The synthesis of double-headed nucleosides by the CuAAC reaction and their effect in secondary nucleic acid structures

Anna Søndergaard Jørgensen, Khalil Isak Shaikh, Gerald Enderlin, Elise Ivarsen, Surender Kumar, Poul Nielsen

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review


Four double-headed nucleosides were prepared by the CuAAC reaction. Hereby, a triazole-containing linker connects an additional thymine or adenine to the 2´-position of 2´-deoxyuridine, a thymine to the 5´-position of thymidine and a thymine to the 6¢-position of an LNA-thymidine monomer. Whereas no
conclusive recognition effects of the additional thymines were found when introduced in LNA or at the 5´-position, both thymine and adenine in the 2´-position were found to stabilise three-way junctions in
both dsDNA and DNA:RNA contexts and to give cross-strand interactions in a DNA-duplex, when specifically introduced in a so-called (+1)-zipper motif.
TidsskriftOrganic & Biomolecular Chemistry
Sider (fra-til)1381 - 1388
Antal sider8
StatusUdgivet - 2011