ArticleAngewandte Chemie (International ed. in English)2015
Macrodiolide formation by the thioesterase of a modular polyketide synthase.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Covalent warhead assembly in fostriecin biosynthesis involves malonylation-lactonisation by a bifunctional thioesterase and enzymatic demalonylation.Nature communications · 2026Article
- Article
- Establishing Selectivity Trends with Reactions of Thioesterases and Semi-Synthetic Polyketides.Journal of the American Chemical Society · 2025Article
- Streptomyces alleviate abiotic stress in plant by producing pteridic acids.Nature communications · 2023Article
- Current State-of-the-Art Toward Chemoenzymatic Synthesis of Polyketide Natural Products.Chembiochem : a European journal of chemical biology · 2023Review
- The Disorazole Z Family of Highly Potent Anticancer Natural Products from Sorangium cellulosum: Structure, Bioactivity, Biosynthesis, and Heterologous Expression.Microbiology spectrum · 2023Article
- In Vitro Biochemical Characterization of Excised Macrocyclizing Thioesterase Domains from Non-ribosomal Peptide Synthetases.Methods in molecular biology (Clifton, N.J.) · 2023Article
- Secondary Metabolites and Biosynthetic Gene Clusters Analysis of Deep-Sea Hydrothermal Vent-DerivedMarine drugs · 2022Article
- Elaiophylin Is a Potent Hsp90/ Cdc37 Protein Interface Inhibitor with K-Ras Nanocluster Selectivity.Biomolecules · 2021Article
- Biosynthetic Cyclization Catalysts for the Assembly of Peptide and Polyketide Natural Products.ChemCatChem · 2021Article
- Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition.Chemical science · 2020Article
- Biosynthesis of depsipeptides, or Depsi: The peptides with varied generations.Protein science : a publication of the Protein Society · 2020Review
- Natural Occurrence, Bioactivity and Biosynthesis of Elaiophylin Analogues.Molecules (Basel, Switzerland) · 2019Review
- Efomycins K and L From a Termite-AssociatedFrontiers in microbiology · 2019Article
- Trapping biosynthetic acyl-enzyme intermediates with encoded 2,3-diaminopropionic acid.Nature · 2019Article
- The Uncommon Enzymology of Cis-Acyltransferase Assembly Lines.Chemical reviews · 2017Review
- Accessing Nature's diversity through metabolic engineering and synthetic biology.F1000Research · 2016Review
- Iterative Mechanism of Macrodiolide Formation in the Anticancer Compound Conglobatin.Chemistry & biology · 2015Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Elaiophylin is an unusual C2 -symmetric antibiotic macrodiolide produced on a bacterial modular polyketide synthase assembly line. To probe the mechanism and selectivity of diolide formation, we sought to reconstitute ring formation in vitro by using a non-natural substrate. Incubation of recombinant elaiophylin thioesterase/cyclase with a synthetic pentaketide analogue of the presumed monomeric polyketide precursor of elaiophylin, specifically its N-acetylcysteamine thioester, produced a novel 16-membered C2 -symmetric macrodiolide. A linear dimeric thioester is an intermediate in ring formation, which indicates iterative use of the thioesterase active site in ligation and subsequent cyclization. Furthermore, the elaiophylin thioesterase acts on a mixture of pentaketide and tetraketide thioesters to give both the symmetric decaketide diolide and the novel asymmetric hybrid nonaketide diolide. Such thioesterases have potential as tools for the in vitro construction of novel diolides.
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