Azide-alkyne "click" reaction performed on oligonucleotides with the universal nucleoside 7-octadiynyl-7-deaza-2'-deoxyinosine.
Oligonucleotides containing 7-substituted 7-deaza-2'- deoxyinosine derivatives bearing alkynyl groups were prepared. The octa-1,7-diynyl derivative was functionalized with the non-fluorescent 3- azidocoumarin by the Huisgen-Sharpless-Meldal cycloaddition to afford a highly fluorescent oligonucleotide conjugate. The ambiguous base pairing character and the clickable side chain allows the incorporation of almost any reporter molecule to DNA.
Ming
Xin
X
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstr. 11, 48149 Münster, Germany.
Leonard
Peter
P
Heindl
Dieter
D
Seela
Frank
F
D004247:DNA / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D007288:Inosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009841:Oligonucleotides / Q000737:chemistry*
C533718:7-deaza-2'-deoxyinosine; D005456:Fluorescent Dyes; D009841:Oligonucleotides; D007288:Inosine; D004247:DNA