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Hydroxylation of naphthalene by aromatic peroxygenase from Agrocybe aegerita proceeds via oxygen transfer from H2O2 and intermediary epoxidation

  • Agrocybe aegerita peroxidase/peroxygenase (AaP) is an extracellular fungal biocatalyst that selectively hydroxylates the aromatic ring of naphthalene. Under alkaline conditions, the reaction proceeds via the formation of an intermediary product with a molecular mass of 144 and a characteristic UV absorption spectrum (A max 210, 267, and 303 nm). The compound was semistable at pH 9 but spontaneously hydrolyzed under acidic conditions (pH <7) into 1-naphthol as major product and traces of 2-naphthol. Based on these findings and literature data, we propose naphthalene 1,2-oxide as the primary product of AaP-catalyzed oxygenation of naphthalene. Using 18O-labeled hydrogen peroxide, the origin of the oxygen atom transferred to naphthalene was proved to be the peroxide that acts both as oxidant (primary electron acceptor) and oxygen source.

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Metadaten
Author: Martin Kluge, René UllrichORCiD, Christoph Dolge, Katrin Scheibner, Martin HofrichterORCiD
URL:http://link.springer.com/article/10.1007%2Fs00253-008-1704-y
DOI:https://doi.org/10.1007/s00253-008-1704-y
ISSN:0175-7598
Title of the source (English):Applied Microbiology and Biotechnology
Document Type:Scientific journal article peer-reviewed
Language:English
Year of publication:2009
Tag:Hydroxylation; Naphthol; Oxygenation; P450; Peroxidase
Volume/Year:81
Issue number:6
First Page:1071
Last Page:1076
Faculty/Chair:Fakultät 2 Umwelt und Naturwissenschaften / FG Enzymtechnologie
Institution name at the time of publication:Fakultät für Naturwissenschaften (eHL) / Prof. Enzymtechnologie
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