10.1021/bc100306u.s001
Alexander Kuzmin
Alexander
Kuzmin
Andrei Poloukhtine
Andrei
Poloukhtine
Margreet A. Wolfert
Margreet A.
Wolfert
Vladimir V. Popik
Vladimir V.
Popik
Surface Functionalization Using Catalyst-Free Azide−Alkyne Cycloaddition
American Chemical Society
2010
surface
cycloaddition
reactive cyclooctyne
azide
variety
immobilization techniques work
ADIBO
molecule
ambient conditions
Surface Functionalization
PEG linker
2010-11-17 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Surface_Functionalization_Using_Catalyst_Free_Azide_Alkyne_Cycloaddition/2712262
The utility of catalyst-free azide−alkyne [3 + 2] cycloaddition for the immobilization of a variety of molecules onto a solid surface and microbeads was demonstrated. In this process, the surfaces are derivatized with aza-dibenzocyclooctyne (ADIBO) for the immobilization of azide-tagged substrates via a copper-free click reaction. Alternatively, ADIBO-conjugated molecules are anchored to the azide-derivatized surface. Both immobilization techniques work well in aqueous solutions and show excellent kinetics under ambient conditions. We report an efficient synthesis of aza-dibenzocyclooctyne (ADIBO), thus far the most reactive cyclooctyne in cycloaddition to azides. We also describe convenient methods for the conjugation of ADIBO with a variety of molecules directly or via a PEG linker.