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

Org Biomol Chem. 2011 Mar 7;9(5):1381-8. doi: 10.1039/c0ob00438c. Epub 2011 Jan 5.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Nucleic Acid Conformation*
  • Nucleic Acids / chemistry*
  • Nucleosides / chemical synthesis*

Substances

  • Nucleic Acids
  • Nucleosides