- Note
- Published:
Degradation of a nonphenolic β-O-4 lignin model dimer by horseradish peroxidase with 1-hydroxybenzotriazole
Journal of Wood Science volume 52, pages 363–366 (2006)
Abstract
Nonphenolic β-O-4 lignin substructure model dimer, 1,3-dihydroxy-2-(2,6-dimethoxyphenoxy)-1-(4-ethoxy-3-methoxyphenyl)propane (I) was degraded by horseradish peroxidase (HRP) in the presence of hydrogen peroxide and 1-hydroxybenztriazole (HBT). 4-Ethoxy-3-methoxybenzoic acid (II), 1-(4-ethoxy-3-methoxyphenyl)-3-hydroxypropanone (III), 2,3-dihydroxy-1-(4-ethoxy-3-methoxyphenyl)-1-formyloxypropane (IV), 2,3-dihydroxy-1-(4-ethoxy-3-methoxyphenyl)propanone (V), 1-(4-ethoxy-3-methoxyphenyl)-1,2,3-trihydroxypropane (VI), 1-(4-ethoxy-3-methoxyphenyl)-1,2,3-trihydroxypropane-2,3-cyclic carbonate (VII), and 1-(4-ethoxy-3-methoxyphenyl)-1,2,3-trihydroxypropane-1,2-cyclic carbonate (VIII) were identified as degradation products by gas chromatography-mass spectrometry. These degradation products were qualitatively the same as those of substrate I in the laccase/HBT system, but the yield of the products was apparently different. The products catalyzed by the HRP/H2O2/HBT system contained large amounts of the aromatic ring cleavage products IV, VII, and VIII compared with those catalyzed by the laccase/HBT system, while the amount of Cα-Cβ cleavage product II is relatively low. These results suggest that the role of HBT is not in a simple one-electron transfer between the enzymes and substrates.
References
Bourbonnais R, Paice MG (1990) Oxidation of non-phenolic substrates. An expanded role for laccase in lignin biodegradation. FEBS Lett 267:99–102
Bourbonnais R, Paice MG, Freiermuth B, Bodie E, Borneman S (1997) Reactivities of various mediators and laccases with kraft pulp and lignin model compounds. Appl Environ Microbiol 63:4627–4632
Call HP, Mücke I (1997) History, overview and application of mediated lignolytic systems, especially laccase-mediator-systems (Lignozym process). J Biotechnol 53:163–202
Li K, Xu F, Erikssen KEL (1999) Comparison of fungal laccases and redox mediators of a non phenolic lignin model compound. Appl Environ Microbiol 65:2654–2660
Kawai S, Asukai M, Ohya N, Okita K, Ito T, Ohashi H (1999) Degradation of a nonphenolic β-O-4 substructure and of polymeric lignin model compounds by laccase of Coriolus versicolor in the presence of 1-hydroxybenzotriazole. FEMS Microbiol Lett 170:51–57
Kawai S, Nakagawa M, Ohashi H (1999) Aromatic ring cleavage of a nonphenolic β-O-4 lignin model dimer by laccase of Trametes versicolor in the presence of 1-hydroxybenzotriazole. FEBS Lett 446:355–358
Kawai S, Nakagawa M, Ohashi H (2002) Degradation mechanisms of a nonphenolic β-O-4 lignin model dimer by laccase of Trametes versicolor in the presence of 1-hydroxybenzotriazole. Enzyme Microb Technol 30:482–489
Kawai S, Iwatsuki M, Nakagawa M, Inagaki M, Hamabe A, Ohashi H (2004) An alternative b-ether cleavage pathway for a non-phenolic β-O-4 lignin model dimer catalyzed by a laccase-mediator system. Enzyme Microb Technol 35:154–160
Kawai S, Ohashi H, Hirai T, Okuyama H, Higuchi T (1993) Degradation of syringyl lignin model polymer by laccase of Coriolus versicolor. Mokuzai Gakkaishi 39:98–102
Leonowicz A, Grzywnowicz K (1981) Quantitative estimation of laccase forms in some white-rot fungi using syringaldazine as a substrate. Enzyme Microb Technol 3:55–58
Kawai S, Shoji S, Nabeta K, Okuyama H, Higuchi T (1990) Degradation of non-phenolic β-O-4 lignin substructure model compounds by lignin peroxidase of Coriolus versicolor. Mokuzai Gakkaishi 36:126–132
Kawai S, Umezawa T, Higuchi T (1985) Metabolism of a non-phenolic β-O-4 lignin substructure model compound by Coriolus versicolor. Agric Biol Chem 49:2325–2330
Shibata H, Hirai H, Nishida T, Ohnishi M (2003) The role of 1-hydroxybenzotriazol in laccase reaction system (in Japanese). Proceedings of the 48th Lignin Symposium, Fukui, pp 32-37
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kawai, S., Kobayashi, Y., Nakagawa, M. et al. Degradation of a nonphenolic β-O-4 lignin model dimer by horseradish peroxidase with 1-hydroxybenzotriazole. J Wood Sci 52, 363–366 (2006). https://doi.org/10.1007/s10086-005-0759-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10086-005-0759-y