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Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases

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Abstract

The aim of this work has been to study the substrate specificity of two aromatic peroxygenases concerning polyaromatic compounds of different size and structure as well as to identify the key metabolites of their oxidation. Thus, we report here on new pathways and reactions for 2-methylnaphthalene, 1-methylnaphthalene, dibenzofuran, fluorene, phenanthrene, anthracene and pyrene catalyzed by peroxygenases from Agrocybe aegerita and Coprinellus radians (abbreviated as AaP and CrP). AaP hydroxylated the aromatic rings of all substrates tested at different positions, whereas CrP showed a limited capacity for aromatic ring-hydroxylation and did not hydroxylate phenanthrene but preferably oxygenated fluorene at the non-aromatic C9-carbon and methylnaphthalenes at the side chain. The results demonstrate for the first time the broad substrate specificity of fungal peroxygenases for polyaromatic compounds, and they are discussed in terms of their biocatalytic and environmental implications.

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Acknowledgments

Funding of this research is gratefully acknowledged to the Spanish Science and Technology Foundation (FECYT) and MICINN (grant to E. Aranda), the European Union (integrated project BIORENEW), the “Deutsches Bundesministerium für Bildung, Wissenschaft und Forschung” (BMBF; project 0313433D) and the “Deutsche Bundesstiftung Umwelt” (DBU; project 13225-32). Special thanks go to M. Kluge and M. Kinne for their analytical advice and C. Liers, M. Poraj-Kobielska and M. Pecyna for their interesting discussions. We thank U. Schneider and M. Brant for their excellent technical assistance.

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  1. Department of Environmental Biotechnology, International Graduate School of Zittau, Markt 23, 02763, Zittau, Germany

    Elisabet Aranda, René Ullrich & Martin Hofrichter

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  1. Elisabet Aranda
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  2. René Ullrich
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Correspondence to Elisabet Aranda.

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Aranda, E., Ullrich, R. & Hofrichter, M. Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases. Biodegradation 21, 267–281 (2010). https://doi.org/10.1007/s10532-009-9299-2

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