ArticleNature chemistry2019
Synthesis and reactivity of precolibactin 886.
Article in Nature chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Synthesis and Biological Evaluation of Colibactin Derivatives.ACS chemical biology · 2026Article
- Colibactin produced by a honeybee symbiont defends against pathogens and shapes the gut community.bioRxiv : the preprint server for biology · 2025Article
- The specificity and structure of DNA cross-linking by the gut bacterial genotoxin colibactin.Science (New York, N.Y.) · 2025Article
- The specificity and structure of DNA crosslinking by the gut bacterial genotoxin colibactin.bioRxiv : the preprint server for biology · 2025Article
- Genome-scale CRISPR/Cas9 screening reveals the role ofmSphere · 2025Article
- Bacterial small molecule metabolites implicated in gastrointestinal cancer development.Nature reviews. Microbiology · 2025Review
- Repair of genomic interstrand crosslinks.DNA repair · 2024Review
- Structure Elucidation of Secondary Metabolites: Current Frontiers and Lingering Pitfalls.Accounts of chemical research · 2023Article
- Chemoselective bicyclobutane-based mass spectrometric detection of biological thiols uncovers human and bacterial metabolites.Chemical science · 2023Article
- Enantioselective Total Synthesis of (+)-KB343.Journal of the American Chemical Society · 2023Article
- Delivery, structure, and function of bacterial genotoxins.Virulence · 2022Review
- Polycarcin V induces DNA-damage response and enables the profiling of DNA-binding proteins.National science review · 2022Article
- Commensal microbiota from patients with inflammatory bowel disease produce genotoxic metabolites.Science (New York, N.Y.) · 2022Article
- The microbiome-product colibactin hits unique cellular targets mediating host-microbe interaction.Frontiers in pharmacology · 2022Review
- Colibactin in avian pathogenicVirulence · 2021Article
- Article
- On the Stability and Spectroscopic Properties of 5-Hydroxyoxazole-4-carboxylic Acid Derivatives.Organic letters · 2021Article
- Stool pattern is associated with not only the prevalence of tumorigenic bacteria isolated from fecal matter but also plasma and fecal fatty acids in healthy Japanese adults.BMC microbiology · 2021Article
- Insights into evolution and coexistence of the colibactin- and yersiniabactin secondary metabolite determinants in enterobacterial populations.Microbial genomics · 2021Article
- The Polyphosphate Kinase of Escherichia coli Is Required for Full Production of the Genotoxin Colibactin.mSphere · 2020Article
Corrections and comments
- Erratum issued
Authors and funding
6 authors.
Funding
Abstract
The clb gene cluster encodes the biosynthesis of metabolites known as precolibactins and colibactins. The clb pathway is found in gut commensal Escherichia coli, and clb metabolites are thought to initiate colorectal cancer via DNA crosslinking. Here we report confirmation of the structural assignment of the complex clb product precolibactin 886 via a biomimetic synthetic pathway. We show that an α-ketoimine linear precursor undergoes spontaneous cyclization to precolibactin 886 on HPLC purification. Studies of this α-ketoimine and the related α-dicarbonyl revealed that these compounds are unexpectedly susceptible to nucleophilic cleavage under mildly basic conditions. This cleavage pathway forms other known clb metabolites or biosynthetic intermediates and explains the difficulties in isolating fully mature biosynthetic products. This cleavage also accounts for a recently identified colibactin-adenine adduct. The colibactin peptidase ClbP deacylates synthetic precolibactin 886 to form a non-genotoxic pyridone, which suggests precolibactin 886 lies off the path of the major biosynthetic route.
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