This work was supported by the European community through the BioChemLig project.
Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media†
Article first published online: 30 APR 2014
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 23, pages 5872–5876, June 2, 2014
How to Cite
Bevilacqua, V., King, M., Chaumontet, M., Nothisen, M., Gabillet, S., Buisson, D., Puente, C., Wagner, A. and Taran, F. (2014), Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media. Angew. Chem. Int. Ed., 53: 5872–5876. doi: 10.1002/anie.201310671
- Issue published online: 30 MAY 2014
- Article first published online: 30 APR 2014
- Manuscript Revised: 6 MAR 2014
- Manuscript Received: 9 DEC 2013
- European community
- chemical biology;
- click chemistry;
The concept of chelation-assisted copper catalysis was employed for the development of new azides that display unprecedented reactivity in the copper(I)-catalyzed azide–alkyne [3+2] cycloaddition (CuAAC) reaction. Azides that bear strong copper-chelating moieties were synthesized; these functional groups allow the formation of azide copper complexes that react almost instantaneously with alkynes under diluted conditions. Efficient ligation occurred at low concentration and in complex media with only one equivalent of copper, which improves the biocompatibility of the CuAAC reaction. Furthermore, such a click reaction allowed the localization of a bioactive compound inside living cells by fluorescence measurements.