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  • Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones.

Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones.

Journal of the American Chemical Society (2010-03-02)
John C Jewett, Ellen M Sletten, Carolyn R Bertozzi
ABSTRACT

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 biarylazacyclooctynone (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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Dibenzocyclooctyne-PEG4-biotin conjugate, for Copper-free Click Chemistry
Sigma-Aldrich
Dibenzocyclooctyne-PEG4-N-hydroxysuccinimidyl ester, ≥90%
Avanti
DSPE-PEG(2000)-DBCO, Avanti Research - A Croda Brand
Sigma-Aldrich
Dibenzocyclooctyne-PEG4-maleimide, for Copper-free Click Chemistry
Sigma-Aldrich
Dibenzocyclooctyne-PEG4-alcohol, for Copper-free Click Chemistry
Sigma-Aldrich
Sulfo-dibenzocyclooctyne-biotin conjugate, for Copper-free Click Chemistry
Avanti
DSPE-PEG(2000) Azide, Avanti Research - A Croda Brand 880228C
Avanti
DSPE-PEG(2000) Azide, Avanti Research - A Croda Brand, powder
Sigma-Aldrich
Dibenzocyclooctyne-PEG4-acid, for Copper-free Click Chemistry
Sigma-Aldrich
Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester, for Copper-free Click Chemistry
Sigma-Aldrich
Dibenzocyclooctyne-maleimide, for Copper-free Click Chemistry
Sigma-Aldrich
Dibenzocyclooctyne-acid, 95%, storage temp.:-20°C
Sigma-Aldrich
Dibenzocyclooctyne-amine, for Copper-free Click Chemistry
Sigma-Aldrich
Dibenzocyclooctyne-N-hydroxysuccinimidyl ester, for Copper-free Click Chemistry