Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry

John C. Jewett, Carolyn R. Bertozzi

Research output: Contribution to journalArticle

73 Scopus citations

Abstract

Cyclooctyne-based probes that become fluorescent upon reaction with azides are important targets for real-time imaging of azide-labeled biomolecules. The concise synthesis of a coumarin-conjugated cyclooctyne, coumBARAC, that undergoes a 10-fold enhancement in fluorescence quantum yield upon triazole formation with organic azides is reported. The design principles embodied in coumBARAC establish a platform for generating fluorogenic cyclooctynes suited for biological imaging.

Original languageEnglish (US)
Pages (from-to)5937-5939
Number of pages3
JournalOrganic Letters
Volume13
Issue number22
DOIs
StatePublished - Nov 18 2011
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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