ArticleAngewandte Chemie (International ed. in English)2020
Quinolactacin Biosynthesis Involves Non-Ribosomal-Peptide-Synthetase-Catalyzed Dieckmann Condensation to Form the Quinolone-γ-lactam Hybrid.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 28 citations in OpenAlex.
- Discovery of Pyranoquinolone Diterpenoids Biosynthesized through Oxidative Indole Rearrangement and Atypical Terpene Cyclization.Journal of the American Chemical Society · 2026Article
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- Discovery and Biosynthetic Interrogation of a Cobalt-Containing Terpene-Polyketide-Nonribosomal Peptide Tribrid with Anticoronavirus Activity.Journal of the American Chemical Society · 2025Article
- Anti-Inflammatory Secondary Metabolites fromMarine drugs · 2025Article
- Enzymatic Ring Contraction for the Biosynthesis of Sulfur-Containing Cyclopentachromone.Journal of the American Chemical Society · 2025Article
- Recent Advances in the Synthesis and Biological Activities of Quinolactacin and its Derivatives: A Comprehensive Review.Current organic synthesis · 2025Review
- Biosynthesis of a clickable pyoverdine via in vivo enzyme engineering of an adenylation domain.Microbial cell factories · 2024Article
- Novel cuproptosis metabolism-related molecular clusters and diagnostic signature for Alzheimer's disease.Frontiers in molecular biosciences · 2024Article
- Unraveling the biosynthesis of penicillenols by genome mining PKS-NRPS gene clusters inAIChE journal. American Institute of Chemical Engineers · 2022Article
- Total Heterologous Biosynthesis of Fungal Natural Products inJournal of natural products · 2022Review
- Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions.ACS omega · 2021Article
- Engineered Biosynthesis of Fungal 4-Quinolone Natural Products.Organic letters · 2020Article
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5 authors at 1 institution in 1 country.
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Abstract
Quinolactacins are novel fungal alkaloids that feature a quinolone-γ-lactam hybrid, which is a potential pharmacophore for the treatment of cancer and Alzheimer's disease. Herein, we report the identification of the quinolactacin A2 biosynthetic gene cluster and elucidate the enzymatic basis for the formation of the quinolone-γ-lactam structure. We reveal an unusual β-keto acid (N-methyl-2-aminobenzoylacetate) precursor that is derived from the primary metabolite l-kynurenine via methylation, oxidative decarboxylation, and amide hydrolysis reactions. In vitro assays reveal two single-module non-ribosomal peptide synthetases (NRPs) that incorporate the β-keto acid and l-isoleucine, followed by Dieckmann condensation, to form the quinolone-γ-lactam. Notably, the bioconversion from l-kynurenine to the β-keto acid is a unique strategy employed by nature to decouple R*-domain-containing NRPS from the polyketide synthase (PKS) machinery, expanding the paradigm for the biosynthesis of quinolone-γ-lactam natural products via Dieckmann condensation.
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