Azide-alkyne "click" reaction performed on oligonucleotides with the universal nucleoside 7-octadiynyl-7-deaza-2'-deoxyinosine

Nucleic Acids Symp Ser (Oxf). 2008:(52):471-2. doi: 10.1093/nass/nrn239.

Abstract

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.

MeSH terms

  • DNA / chemistry
  • Fluorescent Dyes / chemistry
  • Inosine / analogs & derivatives*
  • Inosine / chemistry
  • Oligonucleotides / chemistry*

Substances

  • 7-deaza-2'-deoxyinosine
  • Fluorescent Dyes
  • Oligonucleotides
  • Inosine
  • DNA