Chemoselective covalent coupling of oligonucleotide probes to self-assembled monolayers.

TitleChemoselective covalent coupling of oligonucleotide probes to self-assembled monolayers.
Publication TypeJournal Article
Year of Publication2005
AuthorsDevaraj NK, Miller GP, Ebina W, Kakaradov B, Collman JP, Kool ET, Chidsey CED
JournalJ Am Chem Soc
Volume127
Issue24
Pagination8600-1
Date Published2005 Jun 22
ISSN0002-7863
KeywordsAmines, Copper, Oligonucleotide Probes, Oligonucleotides, Organometallic Compounds, Triazoles
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.

DOI10.1021/ja051462l
PubMed URLhttp://www.ncbi.nlm.nih.gov/pubmed/15954758?dopt=Abstract
PMCPMC3431914
Alternate TitleJ. Am. Chem. Soc.
PubMed ID15954758