ArticleProceedings of the National Academy of Sciences of the United States of America2010
Four-electron oxidation of p-hydroxylaminobenzoate to p-nitrobenzoate by a peroxodiferric complex in AurF from Streptomyces thioluteus.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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41 citing papers in PubMed, 88 citations in OpenAlex.
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- The Heme Oxygenase-Like Diiron Enzyme HrmI Reveals Altered Regulatory Mechanisms for Dioxygen Activation and Substrate N-Oxygenation.Journal of the American Chemical Society · 2025Article
- Heme Oxygenase-Like Metalloenzymes.Annual review of biochemistry · 2025Review
- Biocatalytic Strategies for Nitration Reactions.JACS Au · 2025Review
- Reconstitution of the Final Steps in the Biosynthesis of Valanimycin Reveals the Origin of Its Characteristic Azoxy Moiety.Angewandte Chemie (International ed. in English) · 2024Article
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- Ligand-Constraint-Induced Peroxide Activation for Electrophilic Reactivity.Angewandte Chemie (International ed. in English) · 2021Article
- Structure and assembly of the diiron cofactor in the heme-oxygenase-like domain of theProceedings of the National Academy of Sciences of the United States of America · 2021Article
- In Vitro Reconstitution Reveals a Central Role for the N-Oxygenase PvfB in (Dihydro)pyrazine-N-oxide and Valdiazen Biosynthesis.Angewandte Chemie (International ed. in English) · 2020Article
- A Peroxodiiron(III/III) Intermediate Mediating BothJournal of the American Chemical Society · 2020Article
- High-resolution iron X-ray absorption spectroscopic and computational studies of non-heme diiron peroxo intermediates.Journal of inorganic biochemistry · 2020Article
- Molecular mechanism of azoxy bond formation for azoxymycins biosynthesis.Nature communications · 2019Article
- Substrate-Triggered Formation of a Peroxo-FeJournal of the American Chemical Society · 2019Article
- Characterization of the flavin monooxygenase involved in biosynthesis of the antimalarial FR-900098.Organic & biomolecular chemistry · 2019Article
- Discovery of (Dihydro)pyrazine N-Oxides via Genome Mining in Pseudomonas.Organic letters · 2018Article
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4 authors at 1 institution in 1 country.
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Abstract
The nonheme di-iron oxygenase, AurF, converts p-aminobenzoate (Ar-NH(2), where Ar = 4-carboxyphenyl) to p-nitrobenzoate (Ar-NO(2)) in the biosynthesis of the antibiotic, aureothin, by Streptomyces thioluteus. It has been reported that this net six-electron oxidation proceeds in three consecutive, two-electron steps, through p-hydroxylaminobenzoate (Ar-NHOH) and p-nitrosobenzoate (Ar-NO) intermediates, with each step requiring one equivalent of O(2) and two exogenous reducing equivalents. We recently demonstrated that a peroxodiiron(III/III) complex (peroxo- -AurF) formed by addition of O(2) to the diiron(II/II) enzyme ( -AurF) effects the initial oxidation of Ar-NH(2), generating a mu-(oxo)diiron(III/III) form of the enzyme (mu-oxo- -AurF) and (presumably) Ar-NHOH. Here we show that peroxo- -AurF also oxidizes Ar-NHOH. Unexpectedly, this reaction proceeds through to the Ar-NO(2) final product, a four-electron oxidation, and produces -AurF, with which O(2) can combine to regenerate peroxo- -AurF. Thus, conversion of Ar-NHOH to Ar-NO(2) requires only a single equivalent of O(2) and (starting from -AurF or peroxo- -AurF) is fully catalytic in the absence of exogenous reducing equivalents, by contrast to the published stoichiometry. This novel type of four-electron N-oxidation is likely also to occur in the reaction sequences of nitro-installing di-iron amine oxygenases in the biosyntheses of other natural products.
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