Journal
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
Volume 81, Issue 6, Pages 1071-1076Publisher
SPRINGER
DOI: 10.1007/s00253-008-1704-y
Keywords
Peroxidase; Oxygenation; Hydroxylation; P450; Naphthol
Categories
Funding
- European Union
- German Ministry of Education and Research [0313433D]
- German Environmental Foundation [13225-32]
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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 O-18-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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