ArticleNature chemistry2021
Glycine-derived nitronates bifurcate to O-methylation or denitrification in bacteria.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Review
- A mild and efficient synthesis ofRSC advances · 2025Article
- Cofactorless oxygenases guide anthraquinone-fused enediyne biosynthesis.Nature chemical biology · 2024Article
- Activity assays of NnlA homologs suggest the natural productBeilstein journal of organic chemistry · 2024Article
- Isonitrile biosynthesis by non-heme iron(II)-dependent oxidases/decarboxylases.Methods in enzymology · 2024Article
- Heterologous Production and Biosynthesis of Threonine-16:0dioic acids with a Hydroxamate Moiety.Journal of natural products · 2023Article
- Taxonomic Positions and Secondary Metabolite-Biosynthetic Gene Clusters of Akazaoxime- and Levantilide-Producers.Life (Basel, Switzerland) · 2023Article
- Probing the Mechanism of Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase.Journal of the American Chemical Society · 2022Article
- Article
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2 authors.
Funding
Abstract
Natural products with rare functional groups are likely to be constructed by unique biosynthetic enzymes. One such rare functional group is the O-methyl nitronate, which can undergo [3 + 2] cycloaddition reactions with olefins in mild conditions. O-methyl nitronates are found in some natural products; however, how such O-methyl nitronates are assembled biosynthetically is unknown. Here we show that the assembly of the O-methyl nitronate in the natural product enteromycin carboxamide occurs via activation of glycine on a peptidyl carrier protein, followed by reaction with a diiron oxygenase to give a nitronate intermediate and then with a methyltransferase to give an O-methyl nitronate. Guided by the discovery of this pathway, we then identify related cryptic biosynthetic gene cassettes in other bacteria and show that these alternative gene cassettes can, instead, facilitate oxidative denitrification of glycine-derived nitronates. Altogether, our work reveals bifurcating pathways from a central glycine-derived nitronate intermediate in bacteria.
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