On the reactions of two fungal laceases differing in their redox potential with lignin model compounds: products and their rate of formation

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 18, 2009, Pages 8357-8365

  Maarit, Lahtinen ^a   Kristiina, Kruus ^b   Petri, Heinonen ^a   Jussi, Sipilä ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b VTT TECHNICAL RESEARCH CENTRE OF FINLAND   (Finland)

Author keywords

Electrospray ionization mass spectrometry; Guaiacyl; Lacease; Lignin; Liquid chromatography mass spectrometry; Melanocarpus albomyces; Model compound; Nuclear magnetic resonance spectroscopy; Oxidation; Product structure; Redox potential; Syringyl; Trametes hirsuta

Indexed keywords

MELANOCARPUS; MELANOCARPUS ALBOMYCES; TRAMETES; TRAMETES HIRSUTA;

LACCASE; LIGNIN;

ACETYLATION; ARTICLE; COMPARATIVE STUDY; ENZYMOLOGY; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION; SORDARIALES; TRAMETES;

ACETYLATION; KINETICS; LACCASE; LIGNIN; OXIDATION-REDUCTION; SORDARIALES; TRAMETES;

EID: 70349319657     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf901511k     Document Type: Article

References (31)

1. Baldrian, P. Fungal laceases-occurrence and properties. FEMS Microbiol. Rev. 2006, 30, 215-242.
2. Solomon, E. I.; Sundaram, U. M.; Machokin, T. E. Multicopper oxidases and oxygenases. Chem. Rev. 1996, 96, 2563-2605.
3. Thurston, C. F. The structure and function of fungal laceases. Microbiology 1994, 140, 19-26.
4. Ralph, J.; Brunow, G.; Boerjan, W. Lignins. In Encylopedia of Life Sciences; Wiley: Chichester, U.K., 2007; http://els.net/[doi:10.1002/ 9780470015902.a0020104].
5. Argyropoulos, D. S.; Menachem, S. B. Lignin. In Advances in Biochemical Engineering/Biotechnology; Eriksson, K.-E., Ed.; SpringerVerlag: Berlin, Germany, 1997; Vol. 57, pp 127-158.
6. Call, H. P.; Mücke, I. History, overview and applications of mediated lignolytic systems, especially laccase-mediator-systems (Lignozym®. J. Biotechnol. 1997, 53, 163-202.
7. Freudenberg, K.; Neish, A. C. In Constitution and Biosynthesis of Lignin; Freudenberg, K., Neish, A. C., Eds.; Springer-Verlag: Berlin, Germany, 1968.
8. Camarero, S.; Ibarra, D.; Martinez, M. J.; Martinez, A. T. Ligninderived compounds as efficient lacease mediators for decolorization of different types of recalcitrant dyes. Appl. Environ. Microbiol. 2005, 71, 1775-11748
9. Kirk, T. K.; Harkin, J. M.; Cowling, E. B. Degradation of the lignin model compound syringylglycol-β-guaiacyl ether by Polyporus versicolor and Stereum frustulatum. Biochim. Biophys. Acta 1968, 165, 145-163.
10. Wariishi, H.; Morohoshi, N.; Haraguchi, T. Degradation of lignin by the extracellular enzymes of Coriolus versicolor VII. Effective degradation of syringyl type β-aryl ether lignin model compound by lacease III. Mokuzai Gakkaishi 1987, 33, 892-898.
11. Kawai, S.; Higuchi, T.; Nabeta, K.; Okuyama, H. Degradation mechanisms of β-0-4 lignin substructure model compounds by lacease of Coriolus versicolor. In Biotechnology in Pulp and Paper Manufacture; Kirk, T.-K., Chang, H.-M., Eds.; Butterworth-Heinemann: New York, 1990; pp 359-365.
12. Kawai, S.; Umezawa, T.; Shimada, M.; Higuchi, T.; Koide, K.; Nishida, T.; Morohoshi, N.; Haraguchi, T. Ca-Cβ cleavage of phenolic β-1 lignin substructure model compound by lacease of Coriolus versicolor. Mokuzai Gakkaishi 1987, 33, 792-797.
13. Kawai, S.; Umezawa, T.; Higuchi, T. Degradation mechanisms of phenolic β-1 lignin substructure model compounds by lacease of Coriolus versicolor. Arch. Biochem. Biophys. 1988, 262, 99-110.
14. Crestini, C.; Jurasek, L.; Argyropoulos, D. On the mechanism of the laccase-mediator system in the oxidation of lignin. Chem.-Eur. J. 2003, 9, 5371-5378.
15. Crestini, C.; Argyropoulos, D. S. The early oxidative biodegradation steps of residual kraft lignin models with lacease. Bioorg. Med. Chem. 1998, 6, 2161-2169.
16. Adler, E.; Hernestam, S. Estimation of phenolic hydroxyl groups in lignin. I. Periodate oxidation of guaiacol compounds. Acta Chem. Scand. 1955, 9, 319-334.
17. Adler, E.; Lindgren, B. O.; Saedén, U. The β-guaiacyl ether of α-veratrylglycerol as a lignin model. Svensk Papperstidn. 1952, 55, 245-254.
18. Nakatsubo, F.; Sato, K.; Higuchi, T. Synthesis of guaiacylglycerolβ- guaiacyl ether. Holzforschung 1975, 29, 165-168.
19. Haikarainen, A.; Lahtinen, M.; Nousiainen, P.; Sipilä, J. Unpublished work.
20. Kiiskinen, L.-L.; Kruus, K.; Bailey, M.; Ylösmäki, E.; Siika-aho, M.; Saloheimo, M. Expression of Melanocarpus albomyces lacease in Trichoderma reesei and characterization of the purified enzyme. Microbiology 2004, 150, 3065-3074. (Pubitemid 39317807)
21. Rittstieg, K.; Suurnäkki, A.; Suortti, T.; Kruus, K.; Guebizt, G.; Buchert, J. Polymerization of guaiacol and phenolic β-0-4 substructure by Trametes hirsuta lacease in the presence of ABTS. Enzyme Microbiol. Technol 2002, 31, 403-410.
22. Niku-Paavola, M.-L.; Karhunen, E.; Saloia, P.; Raunio, V. Ligninolytic enzymes of the white-rot fungus Phlebia radiata. Biochem. J. 1988, 254, 877-884.
23. Johannes, C.; Majcherczyk, A. Lacease activity tests and lacease inhibitors. J. Biotechnol. 2000, 78, 193-199.
24. Shleev, S. V.; Morozova, O. V.; Nikitina, O. V.; Gorshina, E. S.; Rusinova, T. V.; Serezhenkov, V. A.; Burbaev, D. S.; Gazaryan, I. C.; Yaropolov, A. I. Comparison of physico-chemical charasteristics of four laceases from different basidiomycetes. Biochimie 2004, 86, 693-703.
25. Kawai, S.; Umezawa, T.; Higuchi, T. Oxidation of methoxylated benzyl alcohols by lacease of Coriolus versicolor in the presence of syringaldehyde. Wood Res. 1989, 76, 10-16.
26. Pew, J. C.; Connors, W. J. New structures from the dehydrogenation of model compounds related to lignin. Nature 1967, 215, 623-625.
27. Pew, J. C.; Connors, W. J. New structures from the enzymic dehydrogenation of lignin model p-hydroxy-a-carbinols. J. Org. Chem. 1969, 34, 580-584.
28. Vériot, G.; Dutasta, J.-P.; Matouzenko, G.; Collet, A. Synthesis of C3-cyclotriveratrylene ligands for iron(II) and iron(III) coordination. Tetrahedron 1995, 51, 389-400.
29. Potthast, A.; Rosenau, T.; Koch, H.; Fischer, K. The reaction of phenolic model compounds in the laccase-mediator system (LMS)investigations by matrix assisted laser desorption ionization time-offiight mass spectrometry (MALDI-TOF-MS). Holzforschung 1999, 53, 175-180.
30. Calcaterra, A.; Galli, C.; Gentili, P. Phenolic compounds as likely natural mediators of lacease: a mechanistic assesment. J. Mol. Catal. B: Enzymatic 2008, 51, 118-120.
31. Lahtinen, M.; Kruus, K.; Boer, H.; Kemell, M.; Andberg, M.; Viikari, L.; Sipilä, J. The effect of lignin model compound structure on the rate of oxidation catalyzed by two different fungal laceases. J. Mol. Catal. B: Enzymatic 2009, 57, 204-210.