Copper-chelating azides for efficient click conjugation reactions in complex media.
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.
CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif sur Yvette (France).
Valentina
V
Bevilacqua
Mathias
M
King
Manon
M
Chaumontet
Marc
M
Nothisen
Sandra
S
Gabillet
David
D
Buisson
Céline
C
Puente
Alain
A
Wagner
Frédéric
F
Taran
D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D017382:Reactive Oxygen Species
D001386:Azides; D017382:Reactive Oxygen Species; D003300:Copper
bioconjugation; chemical biology; click chemistry; copper