Bioorthogonal Fluoride-Responsive Azide and Alkynyl Pyridinium Click Cycloaddition in Vitro and in Live Cells.

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  • Additional Information
    • Source:
      Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: MEDLINE
    • Publication Information:
      Original Publication: Washington, DC : American Chemical Society, c1999-
    • Subject Terms:
      Fluorides* ; Azides*; Cycloaddition Reaction ; Proteins ; Alkynes ; Click Chemistry
    • Abstract:
      The copper-free azide-alkyne cycloaddition was broadly applied in numerous research fields. Herein, we report a facile Cu-free click reaction utilizing fluoride-responsive azide and alkynyl pyridinium cycloaddition at ambient temperatures in aqueous media. The reactivity of alkynyl pyridinium was successfully masked by a silyl-protecting group at the alkyne group, and the deprotection could be readily achieved with the addition of F - , which renders the reactivity. The substrates were readily synthesized and proven to be stable at the bench. This bioorthogonal fluoride-responsive click reaction was then successfully employed in peptide modification, protein labeling, and cell imaging, suggesting its potential in various applications.
    • Accession Number:
      Q80VPU408O (Fluorides)
      0 (Azides)
      0 (Proteins)
      0 (Alkynes)
    • Publication Date:
      Date Created: 20230601 Date Completed: 20230619 Latest Revision: 20231205
    • Publication Date:
      20240829
    • Accession Number:
      10.1021/acs.orglett.3c01403
    • Accession Number:
      37260266