Chemoselective covalent coupling of oligonucleotide probes to self-assembled monolayers.
A chemoselective route to routinely and rapidly attach oligonucleotide probes to well-defined surfaces is presented. Cu(I) tris(benzyltriazolylmethyl)amine-catalyzed coupling of terminal acetylenes to azides on a self-assembled monolayer is used instead of traditional nucleophilic-electrophilic coupling reactions. The reaction proceeds well even in the presence of purposely introduced nucleophilic and electrophilic impurities. The density of oligonucleotide probes can be controlled by controlling the amount of azide functionality. Although most of our work was done on gold surfaces, this technique should be readily applicable to any surface on which an azide-containing monolayer can be assembled as we have preliminarily demonstrated by derivatizing azidotrimethoxysilane-modified glass slides with fluorescein-containing oligonucleotides.
Devaraj
Neal K
NK
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Miller
Gregory P
GP
Ebina
Wataru
W
Kakaradov
Boyko
B
Collman
James P
JP
Kool
Eric T
ET
Chidsey
Christopher E D
CE
D000588:Amines / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D015345:Oligonucleotide Probes / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry
D000588:Amines; D015345:Oligonucleotide Probes; D009841:Oligonucleotides; D009942:Organometallic Compounds; D014230:Triazoles; D003300:Copper