Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 24, Pages 8693-8696Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101809w
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- ChemBiotech, Munster, Germany
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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.
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