Surface functionalization using catalyst-free azide-alkyne cycloaddition.
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.
Department of Chemistry, Complex Carbohydrate Research Center, University of Georgia, Athens, 30602, United States.
Alexander
A
Kuzmin
Andrei
A
Poloukhtine
Margreet A
MA
Wolfert
Vladimir V
VV
Popik
D000480:Alkynes / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001392:Azocines / Q000737:chemistry*; D057930:Click Chemistry; D003500:Cyclization; D015394:Molecular Structure; D013499:Surface Properties
D000480:Alkynes; D001372:Aza Compounds; D001386:Azides; D001392:Azocines