Diastereomer selectivity in the degradation of a lignin model compound of the arylglycerol β-aryl ether type by white-rot fungi

Enzyme and Microbial Technology

Volumn 43, Issue 2, 2008, Pages 199-204

  Bohlin, Christina ^a   Lundquist, Knut ^b   Jönsson, Leif J ^a  

^a KARLSTAD UNIVERSITY   (Sweden)

^b CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

Diastereomers; Lignin biodegradation; Lignin model compound; White rot fungi

Indexed keywords

BIODEGRADATION; LIGNIN;

DIASTEREOMERS; LIGNIN BIODEGRADATION; LIGNIN MODEL COMPOUND; WHITE-ROT FUNGI;

FUNGI;

BRILLIANT BLUE; ETHER DERIVATIVE; GLYCEROL DERIVATIVE; LACCASE; LIGNIN; OXIDIZING AGENT; REAGENT;

ARTICLE; CONTROLLED STUDY; DECOLORIZATION; DEGRADATION; DIASTEREOISOMER; DIODE; ENZYME ACTIVITY; FUNGUS CULTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NONHUMAN; PHANEROCHAETE; PYCNOPORUS CINNABARINUS; SAMPLE; TRAMETES VERSICOLOR; ULTRAVIOLET RADIATION; WHITE ROT FUNGUS;

BIODEGRADATION; FUNGI; LIGNINS;

FUNGI; PHANEROCHAETE CHRYSOSPORIUM; PYCNOPORUS CINNABARINUS; TRAMETES VERSICOLOR;

EID: 44449174427     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2008.03.002     Document Type: Article

References (37)

1. Hong F., Jönsson L.J., Lundquist K., and Wei Y. Oxidation capacity of laccases and peroxidases as reflected in experiments with methoxy-substituted benzyl alcohols. Appl Biochem Biotechnol 129 (2006) 303-319
2. Bohlin C., Persson P., Gorton L., Lundquist K., and Jönsson L.J. Product profiles in enzymic and non-enzymic oxidations of the lignin model compound erythro-1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol. J Mol Catal B: Enzym 35 (2005) 100-107
3. Bohlin C., Andersson P.-O., Lundquist K., and Jönsson L.J. Differences in stereo-preference in the oxidative degradation of diastereomers of the lignin model compound 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol with enzymic and non-enzymic oxidants. J Mol Catal B: Enzym 45 (2007) 21-26
4. Brunow G., Lundquist K., and Gellerstedt G. Lignin. In: Sjöström E., and Alén R. (Eds). Analytical methods in wood chemistry, pulping, and papermaking (1999), Springer-Verlag, Berlin 77-124
5. Ralph J., Lundquist K., Brunow G., Lu F., Kim H., Schatz P.F., et al. Natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids. Phytochem Rev 3 (2004) 29-60
6. Akiyama T., Goto H., Nawawi D.S., Syafii W., Matsumoto Y., and Meshitsuka G. Erythro/threo ratio of β-O-4 structures as an important structural characteristic of lignin Part 4: variation in the erythro/threo ratio in softwood and hardwood lignins and its relation to syringyl/guaiacyl ratio. Holzforschung 59 (2005) 276-281
7. Jönsson L., Karlsson O., Lundquist K., and Nyman P.O. Stereospecificity in enzymic and non-enzymic oxidation of β-O-4 lignin model compounds. FEBS Lett 276 (1990) 45-48
8. Hammel K.E., Kapich A.N., Jensen Jr. K.A., and Ryan Z.C. Reactive oxygen species as agents of wood decay by fungi. Enzyme Microb Technol 30 (2002) 445-453
9. Reinhammar B. Laccase. In: Lontie R. (Ed). Copper proteins and copper enzymes (1984), CRC Press, Boca Raton, FL 1-35
10. Cassland P., and Jönsson L.J. Characterization of a gene encoding Trametes versicolor laccase A and improved heterologous expression in Saccharomyces cerevisiae by decreased cultivation temperature. Appl Microbiol Biotechnol 52 (1999) 393-400
11. Jönsson L., Karlsson O., Lundquist K., and Nyman P.O. Trametes versicolor ligninase: Isozyme sequence homology and substrate specificity. FEBS Lett 247 (1989) 143-146
12. Johansson T., and Nyman P.O. Isozymes of lignin peroxidase and manganese(II) peroxidase from the white-rot basidiomycete Trametes versicolor I. Isolation of enzyme forms and characterization of physical and catalytic properties. Arch Biochem Biophys 300 (1993) 49-56
13. Cameron M.D., Timofeevski S., and Aust S.D. Enzymology of Phanerochaete chrysosporium with respect to the degradation of recalcitrant compounds and xenobiotics. Appl Microbiol Biotechnol 54 (2000) 751-758
14. Srinivasan C., D'Souza T.M., Boominathan K., and Reddy C.A. Demonstration of laccase in the white rot basidiomycete Phanerochaete chrysosporium BKM-F1767. Appl Environ Microbiol 61 (1995) 4274-4277
15. Larrondo L.F., Salas L., Melo F., Vicuna R., and Cullen D. A novel extracellular multicopper oxidase from Phanerochaete chrysosporium with ferroxidase activity. Appl Environ Microbiol 69 (2003) 6257-6263
16. Kersten P., and Cullen D. Extracellular oxidative systems of the lignin-degrading Basidiomycete Phanerochaete chrysosporium. Fungal Genet Biol 44 (2007) 77-87
17. Bermek H., Li K., and Eriksson K.-E.L. Laccase-less mutants of the white-rot fungus Pycnoporus cinnabarinus cannot delignify kraft pulp. J Biotechnol 66 (1998) 117-124
18. Ibrahim W., and Lundquist K. Synthesis of erythro and threo forms of lignin models of the arylglycerol-β-guaiacyl ether type. Acta Chem Scand 48 (1994) 149-151
19. Li S., Lundquist K., and Paulsson M. Synthesis of guaiacylglycerol β-guaiacyl ether. Acta Chem Scand 49 (1995) 623-624
20. Adler E., Lindgren B.O., and Saedén U. The beta-guaiacyl ether of alpha-veratrylglycerol as a lignin model. Sven Papperstidn 55 (1952) 245-255
21. Adler E., and Gustafsson B. Darstellung der threo- und erythro-Formen des d,l-Guajacylglycerins und des d,l-Veratrylglycerins. Acta Chem Scand 17 (1963) 27-36
22. Tien M., and Kirk T.K. Lignin peroxidase of Phanerochaete chrysosporium. Methods Enzymol 161 (1988) 238-249
23. Jönsson L., Johansson T., Sjöström K., and Nyman P.O. Purification of ligninase isozymes from the white-rot fungus Trametes versicolor. Acta Chem Scand B 41 (1987) 766-769
24. Eggert C., Temp U., Dean J.F.D., and Eriksson K.-E.L. A fungal metabolite mediates degradation of non-phenolic lignin structures and synthetic lignin by laccase. FEBS Lett 391 (1996) 144-148
25. Swamy J., and Ramsay J.A. The evaluation of white rot fungi in the decoloration of textile dyes. Enzyme Microb Technol 24 (1999) 130-137
26. Machado K.M.G., Matheus D.R., and Bononi V.L.R. Ligninolytic enzymes production and Remazol Brilliant Blue R decolorization by tropical Brazilian basidiomycetes fungi. Braz J Microbiol 36 (2005) 246-252
27. Palmieri G., Cennamo G., and Sannia G. Remazol Brilliant Blue R decolourisation by the fungus Pleurotus ostreatus and its oxidative enzymatic system. Enzyme Microb Technol 36 (2005) 17-24
28. Soares G.M.B., de Amorim M.T.P., and Costa-Ferreira M. Use of laccase together with redox mediators to decolourize Remazol Brilliant Blue R. J Biotechnol 89 (2001) 123-129
29. Kirk T.K., Harkin J.M., and Cowling E.B. Oxidation of guaiacyl- and veratryl-glycerol-β-guaiacyl ether by Polyporus versicolor and Stereum frustulatum. Biochim Biophys Acta 165 (1968) 134-144
30. Kirk T.K., Mozuch M.D., and Tien M. Free hydroxyl radical is not involved in an important reaction of lignin degradation by Phanerochaete chrysosporium Burds. Biochem J 226 (1985) 455-460
31. 14C-labelled poplar wood lignin by selected white-rot fungi. Eur J Appl Microbiol Biotechnol 17 (1983) 235-242
32. Geng X., and Li K. Degradation of non-phenolic lignin by the white-rot fungus Pycnoporus cinnabarinus. Appl Microbiol Biotechnol 60 (2002) 342-346
33. Li K., Horanyi P.S., Collins R., Phillips R.S., and Eriksson K.-E.L. Investigation of the role of 3-hydroxyanthranilic acid in the degradation of lignin by white-rot fungus Pycnoporus cinnabarinus. Enzyme Microb Technol 28 (2001) 301-307
34. 2 and absence of stereospecificity in primary product formation during fungal metabolism of a lignin model compound. Biochim Biophys Acta 719 (1982) 284-291
35. Zitzelsberger W., Ziegler W., and Wallnöfer P.R. Stereospecificity of the degradation of veratrylglycerol-β-2,4-dichlorophenylether, a model compound for lignin bound xenobiotic residues by Phanerochaete chrysosporium, Corynebacterium equi and photosensitized riboflavin. Chemosphere 16 (1987) 1137-1142
36. Matsumoto Y., Hatori H., Minami K., and Ishizu A. Structural analysis of lignin by ozonation-structure of lignin in decayed wood. Proceedings of 6th International Symposium on Wood and Pulping Chemistry, vol. 1. Melbourne, Australia (1991) 293-295
37. Lundquist K., and Kirk T.K. De novo synthesis and decomposition of veratryl alcohol by a lignin-degrading basidiomycete. Phytochemistry 17 (1978) 1676