ArticleJournal of the American Chemical Society2022
Probing the Mechanism of Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase.
Article in Journal of the American Chemical Society, 2022. 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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15 citing papers in PubMed, 25 citations in OpenAlex.
- Discovery and Biosynthesis of Sesquiterpene Polyketide Ester from an Atypical Terpene and Highly Reducing Polyketide Pathway.JACS Au · 2026Article
- Molecular Basis of α-Glycine C-H Activation by a Nonheme Fe(II)/2-Oxoglutarate Dioxygenase.Biochemistry · 2026Article
- A highly dynamic mononuclear non-heme iron enzyme for the two-step isonitrile biosynthesis.Nature communications · 2026Article
- Discovery of Isonitrile Lipopeptide Chalkophores from Pathogenic Mycobacteria.Journal of natural products · 2025Article
- Unusual O-H Activation-Initiated C-C Bond Cleavage Reaction by a Nonheme Fe Enzyme in Antifungal Nucleoside Biosynthesis.Journal of the American Chemical Society · 2025Article
- The Role of the Unusual 2-Tyr-1-carboxylate Non-heme Iron Motif in the Mechanism of N,N-Dimethylformamidase.ACS catalysis · 2025Article
- Studies of Isonitrile Synthases Help Elucidate the Mechanism of Isonitrile Installation.ACS catalysis · 2025Article
- Copper-chelating natural products.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2025Review
- Characterization of the Flavin-Dependent Monooxygenase Involved in the Biosynthesis of the Nocardiosis-Associated Polyketide†.Biochemistry · 2024Article
- Biosynthesis of isonitrile lipopeptides.Current opinion in chemical biology · 2024Review
- Biosynthesis of macrolactam antibiotics with β-amino acid polyketide starter units.The Journal of antibiotics · 2024Review
- Variation in biosynthesis and metal-binding properties of isonitrile-containing peptides produced by Mycobacteria versus Streptomyces.ACS catalysis · 2024Article
- Isonitrile biosynthesis by non-heme iron(II)-dependent oxidases/decarboxylases.Methods in enzymology · 2024Article
- Repurposing Iron- and 2-Oxoglutarate-Dependent Oxygenases to Catalyze Olefin Hydration.Angewandte Chemie (International ed. in English) · 2023Article
- Biosynthesis of Isonitrile Lipopeptide Metallophores from Pathogenic Mycobacteria.Biochemistry · 2023Article
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12 authors at 3 institutions in 1 country.
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Abstract
The isonitrile moiety is an electron-rich functionality that decorates various bioactive natural products isolated from diverse kingdoms of life. Isonitrile biosynthesis was restricted for over a decade to isonitrile synthases, a family of enzymes catalyzing a condensation reaction between l-Trp/l-Tyr and ribulose-5-phosphate. The discovery of ScoE, a non-heme iron(II) and α-ketoglutarate-dependent dioxygenase, demonstrated an alternative pathway employed by nature for isonitrile installation. Biochemical, crystallographic, and computational investigations of ScoE have previously been reported, yet the isonitrile formation mechanism remains obscure. In the present work, we employed in vitro biochemistry, chemical synthesis, spectroscopy techniques, and computational simulations that enabled us to propose a plausible molecular mechanism for isonitrile formation. Our findings demonstrate that the ScoE reaction initiates with C5 hydroxylation of (
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