FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2318609894> ?p ?o ?g. }

• W2318609894 endingPage "5432" @default.
• W2318609894 startingPage "5426" @default.
• W2318609894 abstract "The colibactins are hybrid polyketide–nonribosomal peptide natural products produced by certain strains of commensal and extraintestinal pathogenic Escherichia coli. The metabolites are encoded by the clb gene cluster as prodrugs termed precolibactins. clb+ E. coli induce DNA double-strand breaks in mammalian cells in vitro and in vivo and are found in 55–67% of colorectal cancer patients, suggesting that mature colibactins could initiate tumorigenesis. However, elucidation of their structures has been an arduous task as the metabolites are obtained in vanishingly small quantities (μg/L) from bacterial cultures and are believed to be unstable. Herein we describe a flexible and convergent synthetic route to prepare advanced precolibactins and derivatives. The synthesis proceeds by late-stage union of two complex precursors (e.g., 28 + 17 → 29a, 90%) followed by a base-induced double dehydrative cascade reaction to form two rings of the targets (e.g., 29a → 30a, 79%). The sequence has provided quantities of advanced candidate precolibactins that exceed those obtained by fermentation, and is envisioned to be readily scaled. These studies have guided a structural revision of the predicted metabolite precolibactin A (from 5a or 5b to 7) and have confirmed the structures of the isolated metabolites precolibactins B (3) and C (6). Synthetic precolibactin C (6) was converted to N-myristoyl-d-asparagine and its corresponding colibactin by colibactin peptidase ClbP. The synthetic strategy outlined herein will facilitate mechanism of action and structure–function studies of these fascinating metabolites, and is envisioned to accommodate the synthesis of additional (pre)colibactins as they are isolated." @default.
• W2318609894 created "2016-06-24" @default.
• W2318609894 creator A5001484132 @default.
• W2318609894 creator A5018028906 @default.
• W2318609894 creator A5051483771 @default.
• W2318609894 creator A5055878366 @default.
• W2318609894 date "2016-04-12" @default.
• W2318609894 modified "2023-10-18" @default.
• W2318609894 title "Convergent and Modular Synthesis of Candidate Precolibactins. Structural Revision of Precolibactin A" @default.
• W2318609894 cites W1715339469 @default.
• W2318609894 cites W1830002893 @default.
• W2318609894 cites W1842852267 @default.
• W2318609894 cites W1904975951 @default.
• W2318609894 cites W1966028491 @default.
• W2318609894 cites W1970481556 @default.
• W2318609894 cites W1978773870 @default.
• W2318609894 cites W1981333158 @default.
• W2318609894 cites W1986272790 @default.
• W2318609894 cites W1989413517 @default.
• W2318609894 cites W1996173530 @default.
• W2318609894 cites W2003545535 @default.
• W2318609894 cites W2011411661 @default.
• W2318609894 cites W2013573375 @default.
• W2318609894 cites W2020204355 @default.
• W2318609894 cites W2026897048 @default.
• W2318609894 cites W2052717138 @default.
• W2318609894 cites W2061499749 @default.
• W2318609894 cites W2075479850 @default.
• W2318609894 cites W2081567301 @default.
• W2318609894 cites W2085440721 @default.
• W2318609894 cites W2089643849 @default.
• W2318609894 cites W2100659414 @default.
• W2318609894 cites W2117691468 @default.
• W2318609894 cites W2160276070 @default.
• W2318609894 cites W2285561481 @default.
• W2318609894 cites W2322764356 @default.
• W2318609894 cites W2337529988 @default.
• W2318609894 doi "https://doi.org/10.1021/jacs.6b02276" @default.
• W2318609894 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/5049697" @default.
• W2318609894 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/27025153" @default.
• W2318609894 hasPublicationYear "2016" @default.
• W2318609894 type Work @default.
• W2318609894 sameAs 2318609894 @default.
• W2318609894 citedByCount "43" @default.
• W2318609894 countsByYear W23186098942016 @default.
• W2318609894 countsByYear W23186098942017 @default.
• W2318609894 countsByYear W23186098942018 @default.
• W2318609894 countsByYear W23186098942019 @default.
• W2318609894 countsByYear W23186098942020 @default.
• W2318609894 countsByYear W23186098942021 @default.
• W2318609894 countsByYear W23186098942022 @default.
• W2318609894 countsByYear W23186098942023 @default.
• W2318609894 crossrefType "journal-article" @default.
• W2318609894 hasAuthorship W2318609894A5001484132 @default.
• W2318609894 hasAuthorship W2318609894A5018028906 @default.
• W2318609894 hasAuthorship W2318609894A5051483771 @default.
• W2318609894 hasAuthorship W2318609894A5055878366 @default.
• W2318609894 hasBestOaLocation W23186098942 @default.
• W2318609894 hasConcept C104317684 @default.
• W2318609894 hasConcept C108215921 @default.
• W2318609894 hasConcept C14036430 @default.
• W2318609894 hasConcept C185592680 @default.
• W2318609894 hasConcept C2777379556 @default.
• W2318609894 hasConcept C2777477808 @default.
• W2318609894 hasConcept C2777763344 @default.
• W2318609894 hasConcept C2778635478 @default.
• W2318609894 hasConcept C35753019 @default.
• W2318609894 hasConcept C54355233 @default.
• W2318609894 hasConcept C547475151 @default.
• W2318609894 hasConcept C553450214 @default.
• W2318609894 hasConcept C55493867 @default.
• W2318609894 hasConcept C70721500 @default.
• W2318609894 hasConcept C71240020 @default.
• W2318609894 hasConcept C86803240 @default.
• W2318609894 hasConceptScore W2318609894C104317684 @default.
• W2318609894 hasConceptScore W2318609894C108215921 @default.
• W2318609894 hasConceptScore W2318609894C14036430 @default.
• W2318609894 hasConceptScore W2318609894C185592680 @default.
• W2318609894 hasConceptScore W2318609894C2777379556 @default.
• W2318609894 hasConceptScore W2318609894C2777477808 @default.
• W2318609894 hasConceptScore W2318609894C2777763344 @default.
• W2318609894 hasConceptScore W2318609894C2778635478 @default.
• W2318609894 hasConceptScore W2318609894C35753019 @default.
• W2318609894 hasConceptScore W2318609894C54355233 @default.
• W2318609894 hasConceptScore W2318609894C547475151 @default.
• W2318609894 hasConceptScore W2318609894C553450214 @default.
• W2318609894 hasConceptScore W2318609894C55493867 @default.
• W2318609894 hasConceptScore W2318609894C70721500 @default.
• W2318609894 hasConceptScore W2318609894C71240020 @default.
• W2318609894 hasConceptScore W2318609894C86803240 @default.
• W2318609894 hasFunder F4320337351 @default.
• W2318609894 hasFunder F4320337354 @default.
• W2318609894 hasIssue "16" @default.
• W2318609894 hasLocation W23186098941 @default.
• W2318609894 hasLocation W23186098942 @default.
• W2318609894 hasLocation W23186098943 @default.
• W2318609894 hasLocation W23186098944 @default.
• W2318609894 hasOpenAccess W2318609894 @default.

• next