ArticleAMB Express2013
Benzene oxygenation and oxidation by the peroxygenase of Agrocybe aegerita.
Article in AMB Express, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 64 citations in OpenAlex.
- Oxyfunctionalisation of anisole and its selected reaction products by unspecific peroxygenases.Biochemistry and biophysics reports · 2025Article
- Structure-function relationships in unspecific peroxygenases revealed by a comparative study of their action on the phenolic lignin monomer 4-propylguaiacol.Biotechnology for biofuels and bioproducts · 2025Article
- Identification of Key Active-Site Positions Controlling the Chemoselectivity of Aspergillus Brasiliensis Unspecific Peroxygenase.Chembiochem : a European journal of chemical biology · 2025Article
- DFT Mechanistic Investigation into Ni(II)-Catalyzed Hydroxylation of Benzene to Phenol by HInorganic chemistry · 2024Article
- Machine Learning Approaches Identify Chemical Features for Stage-Specific Antimalarial Compounds.ACS omega · 2023Article
- Oxygenating Biocatalysts for Hydroxyl Functionalisation in Drug Discovery and Development.ChemMedChem · 2022Review
- Peroxide-Mediated Oxygenation of Organic Compounds by Fungal Peroxygenases.Antioxidants (Basel, Switzerland) · 2022Review
- Structural and biochemical studies enlighten the unspecific peroxygenase from Hypoxylon sp. EC38 as an efficient oxidative biocatalyst.ACS catalysis · 2021Article
- Biocatalytic Syntheses of Antiplatelet Metabolites of the Thienopyridines Clopidogrel and Prasugrel Using Fungal Peroxygenases.Journal of fungi (Basel, Switzerland) · 2021Article
- Reactive force fields for modeling oxidative degradation of organic matter in geological formations.RSC advances · 2021Article
- A hydroquinone-specific screening system for directed P450 evolution.Applied microbiology and biotechnology · 2018Article
- Fungal Unspecific Peroxygenases Oxidize the Majority of Organic EPA Priority Pollutants.Frontiers in microbiology · 2017Article
- Will 1,2-dihydro-1,2-azaborine-based drugs resist metabolism by cytochrome P450 compound I?PeerJ · 2016Article
- Synthetic biosensors for precise gene control and real-time monitoring of metabolites.Nucleic acids research · 2015Article
- Directed evolution of unspecific peroxygenase from Agrocybe aegerita.Applied and environmental microbiology · 2014Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Aromatic peroxygenase (APO) is an extracellular enzyme produced by the agaric basidiomycete Agrocybe aegerita that catalyzes diverse peroxide-dependent oxyfunctionalization reactions. Here we describe the oxygenation of the unactivated aromatic ring of benzene with hydrogen peroxide as co-substrate. The optimum pH of the reaction was around 7 and it proceeded via an initial epoxide intermediate that re-aromatized in aqueous solution to form phenol. Identity of the epoxide intermediate as benzene oxide was proved by a freshly prepared authentic standard using GC-MS and LC-MS analyses. Second and third [per]oxygenation was also observed and resulted in the formation of further hydroxylation and following [per]oxidation products: hydroquinone and p-benzoquinone, catechol and o-benzoquinone as well as 1,2,4-trihydroxybenzene and hydroxy-p-benzoquinone, respectively. Using H218O2 as co-substrate and ascorbic acid as radical scavenger, inhibiting the formation of peroxidation products (e.g., p-benzoquinone), the origin of the oxygen atom incorporated into benzene or phenol was proved to be the peroxide. Apparent enzyme kinetic constants (kcat, Km) for the peroxygenation of benzene were estimated to be around 8 s-1 and 3.6 mM. These results raise the possibility that peroxygenases may be useful for enzymatic syntheses of hydroxylated benzene derivatives under mild conditions.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.