerobic granular sludge. Chemosphere 44, 1169-1176, 2001.
152. van der Zee, F.P., Lettinga, G. and Field, J.A. The role of (auto)catalysis in the mechanism of an anaerobic azo reduction. Water Sci. Technol. 42, 301-308, 2000.
153. Vandertol-Vanier, H.A., Vazquez-Duhalt, R., Tinoco, R., and Pickard, M.A. Enhanced activity by poly(ethylene glycol) modification of Coriolopsis gallica laccase. J. Ind. Microbiol. Biotechnol. 29, 214-220, 2002.
154. Verma, P., and Madamwar, D. Decolorization of synthetic textile dyes by lignin peroxidase of Phanerochaete chrysosporium. Folia Microbiol. (Praha). 47, 283-286, 2002.
155. Wells, A., Teria, M., and Eve, T. Green oxidations with laccase-mediator systems. Biochem. Soc. Trans. 34, 304-308, 2006.
156. Won, K., Kim, Y.H., An, E.S., Lee, Y.S., and Song, B.K. Horseradish peroxidase-catalyzed polymerization of cardanol in the presence of redox mediators. Biomacromolecules 5, 1-4, 2004.
157. Wong, Y., and Yu, J. Laccase-catalyzed decolorization of synthetic dyes. Water Res. 33, 3512-3520, 1999.
158. Xu, F. Effects of redox potential and hydroxide inhibition on the pH activity profile of fungal laccases. J. Biol. Chem. 272, 924-928, 1997.
159. Xu, F., Juozas J., Kulys, J.J., Duke, K., Li, K., Krikstopaitis, K., Heinz-Josef, W., Deussen, H.-J.W., Abbate, E., Vilija Galinyte, V., and Schneider, P. Redox chemistry in laccase-catalyzed oxidation of N-hydroxy compounds. Appl. Environ. Microbiol. 66, 2052-2056, 2000.
160. Xu, F. Oxidation of phenols, anilines and benzinothiols by fungal laccases: Correlation between activity and redox potential as well as halide inhibition. Biochemistry 35, 7608-7614, 1996.
161. Xu, F. Recent progress in laccase study: Properties, enzymology, production, and applications. In M.C. Flickinger and S.W. Drew (eds.), The Encyclopedia of Bioprocessing Technology: Fermentation, Biocatalysis, and Bioseparation, pp. 1545-1554, John Wiley & Sons, New York, 1999.
162. Yeager, C.M., Arthur, K.M., Bottomley, P.J., and Arp, D.J. Trichloroethylene degradation by toluene-oxidizing bacteria grown on non-aromatic substrates. Biodegradation 15(1), 19-28, 2004.
163. Zille, A., Ramalho, P., Tzanov, T., Millward, R., Aires, V., Cardoso, M. H., Ramalho, M. T., Guebitz, G. M., and Cavaco-Paulo, A. Predicting dye biodegradation from redox potentials. Biotechnol. Prog. 20, 1588-1592, 2004.