Cross-linked DNA generated by "bis-click" reactions with bis-functional azides: Site independent ligation of oligonucleotides via nucleobase alkynyl chains

Suresh S. Pujari, Hai Xiong, Frank Seela

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34 Scopus citations

Abstract

Template-free cross-linking of single-stranded DNA bearing octadiynyl side chains at the 7-position of 8-aza-7-deazapurine moieties with bisfunctional azides is reported employing a Cu(I)-catalyzed azide-alkyne "bis- click" reaction. Bis-adducts were formed when the bis-azide:oligonucleotide ratio was 1:1; monofunctionalization occurred when the ratio was 15:1. Four-stranded DNA consisting of two cross-linked duplexes was obtained after hydridization. Cross-linked duplexes are as stable as individual duplexes when ligation was introduced at terminal positions; ligation at a central position led to a slight duplex destabilization.

Original languageEnglish (US)
Pages (from-to)8693-8696
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number24
DOIs
StatePublished - Dec 17 2010

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