Skip to main content

Advertisement

Official Journal of the Japan Wood Research Society

Journal of Wood Science Cover Image

Degradation of a nonphenolic β-O-4 lignin model dimer by horseradish peroxidase with 1-hydroxybenzotriazole

Article metrics

  • 206 Accesses

  • 2 Citations

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

  1. 1.

    Bourbonnais R, Paice MG (1990) Oxidation of non-phenolic substrates. An expanded role for laccase in lignin biodegradation. FEBS Lett 267:99–102

  2. 2.

    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

  3. 3.

    Call HP, Mücke I (1997) History, overview and application of mediated lignolytic systems, especially laccase-mediator-systems (Lignozym process). J Biotechnol 53:163–202

  4. 4.

    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

  5. 5.

    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

  6. 6.

    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

  7. 7.

    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

  8. 8.

    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

  9. 9.

    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

  10. 10.

    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

  11. 11.

    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

  12. 12.

    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

  13. 13.

    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

Download references

Author information

Correspondence to Shingo Kawai.

Rights and permissions

Reprints and Permissions

About this article

Key words

  • Horseradish peroxidase
  • Laccase
  • Lignin model dimer
  • One-electron oxidation
  • Radical mediator