Methyl syringate: An efficient phenolic mediator for bacterial and fungal laccases

Bioresource Technology

Volumn 124, Issue , 2012, Pages 371-378

  Rosado, Tânia ^a   Bernardo, Pedro ^a   Koci, Kamila ^a   Coelho, Ana V ^a   Robalo, M Paula ^b,c   Martins, Lígia O ^a  

^a INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^b INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

^c INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Laccases; Lignin units; Natural mediators; Non phenolic; Phenolics; Radical coupling

Indexed keywords

LACCASES; NATURAL MEDIATORS; NON-PHENOLIC; PHENOLICS; RADICAL COUPLING;

CATALYTIC OXIDATION; LIGNIN; OXIDATION; REACTION INTERMEDIATES; REDOX REACTIONS;

PHENOLS;

BACTERIAL ENZYME; FUNGAL ENZYME; LACCASE; LIGNIN; PHENOL DERIVATIVE; SYRINGIC ACID METHYL ESTER; UNCLASSIFIED DRUG;

ENZYME; FUNGUS; OXIDATION; PH; PHENOLIC COMPOUND; REACTION KINETICS; REDOX POTENTIAL;

ARTICLE; BACILLUS SUBTILIS; BIOTRANSFORMATION; CONTROLLED STUDY; ENZYME MECHANISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION TRAP MASS SPECTROMETRY; MEDIATOR; NONHUMAN; OXIDATION KINETICS; OXIDATION REDUCTION POTENTIAL; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

BACTERIA; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FUNGI; GALLIC ACID; LACCASE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84867869530     PISSN: 09608524     EISSN: 18732976     Source Type: Journal    
DOI: 10.1016/j.biortech.2012.08.023     Document Type: Article

References (36)

1. Astolfi P., Brandi P., Galli C., Gentili P., Gerini M.F., Greci L., Lanzalunga O. New mediators for the enzyme laccase: mechanistic features and selectivity in the oxidation of non-phenolic substrates. New J. Chem. 2005, 29:1308-1317.
2. Aracri E., Fillat A., Colom J.F., Gutiérrez A., Del Rio J.C., Martínez A.T., Vidal T. Enzymatic grafting of simple phenols on flax and sisal pulp fibers using laccases. Bioresour. Technol. 2010, 101:8211-8216.
3. Bertrand T., Jolivalt C., Briozzo P., Caminade E., Joly N., Madzak C., Mougin C. Crystal structure of a four-copper laccase complexed with an arylamide: insights into substrate recognition and correlation with kinetics. Biochemistry 2002, 41:7325-7333.
4. Bortolomeazzi R., Sebastianutto N., Toniolo R., Pizzariello A. Comparative evaluation of the antioxidante capacity of smoke flavouring phenols by crocin bleaching inhibition, DPPH radical scavenging and oxidation potential. Food Chem. 2007, 100:1481-1489.
5. Bourbonnais R., Paice M.G. Oxidation of non-phenolic substrates. An expanded role for laccase in lignin biodegradation. FEBS Lett. 1990, 267:99-102.
6. d'Acunzo F., Galli C. First evidence of catalytic mediation by phenolic compounds in the laccase-induced oxidation of lignin models. Eur. J. Biochem. 2003, 270:3634-3640.
7. Calcaterra A., Galli C., Gentili P. Phenolic compounds as likely natural mediators of laccase: a mechanistic assessment. J. Mol. Cat. B 2008, 51:118-120.
8. Camarero S., Ibarra D., Martinez A.T., Romero J., Gutiérrez A., Del Rio J.C. Paper pulp delignification using laccase and natural mediators. Enzyme Microb. Technol. 2007, 40:1264-1271.
9. Camarero S., Ibarra D., Martínez M.J., Martínez A.T. Lignin-derived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes. Appl. Environ. Microbiol. 2005, 71:1775-1784.
10. Canas A.I., Camarero S. Laccases and their natural mediators: Biotechnological tools for sustainable eco-friendly processes. Biotechnol. Adv. 2010, 28:694-705.
11. Couto S.R., Herrera J.L.T. Industrial and biotechnological applications of laccases: a review. Biotechnol. Adv. 2006, 24:500-513.
12. Díaz-González M., Vidal T., Tzanov T. Electrochemical study of phenolic compounds as enhancers in laccase-catalyzed oxidative reactions. Electroanalysis 2009, 21:2249-2257.
13. Díaz-González M., Vidal T., Tzanov T. Phenolic compounds as enhancers in enzymatic and electrochemical oxidation of veratryl alcohol and lignins. Appl. Microbiol. Biotechnol. 2011, 89:1693-1700.
14. Deck J., Bollag J.-M. Dehalogenation of chlorinated phenols during oxidative coupling. Environ. Sci. Technol. 1994, 28:484-490.
15. Deck J., Haider K., Bollag J.-M. Release of substituents from phenolic compounds during oxidative coupling reactions. Chemosphere 2003, 52:549-556.
16. Enguita F.J., Martins L.O., Henriques A.O., Carrondo M.A. Crystal structure of a bacterial endospore coat component: a laccase with enhanced thermostability properties. J. Biol. Chem. 2003, 278:19416-19425.
17. Faure D., Bouillant M.L., Jacoud C., Bally R. Phenolic derivatives related to lignin metabolism as substrates for Azospirillum laccase activity. Phytochemistry 1996, 42:357-359.
18. Fillat A., Colom J.F., Vidal T. A new approach to the biobleaching of flax pulp with laccase using natural mediators. Bioresour. Technol. 2010, 101:4104-4110.
19. Kajiyama T., Ohkatsu Y. Effect of para-substituents of phenolic antioxidants. Polym. Degrad. Stab. 2001, 71:445-452.
20. Kallio J.P., Auer S., Jänis J., Andberg M., Kruus K., Rouvinen J., Koivula A., Hakulinen N. Structure-function studies of a Melanocarpus albomyces laccase suggest a pathway for oxidation of phenolic compounds. J. Mol. Biol. 2009, 392:895-909.
21. Kawai S., Umezawa T., Higushi T. Oxidation of methoxylated benzyl alcohols by laccase of Coriolus versicolor in the presence of syringaldehyde. Wood Res. 1989, 76:10-16.
22. González Arzola K., Arévalo M.C., Falcón M.A. Catalytic efficiency of natural and synthetic compounds used as laccase-mediators in oxidizing veratryl alcohol and a kraft lignin, estimated by electrochemical analysis. Electrochim. Acta 2009, 54:2621-2629.
23. Gutierrez A., Rencoret J., Ibarra D., Molina S., Camarero S., Romero J., Del Rio J.C., Martinez A.T. Removal of lipophilic extractives from paper pulp by laccase and lignin-derived phenols as natural mediators. Environ. Sci. Technol. 2007, 41:4124-4129.
24. Johannes C., Majcherczyk A. Natural mediators in the oxidation of polycyclic aromatic hydrocarbons by laccase mediator systems. Appl. Environ. Microbiol. 2000, 66:524-528.
25. Lahtinen M., Kruus K., Heinonen P., Sipilä J. On the reactions of two fungal laccases differing in their redox potential with lignin model compounds: products and their rate of formation. J. Agric. Food Chem. 2009, 57:8357-8365.
26. Madzak C., Mimmi M.C., Caminade E., Brault A., Baumberger S., Briozzo P., Mougin C., Jolivalt C. Shifting the optimal pH of activity for a laccase from the fungus Trametes versicolor by structure-based mutagenesis. Prot. Eng. Des. Sel. 2006, 19:77-84.
27. Martins L.O., Soares C.M., Pereira M.M., Teixeira M., Costa T., Jones G.H., Henriques A.O. 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.
28. Mikolasch A., Schauer F. Fungal laccase as tools for the synthesis of new hybrid molecules and biomaterials. Adv. Microbiol. Biotechnol. 2009, 82:605-624.
29. Martínez A.T., Ruiz-Duenas F.J., Martínez M.J., del Rio J.C., Gutíerrez A. Enzymatic delignification of plant cell wall: from nature to mill. Curr. Opin. Biotechnol. 2009, 20:348-357.
30. Nousiainen P., Maijala P., Hatakka A., Martínez A.T., Sipilä J. Syringyl-type simple plant phenolics as mediating oxidants in laccase catalyzed degradation of lignocellulosic materials: model compound studies. Holzforschung 2009, 63:699-704.
31. Riva S. Laccases: blue enzymes for green chemistry. Trends Biotechnol. 2006, 24:219-226.
32. Stewart D. Lignin as a base material for materials applications: chemistry, application and economics. Ind. Crop. Prod. 2010, 27:202-207.
33. Pereira L., Coelho A.V., Viegas C.A., Santos M.M., Robalo M.P., Martins L.O. Enzymatic biotransformation of the azo dye Sudan Orange G with bacterial CotA-laccase. J. Biotechnol. 2009, 139:68-77.
34. Piontek K., Antorini M., Choinowski T. Crystal structure of a laccase from the fungus Trametes versicolor at 1.90-A resolution containing a full complement of coppers. J. Biol. Chem. 2002, 277:37663-37669.
35. Wells A., Teria M., Eve T. Green oxidations with laccase-mediator systems. Biochem. Soc. Trans. 2006, 34:304-308.
36. Xu H., Lai Y.-Z., Slomczynski D., Nakas J.P., Tanenbaum S.W. Mediator-assisted selective oxidation of lignin model compounds by laccase from Botrytis cinerea. Biotechnol. Lett. 1997, 19:957-960.