ArticleNature communications2019
Molecular mechanism of azoxy bond formation for azoxymycins biosynthesis.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
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- Structural Basis for the Catalytic Mechanism of ATP-Dependent Diazotase CmaA6.Angewandte Chemie (International ed. in English) · 2025Article
- Access to Nitrogen-nitrogen Bond-Containing Heterocycles Through Substrate Promiscuity of Piperazate Synthases.ACS catalysis · 2025Article
- A new heme enzyme family forms hydrazine groups in diverse biosynthetic pathways.bioRxiv : the preprint server for biology · 2025Article
- Diverse N-Oxidation of Primary Aromatic Amines Controlled by Engineered P450 Peroxizyme Variants Facilitated by Dual-Functional Small Molecule.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Recent Developments and Challenges in the Enzymatic Formation of Nitrogen-Nitrogen Bonds.ACS catalysis · 2025Review
- Unspecific peroxygenase enabled formation of azoxy compounds.Nature communications · 2024Article
- Genome Mining for Diazo-Synthesis-Related Genes inBiomolecules · 2024Article
- 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
- Unlocking mild-condition benzene ring contraction using nonheme diironChemical science · 2023Article
- A high activity mesoporous Pt@KIT-6 nanocomposite for selective hydrogenation of halogenated nitroarenes in a continuous-flow microreactor.Nanoscale advances · 2023Article
- Tistrellabactins A and B Are PhotoreactiveJournal of natural products · 2023Article
- A platform for distributed production of synthetic nitrated proteins in live bacteria.Nature chemical biology · 2023Article
- Deciphering chloramphenicol biotransformation mechanisms and microbial interactions via integrated multi-omics and cultivation-dependent approaches.Microbiome · 2022Article
- Directed Evolution of a Nonheme Diiron N-oxygenase AzoC for Improving Its Catalytic Efficiency toward Nitrogen Heterocycle Substrates.Molecules (Basel, Switzerland) · 2022Article
- New azodyrecins identified by a genome mining-directed reactivity-based screening.Beilstein journal of organic chemistry · 2022Article
- Activation and Characterization of Lanthomicins A-C by Promoter Engineering inFrontiers in microbiology · 2022Article
- Molecular basis of enzymatic nitrogen-nitrogen formation by a family of zinc-binding cupin enzymes.Nature communications · 2021Article
- Glycine-derived nitronates bifurcate to O-methylation or denitrification in bacteria.Nature chemistry · 2021Article
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6 authors.
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Abstract
Azoxy bond is an important chemical bond and plays a crucial role in high energy density materials. However, the biosynthetic mechanism of azoxy bond remains enigmatic. Here we report that the azoxy bond biosynthesis of azoxymycins is an enzymatic and non-enzymatic coupling cascade reaction. In the first step, nonheme diiron N-oxygenase AzoC catalyzes the oxidization of amine to its nitroso analogue. Redox coenzyme pairs then facilitate the mutual conversion between nitroso group and hydroxylamine via the radical transient intermediates, which efficiently dimerize to azoxy bond. The deficiency of nucleophilic reactivity in AzoC is proposed to account for the enzyme's non-canonical oxidization of amine to nitroso product. Free nitrogen radicals induced by coenzyme pairs are proposed to be responsible for the efficient non-enzymatic azoxy bond formation. This mechanism study will provide molecular basis for the biosynthesis of azoxy high energy density materials and other valuable azoxy chemicals.
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