ArticleNature communications2018
Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Targeted Inactivation of anMarine drugs · 2026Article
- Study about fluostatins: efficient preparation of fluostatin A and discovery of fluostatin derivatives from Streptomyces sp. TA-3391.The Journal of antibiotics · 2025Article
- Unravelling key enzymatic steps in C-ring cleavage during angucycline biosynthesis.Communications chemistry · 2023Article
- On the Abundance and Stability of Diazo-Containing Secondary Metabolites: Enantioselective Synthesis of (-)-Nenestatin A.Organic letters · 2023Article
- Investigation of the Biosynthetic Mechanism of Bipentaromycin Featuring an Unprecedented Cyclic Head-to-Tail Dimeric Scaffold.JACS Au · 2023Article
- Biochemical and structural insights of multifunctional flavin-dependent monooxygenase FlsO1-catalyzed unexpected xanthone formation.Nature communications · 2022Article
- Flavin-enabled reductive and oxidative epoxide ring opening reactions.Nature communications · 2022Article
- Tripodalsporormielones A-C, unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems.Acta pharmaceutica Sinica. B · 2021Article
- Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis.Angewandte Chemie (International ed. in English) · 2021Article
- Himalaquinones A-G, Angucyclinone-Derived Metabolites Produced by the Himalayan IsolateJournal of natural products · 2021Article
- Native and non-native host assessment towards metabolic pathway reconstructions of plant natural products.Biotechnology reports (Amsterdam, Netherlands) · 2021Review
- Structure Revision of the Lomaiviticins.Journal of the American Chemical Society · 2021Article
- Mutation of an atypical oxirane oxyanion hole improves regioselectivity of the α/β-fold epoxide hydrolase Alp1U.The Journal of biological chemistry · 2020Article
- Understand the Specific Regio- and Enantioselectivity of Fluostatin Conjugation in the Post-Biosynthesis.Biomolecules · 2020Article
- Chimeric 6-methylsalicylic acid synthase with domains of acyl carrier protein and methyltransferase from Pseudallescheria boydii shows novel biosynthetic activity.Microbial biotechnology · 2019Article
- Albumycin, a new isoindolequinone from Streptomyces albus J1074 harboring the fluostatin biosynthetic gene cluster.The Journal of antibiotics · 2019Article
- Discovery of Stealthin Derivatives and Implication of the Amidotransferase FlsN3 in the Biosynthesis of Nitrogen-Containing Fluostatins.Marine drugs · 2019Article
- Dalmanol biosyntheses require coupling of two separate polyketide gene clusters.Chemical science · 2019Article
- Angucycline Glycosides from an Intertidal Sediments StrainMarine drugs · 2018Article
- Marine Bacterial Aromatic Polyketides From Host-Dependent Heterologous Expression and Fungal Mode of Cyclization.Frontiers in chemistry · 2018Article
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12 authors.
Funding
Abstract
Lomaiviticin A and difluostatin A are benzofluorene-containing aromatic polyketides in the atypical angucycline family. Although these dimeric compounds are potent antitumor agents, how nature constructs their complex structures remains poorly understood. Herein, we report the discovery of a number of fluostatin type dimeric aromatic polyketides with varied C-C and C-N coupling patterns. We also demonstrate that these dimers are not true secondary metabolites, but are instead derived from non-enzymatic deacylation of biosynthetic acyl fluostatins. The non-enzymatic deacylation proceeds via a transient quinone methide like intermediate which facilitates the subsequent C-C/C-N coupled dimerization. Characterization of this unusual property of acyl fluostatins explains how dimerization takes place, and suggests a strategy for the assembly of C-C and C-N coupled aromatic polyketide dimers. Additionally, a deacylase FlsH was identified which may help to prevent accumulation of toxic quinone methides by catalyzing hydrolysis of the acyl group.
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