ArticleAngewandte Chemie (International ed. in English)2021
Catalytic Control of Spiroketal Formation in Rubromycin Polyketide Biosynthesis.
Article in Angewandte Chemie (International ed. in English), 2021. 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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Who cites it
12 citing papers in PubMed, 20 citations in OpenAlex.
- Article
- Genome Mining-Guided Discovery of the Glycosylated Griseorhodin Congener Ruskamycin.Journal of natural products · 2026Article
- BisCEET: A Visual Browser for Biosynthetic Gene Clusters Aiding in the Identification of Natural Product Variants and Distinct Tailoring Enzymes.Journal of natural products · 2026Article
- A Hooker Oxygenase Archetype in Polyketide Biosynthesis Challenging the Baeyer-Villiger Monooxygenase Paradigm.Journal of the American Chemical Society · 2026Article
- A highly efficient heterologous expression platform to facilitate the production of microbial natural products in Streptomyces.Microbial cell factories · 2025Article
- Genome-mining-guided discovery of coumarubrin: A novel aminocoumarin-substituted rubromycin antibiotic.Journal of industrial microbiology & biotechnology · 2024Article
- Biosynthesis of the bacterial antibiotic 3,7-dihydroxytropolone through enzymatic salvaging of catabolic shunt products.Chemical science · 2024Article
- Biochemical and structural insights of multifunctional flavin-dependent monooxygenase FlsO1-catalyzed unexpected xanthone formation.Nature communications · 2022Article
- Isolation, biosynthesis, and biological activity of rubromycins derived from actinomycetes.Engineering microbiology · 2022Review
- An acetyltransferase controls the metabolic flux in rubromycin polyketide biosynthesis by direct modulation of redox tailoring enzymes.Chemical science · 2022Article
- Three Rings to Rule Them All: How Versatile Flavoenzymes Orchestrate the Structural Diversification of Natural Products.Biochemistry · 2022Article
- Catalytic Control of Spiroketal Formation in Rubromycin Polyketide Biosynthesis.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
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Abstract
The medically important bacterial aromatic polyketide natural products typically feature a planar, polycyclic core structure. An exception is found for the rubromycins, whose backbones are disrupted by a bisbenzannulated [5,6]-spiroketal pharmacophore that was recently shown to be assembled by flavin-dependent enzymes. In particular, a flavoprotein monooxygenase proved critical for the drastic oxidative rearrangement of a pentangular precursor and the installment of an intermediate [6,6]-spiroketal moiety. Here we provide structural and mechanistic insights into the control of catalysis by this spiroketal synthase, which fulfills several important functions as reductase, monooxygenase, and presumably oxidase. The enzyme hereby tightly controls the redox state of the substrate to counteract shunt product formation, while also steering the cleavage of three carbon-carbon bonds. Our work illustrates an exceptional strategy for the biosynthesis of stable chroman spiroketals.
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