Cross-linked DNA generated by "bis-click" reactions with bis-functional azides: site independent ligation of oligonucleotides via nucleobase alkynyl chains.
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.
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany.
Suresh S
SS
Pujari
Hai
H
Xiong
Frank
F
Seela
D000480:Alkynes / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D020029:Base Pairing; D001483:Base Sequence; D004247:DNA / Q000737:chemistry*; D004277:DNA, Single-Stranded / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*
D000480:Alkynes; D001372:Aza Compounds; D001386:Azides; D004277:DNA, Single-Stranded; D009841:Oligonucleotides; D011687:Purines; C064191:1H-imidazo(4,5-b)pyridine; D004247:DNA