title: Chemoselective covalent coupling of oligonucleotide probes to self-assembled monolayers.
abstract: 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.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
authors.forename: Neal K
authors.initials: NK
authors.lastname: Devaraj
authors.forename: Gregory P
authors.initials: GP
authors.lastname: Miller
authors.forename: Wataru
authors.initials: W
authors.lastname: Ebina
authors.forename: Boyko
authors.initials: B
authors.lastname: Kakaradov
authors.forename: James P
authors.initials: JP
authors.lastname: Collman
authors.forename: Eric T
authors.initials: ET
authors.lastname: Kool
authors.forename: Christopher E D
authors.initials: CE
authors.lastname: Chidsey
mesh_terms: 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
chemical_list: D000588:Amines; D015345:Oligonucleotide Probes; D009841:Oligonucleotides; D009942:Organometallic Compounds; D014230:Triazoles; D003300:Copper