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Issue 5, 2011
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The synthesis of double-headed nucleosides by the CuAAC reaction and their effect in secondary nucleic acid structures

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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.

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

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Supplementary files

Article information


Submitted
16 Jul 2010
Accepted
02 Nov 2010
First published
05 Jan 2011

Org. Biomol. Chem., 2011,9, 1381-1388
Article type
Paper

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

A. S. Jørgensen, K. I. Shaikh, G. Enderlin, E. Ivarsen, S. Kumar and P. Nielsen, Org. Biomol. Chem., 2011, 9, 1381
DOI: 10.1039/C0OB00438C

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