Structure/Redox potential relationship of simple organic compounds as potential precursors of dyes for laccase-mediated transformation

Biotechnology Progress

Volumn 28, Issue 1, 2012, Pages 93-102

  Polak, Jolanta ^a   Jarosz Wilkolazka, Anna ^a  

^a MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

Coupling reactions; Dyes; Laccase; Phenolic compounds; Redox potential

Indexed keywords

AMINO GROUP; BENZENE DERIVATIVES; COLORED PRODUCTS; COUPLING REACTION; EXTRACELLULAR; FUNGAL LACCASES; LACCASES; METHOXY; METHOXY GROUP; METHOXYLATION; NORMAL HYDROGEN ELECTRODES; ORGANIC PRECURSOR; OXIDATION PEAK; PHENOLIC COMPOUNDS; REDOX POTENTIALS;

AMINATION; BENZENE; CATALYSIS; CYCLIC VOLTAMMETRY; DYES; HYDROGEN; OXIDATION; REDOX REACTIONS; SECONDARY BATTERIES; SUBSTRATES;

PHENOLS;

COLORING AGENT; LACCASE; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYMOLOGY; FUNGUS; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION;

CATALYSIS; COLORING AGENTS; FUNGI; KINETICS; LACCASE; ORGANIC CHEMICALS; OXIDATION-REDUCTION;

EID: 84856582073     PISSN: 87567938     EISSN: 15206033     Source Type: Journal    
DOI: 10.1002/btpr.713     Document Type: Article

References (51)

1. Dufosse L, Galaup P, Yaron A, Malis Arad S, Blanc P, Chidambara Murthy KN, Ravishankar GA. Microorganisms and microalgae as sources of pigments for food use: a scientific oddity or an industrial reality? Trends Food Sci Technol. 2005; 16: 384-406.
2. Duran N, Teixeira MFS, de Conti R, Esposito E. Ecological-friendly pigments from fungi. Crit Rev Food Sci Nutr. 2002; 42: 53-66.
3. Dufosse L. Microbial production of food grade pigments. Food Technol Biotechnol. 2006; 44: 313-321.
4. Rodriguez Couto S, Toca Herrera JL. Industrial and biotechnological applications of laccases: a review. Biotechnol Adv. 2006; 24: 500-513.
5. Riva S. Laccases: blue enzymes for green chemistry. Trends Biotechnol. 2006; 24: 219-226.
6. Kunamneni A, Camarero S, García-Burgos C, Plou FJ, Ballesteros A, Alcalde M. Engineering and applications of fungal laccases for organic synthesis. Microb Cell Fact. 2008; 7: 32-49.
7. Mikolasch A, Schauer F. Fungal laccase as tools for the synthesis of new hybrid molecules and biomaterials. Appl Microbiol Biotechnol. 2009; 82: 605-624.
8. Giardina P, Faraco V, Pezzella C, Piscitelli A, Vanhulle S, Sannia G. Laccases: a never-ending story. Cell Mol Life Sci. 2010; 67: 369-385.
9. Rodgers CJ, Blandford CF, Giddens SR, Skamnioti P, Armstrong FA, Gurr SJ. Designer laccases: a vogue for high-potential fungal enzymes. Trends Biotechnol. 2010; 28: 63-72.
10. Thurston CF. The structure and function of fungal laccases. Microbiology. 1994; 140: 19-26.
11. Luterek J, Gianfreda L, Wojtaś-Wasilewska M, Rogalski J, Jaszek M, Malarczyk E, Dawidowicz A, Ginalska G, Leonowicz A, Finks-Boots M. Screening of the wood rotting fungi for laccase production: induction by ferulic acid, partial purification, and immobilization of laccase from the high laccase-producing strain, Cerrena unicolor. Acta Biochim Pol. 1997; 46: 297-311.
12. McCaig BC, Meagher RB, Dean JFD. Gene structure and molecular analysis of the laccase-like multicopper oxidase (LMCO) gene family in Arabidopsis thaliana. Planta. 2005; 221: 619-636.
13. Martins LO, Soares CM, Pereira MM, Teixeira M, Costa T, Jones GH, Henriques AO. Molecular and biochemical characterization of a highly stable bacterial laccase that occurs as a structural component of the Bacillus subtilis endospore coat. J Biol Chem. 2002; 277: 18849-18859.
14. Dittmer NT, Suderman RJ, Jiang H, Zhu Y-C, Gorman MJ, Kramer KJ, Kanost MR. Characterization of cDNAs encoding putative laccase-like multicopper oxidases and developmental expression in the tobacco hornworm, Manduca sexta, and the malaria mosquito, Anopheles gambiae. Insect Biochem Mol Biol. 2004; 34: 29-41.
15. Xu F, Shin W, Brown SH, Waleithner JA, Sundaram UM, Solomon EI. A study of a series of recombinant fungal laccases and bilirubin oxidase that exhibit significant differences in redox potential, substrate specificity, and stability. Biochim Biophys Acta. 1996; 1292: 303-311.
16. Xu F. Effects of redox potential and hydroxide inhibition on the pH activity profile of fungal laccases. J Biol Chem. 1997; 272: 924-928.
17. Shleev S, Tkac J, Christenson A, Ruzgas T, Yaropolov AI, Whittaker JW, Gorton L. Direct electron transfer between copper-containing proteins and electrodes. Biosens Bioelectron. 2005; 20: 2517-2554.
18. Xu F. Oxidation of phenols, anilines, and benzenethiols by fungal laccases: correlation between activity and redox potential as well as halide inhibition. Biochemistry. 1996; 35: 7608-7614.
19. Abadulla E, Tzanov T, Costa S, Robra KH, Cavaco-Paulo A, Gubitz GM. Decolourisation and detoxification of textile dyes with laccase from Trametes hirsuta. Appl Environ Microbiol. 2000; 66: 3357-3362.
20. Camarero S, Ibarra D, Martinez AT, Romero J, Gutierrez A, del Rio JC. Paper pulp delignification using laccase and natural mediators. Enzyme Microb Technol. 2007; 40: 1264-1271.
21. Lante A, Crapisi A, Krastanov A, Spettoli P. Biodegradation of phenols by laccase immobilised in a membrane reactor. Process Biochem. 2000; 36: 51-58.
22. Hosny M, Rosazza JP. Novel oxidations of (+)-catechin by horseradish peroxidase and laccase. J Agric Food Chem. 2002; 50: 5539-5545.
23. Jarosz-Wilkołazka A, Ruzgas T, Gorton L. Amperometric detection of mono- and diphenols at Cerrena unicolor laccase-modified graphite electrode: correlation between sensitivity and substrate structure. Talanta. 2005; 66: 1219-1224.
24. Freire RS, Duran N, Kubota LT. Development of a laccase based flow injection electrochemical biosensor for the determination of phenolic compounds and its application for monitoring remediation of Kraft E1 paper mill effluent. Anal Chim Acta. 2002; 463: 229-238.
25. Jarosz-Wilkołazka A, Ruzgas T, Gorton L. Use of laccase-modified electrode for amperometric detection of plant flavonoids. Enzyme Microb Technol. 2004; 35: 238-241.
26. Martinez-Ortiz J, Flores R, Vazquez-Duhalt R. Molecular design of laccase cathode for direct electron transfer in a biofuel cell. Biosens Bioelectron. 2011; 26: 2626-2631.
27. Palmore GTR, Kim HH. Electro-enzymatic reduction of dioxygen to water in the cathode compartment of a biofuel cell. J Electroanal Chem. 1999; 464: 110-117.
28. Zille A, Górnacka B, Rehorek A, Cavaco-Paulo A. Degradation of azo dyes by Trametes villosa laccase over long periods of oxidative conditions. Appl Environ Microbiol. 2005; 71: 6711-6718.
29. Osiadacz J, Al-Adhami AJH, Bojraszewska D, Fischer P, Peczynska-Czoch W. On the use of Trametes versicolor laccase for the conversion of 4-methyl-3-hydroxyanthranilic acid to actinocin chromophore. J Biotechnol. 1999; 72: 141-149.
30. Sagui F, Chirivì C, Fontana G, Nicotra S, Passarella D, Riva S, Danieli B. Laccase-catalyzed coupling of catharanthine and vindoline: an efficient approach to the bisindole alkaloid anhydrovinblastine. Tetrahedron. 2009; 65: 312-317.
31. Anyanwutaku I, Petroski R, Rosazza J. Oxidative coupling of mithramycin and hydroquinone catalyzed by copper oxidases and benzoquinone. Implications for the mechanism of action of aureolic acid antibiotics. Bioorg Med Chem. 1994; 2: 543-551.
32. Setti L, Giuliani S, Spinozzi G, Pifferi PG. Laccase catalyzed-oxidative coupling of 3-methyl-2-benzothiazoline hydrazone and methoxyphenols. Enzyme Microb Technol. 1999; 25: 285-289.
33. Forte S, Polak J, Valensin D, Taddei M, Basosi R, Vanhulle S, Jarosz-Wilkołazka A, Pogni R. Synthesis and structural characterization of a novel phenoxazinone dye by use of a fungal laccase. J Mol Catal B. 2010; 63: 116-120.
34. Bruyneel F, Enaud E, Billottet L, Vanhulle S, Marchand-Bryaert J. Regioselective synthesis of 3-hydroxyorthanilic acid and its biotransformation into a novel phenoxazinone dye by use of laccase. Eur J Org Chem. 2008; 1: 72-79.
35. Enaud E, Trovaslet M, Bruyneel F, Billottet L, Karaaslan R, Sener ME, Coppens P, Casas A, Jaeger IJ, Hafner Ch, Onderwater RCA, Corbisier AM, Marchand-Brynaert J, Vanhulle S. A novel azoanthraquinone dye made through innovative enzymatic process. Dyes Pigm. 2010; 85: 99-108.
36. Mustafa R, Muniglia L, Rovel B, Girardin M. Phenolic colorants obtained by enzymatic synthesis using a fungal laccase in a hydro-organic biphasic system. Food Res Int. 2005; 38: 995-1000.
37. Jeon JR, Kim EJ, Murugesan K, Park HK, Kim YM, Kwon JH, Kim WG, Lee JY, Chang YS. Laccase-catalysed polymeric dye synthesis from plant-derived phenols for potential application in hair dyeing: enzymatic colourations driven by homo- or hetero-polymer synthesis. Microb Biotechnol. 2010; 3: 324-335.
38. Polak J, Jarosz-Wilkołazka A. Whole-cell fungal transformation of precursors into dyes. Microb Cell Fact. 2010; 9: 51-62.
39. Bourbonnais R, Leech D, Paice M. Electrochemical analysis of the interactions of laccase mediators with lignin model compounds. Biochim Biophys Acta. 1998; 1379: 381-390.
40. Fernández-Sánchez C, Tzanov T, Gübitz GM, Cavaco-Paulo A. Voltammetric monitoring of laccase-catalyzed mediated reactions. Biochemistry. 2002; 58: 149-156.
41. Yaropolov AI, Skorobogatko OV, Vartanov SS, Varfolomeyev SD. Laccase: properties, catalytic mechanism, and applicability. Appl Biochem Biotechnol. 1994; 49: 257-280.
42. Schleev S, Klis M, Wang Y, Rogalski J, Bilewicz R, Gorton L. Comparative spectroelectrochemical studies of lyophilized and nonlyophilized laccases from Cerrena unicolor Basidiomycete. Electroanalysis. 2007; 19: 1039-1047.
43. Zille A, Ramalho P, Tzanov T, Millward R, Aires V, Cardoso MH, Ramalho MT, Gübitz GM, Cavaco-Paulo A. Predicting dye biodegradation from redox potentials. Biotechnol Prog. 2004; 20: 1588-1592.
44. Zille A, Munteanu F-D, Gubitz GM, Cavaco-Paulo A. Laccase kinetics of degradation and coupling reactions. J Mol Catal B. 2005; 33: 23-28.
45. Johannes C, Majcherczyk A. Laccase activity and laccase inhibitors. J Biotechnol. 2000; 78: 193-199.
46. Potthast A, Rosenau T, Chen CL, Gratzl JS. A novel method for the conversion of benzyl alcohols to benzaldehydes by laccase-catalyzed oxidation. J Mol Catal A. 1996; 108: 5-9.
47. Bourbonnais R, Paice MG, Reid ID, Lanthier P, Yaguchi M. Lignin oxidation by laccase isozymes from Trametes versicolor and role of the mediator 2, 2′-azinobis(3-ethylbenzthiazoline-6-sulfonate) in kraft lignin depolymerization. Appl Environ Microbiol. 1995; 61: 1876-1880.
48. Campos AM, Lissi EA. Kinetics of the reaction between 2, 2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) derived radical cations and phenols. Int J Chem Kinetics. 1997; 29: 219-224.
49. Matsumura E, Yamamoto E, Numata A, Kawano T, Shin T, Murao S. Structures of the laccase-catalyzed oxidation products of hydroxybenzoic acids in the presence of ABTS [2, 2′-azinodi(3-ethylbenzothiazoline-6-sulfonic acid)]. Agric Biol Chem. 1986; 50: 1355-1357.
50. Henriquez C, Aliaga C, Lissi E. Kinetics profiles in the reaction of ABTS derived radicals with simple phenols and polyphenols. J Chil Chem. 2004; 49: 65-67.
51. Osman AM, Wong KKY, Hill SJ, Fernyhough A. Isolation and the characterization of the degradation products of the mediator ABTS-derived radicals formed upon reaction with polyphenols. Biochem Biophys Res Commun. 2006; 340: 597-603.