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Copper‐Chelating Azides for Efficient Click Conjugation Reactions in Complex Media
Author(s) -
Bevilacqua Valentina,
King Mathias,
Chaumontet Ma,
Nothisen Marc,
Gabillet Sandra,
Buisson David,
Puente Céline,
Wagner Alain,
Taran Frédéric
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201310671
Subject(s) - click chemistry , cycloaddition , copper , azide , chemistry , chelation , combinatorial chemistry , alkyne , reactivity (psychology) , catalysis , biocompatibility , polymer chemistry , photochemistry , organic chemistry , medicine , alternative medicine , pathology
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.