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

John C Jewett, Carolyn R. Bertozzi

Research output: Contribution to journalArticle

68 Citations (Scopus)

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

Fingerprint

azides (organic)
Click Chemistry
Azides
platforms
chemistry
fluorescence
augmentation
probes
synthesis
Imaging techniques
Triazoles
Biomolecules
Quantum yield
Fluorescent Dyes
Fluorescence

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry. / Jewett, John C; Bertozzi, Carolyn R.

In: Organic Letters, Vol. 13, No. 22, 18.11.2011, p. 5937-5939.

Research output: Contribution to journalArticle

Jewett, John C ; Bertozzi, Carolyn R. / Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry. In: Organic Letters. 2011 ; Vol. 13, No. 22. pp. 5937-5939.
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