ArticleNature communications2016
Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids.
Article in Nature communications, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- The Diels-Alder Reaction as a Key Step in Natural Product Synthesis.Progress in the chemistry of organic natural products · 2026Review
- Recyclable Organic Redox Molecules for Sustainable Batteries.ChemSusChem · 2025Article
- Discovery and Theoretical Studies of Nonenzymatic Polyketide Dimerizations of Chaetophenols.Organic letters · 2025Article
- Exploring the Nonenzymatic Origin of Duclauxin-like Natural Products.Journal of natural products · 2024Article
- Engineering Streptomyces sp. CPCC 204095 for the targeted high-level production of isatropolone A by elucidating its pathway-specific regulatory mechanism.Microbial cell factories · 2024Article
- Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.Molecules (Basel, Switzerland) · 2024Article
- Heterologous expression of the crypticRSC advances · 2023Article
- Advances on the biosynthesis of pyridine rings.Engineering microbiology · 2023Review
- Isatropolone/isarubrolone CThe Journal of antibiotics · 2022Article
- Biomimetic Total Synthesis and Investigation of the Non-Enzymatic Chemistry of Oxazinin A.Angewandte Chemie (International ed. in English) · 2022Article
- Dihydroisatropolone C fromMolecules (Basel, Switzerland) · 2022Article
- Rubrolone production by Dactylosporangium vinaceum: biosynthesis, modulation and possible biological function.Applied microbiology and biotechnology · 2021Article
- Stable lead-halide perovskite quantum dots as efficient visible light photocatalysts for organic transformations.Nanoscale advances · 2021Article
- Characterization of a Novel Endophytic Actinomycete,Microorganisms · 2020Article
- Biosynthetic access to the rare antiarose sugarChemical science · 2020Article
- An Alkylpyrazine Synthesis Mechanism Involving l-Threonine-3-Dehydrogenase Describes the Production of 2,5-Dimethylpyrazine and 2,3,5-Trimethylpyrazine by Bacillus subtilis.Applied and environmental microbiology · 2019Article
- Biosynthesis of Tropolones in Streptomyces spp.: Interweaving Biosynthesis and Degradation of Phenylacetic Acid and Hydroxylations on the Tropone Ring.Applied and environmental microbiology · 2018Article
- α-Pyrone Derivatives from a Streptomyces Strain Resensitize Tamoxifen Resistance in Breast Cancer Cells.Natural products and bioprospecting · 2017Article
- Carpatizine, a novel bridged oxazine derivative generated by non-enzymatic reactions.Organic & biomolecular chemistry · 2017Article
- Production of Stealthin C Involves an S-N-Type Smiles Rearrangement.Journal of the American Chemical Society · 2017Article
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Authors and funding
10 authors.
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Abstract
The pyridine ring is a potent pharmacophore in alkaloid natural products. Nonetheless, its biosynthetic pathways are poorly understood. Rubrolones A and B are tropolone alkaloid natural products possessing a unique tetra-substituted pyridine moiety. Here, we report the gene cluster and propose a biosynthetic pathway for rubrolones, identifying a key intermediate that accumulates upon inactivation of sugar biosynthetic genes. Critically, this intermediate was converted to the aglycones of rubrolones by non-enzymatic condensation and cyclization with either ammonia or anthranilic acid to generate the respective pyridine rings. We propose that this non-enzymatic reaction occurs via hydrolysis of the key intermediate, which possesses a 1,5-dione moiety as an amine acceptor capable of cyclization. This study suggests that 1,5-dione moieties may represent a general strategy for pyridine ring biosynthesis, and more broadly highlights the utility of non-enzymatic diversification for exploring and expanding natural product chemical space.
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