ArticleAngewandte Chemie (International ed. in English)2020
The Biosynthesis of the Benzoxazole in Nataxazole Proceeds via an Unstable Ester and has Synthetic Utility.
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 10 papers.
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Who cites it
10 citing papers in PubMed, 35 citations in OpenAlex.
- Goondoxazoles A-C: Anthelmintic Spiroketal Polyketide Alkaloids and Other Benzoxazoles from Australian Pasture Soil-DerivedAntibiotics (Basel, Switzerland) · 2026Article
- Integrated genome mining and molecular networking uncover the biosynthetic potential of a novel mangrove-derived strain Streptomyces sp. B1866.BMC genomics · 2025Article
- Discovery and In Vitro Reconstitution of Closoxazole Biosynthesis from Pyxidicoccus fallax.Chembiochem : a European journal of chemical biology · 2025Article
- Genomics-Driven Discovery of Benzoxazole Alkaloids from the Marine-DerivedMolecules (Basel, Switzerland) · 2023Article
- Genome Mining Enabled by Biosynthetic Characterization Uncovers a Class of Benzoxazolinate-Containing Natural Products in Diverse Bacteria.Angewandte Chemie (International ed. in English) · 2022Article
- Alternative Benzoxazole Assembly Discovered in Anaerobic Bacteria Provides Access to Privileged Heterocyclic Scaffold.Angewandte Chemie (International ed. in English) · 2022Article
- A Structural Perspective of Reps from CRESS-DNA Viruses and Their Bacterial Plasmid Homologues.Viruses · 2021Article
- Article
- Aryl Coenzyme A Ligases, a Subfamily of the Adenylate-Forming Enzyme Superfamily.Applied and environmental microbiology · 2021Review
- The Biosynthesis of the Benzoxazole in Nataxazole Proceeds via an Unstable Ester and has Synthetic Utility.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
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Abstract
Heterocycles, a class of molecules that includes oxazoles, constitute one of the most common building blocks in current pharmaceuticals and are common in medicinally important natural products. The antitumor natural product nataxazole is a model for a large class of benzoxazole-containing molecules that are made by a pathway that is not characterized. We report structural, biochemical, and chemical evidence that benzoxazole biosynthesis proceeds through an ester generated by an ATP-dependent adenylating enzyme. The ester rearranges via a tetrahedral hemiorthoamide to yield an amide, which is a shunt product and not, as previously thought, an intermediate in the pathway. A second zinc-dependent enzyme catalyzes the formation of hemiorthoamide from the ester but, by shuttling protons, the enzyme eliminates water, a reverse hydrolysis reaction, to yield the benzoxazole and avoids the amide. These insights have allowed us to harness the pathway to synthesize a series of novel halogenated benzoxazoles.
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