ArticleAngewandte Chemie (International ed. in English)2022
Alternative Benzoxazole Assembly Discovered in Anaerobic Bacteria Provides Access to Privileged Heterocyclic Scaffold.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- 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
- Multicomponent reactions (MCRs) yielding medicinally relevant rings: a recent update and chemical space analysis of the scaffolds.RSC advances · 2025Review
- Advances in the synthetic strategies of benzoxazoles using 2-aminophenol as a precursor: an up-to-date review.RSC advances · 2023Review
- Genomics-Driven Discovery of Benzoxazole Alkaloids from the Marine-DerivedMolecules (Basel, Switzerland) · 2023Article
- Alternative Benzoxazole Assembly Discovered in Anaerobic Bacteria Provides Access to Privileged Heterocyclic Scaffold.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Benzoxazole scaffolds feature prominently in diverse synthetic and natural product-derived pharmaceuticals. Our understanding of their bacterial biosynthesis is, however, limited to ortho-substituted heterocycles from actinomycetes. We report an overlooked biosynthetic pathway in anaerobic bacteria (typified in Clostridium cavendishii) that expands the benzoxazole chemical space to meta-substituted heterocycles and heralds a distribution beyond Actinobacteria. The first benzoxazoles from the anaerobic realm (closoxazole A and B) were elucidated by NMR and chemical synthesis. By genome editing in the native producer, heterologous expression in Escherichia coli, and systematic pathway dissection we show that closoxazole biosynthesis invokes an unprecedented precursor usage (3-amino-4-hydroxybenzoate) and manner of assembly. Synthetic utility was demonstrated by the precursor-directed biosynthesis of a tafamidis analogue. A bioinformatic survey reveals the pervasiveness of related gene clusters in diverse bacterial phyla.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.