Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones

John C Jewett, Ellen M. Sletten, Carolyn R. Bertozzi

Research output: Contribution to journalArticle

405 Citations (Scopus)

Abstract

"Chemical equation presented" Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole product without the need for a toxic catalyst. Here we describe a iarylazacyclooctynone (BARAC) that has exceptional reaction kinetics and whose synthesis is designed to be both modular and scalable. We employed BARAC for live cell fluorescence imaging of azide-labeled glycans. The high signal-to-background ratio obtained using nanomolar concentrations of BARAC obviated the need for washing steps. Thus, BARAC is a promising reagent for in vivo imaging.

Original languageEnglish (US)
Pages (from-to)3688-3690
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number11
DOIs
StatePublished - Mar 24 2010
Externally publishedYes

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Click Chemistry
Azides
Biological Phenomena
Imaging techniques
Triazoles
Alkynes
Poisons
Optical Imaging
Washing
Reaction kinetics
Polysaccharides
Chemical reactions
Fluorescence
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones. / Jewett, John C; Sletten, Ellen M.; Bertozzi, Carolyn R.

In: Journal of the American Chemical Society, Vol. 132, No. 11, 24.03.2010, p. 3688-3690.

Research output: Contribution to journalArticle

Jewett, John C ; Sletten, Ellen M. ; Bertozzi, Carolyn R. / Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones. In: Journal of the American Chemical Society. 2010 ; Vol. 132, No. 11. pp. 3688-3690.
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