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

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

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...

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Veröffentlicht in:Organic & biomolecular chemistry 2011-01, Vol.9 (5), p.1381-1388
Hauptverfasser: Jørgensen, Anna S, Shaikh, Khalil I, Enderlin, Gerald, Ivarsen, Elise, Kumar, Surender, Nielsen, Poul
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Sprache:eng
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Chemical Sciences
Nucleic Acid Conformation
Nucleic Acids - chemistry
Nucleosides - chemical synthesis
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container_end_page 1388
container_issue 5
container_start_page 1381
container_title Organic & biomolecular chemistry
container_volume 9
creator Jørgensen, Anna S
Shaikh, Khalil I
Enderlin, Gerald
Ivarsen, Elise
Kumar, Surender
Nielsen, Poul
description 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.
doi_str_mv 10.1039/c0ob00438c
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subjects Chemical Sciences
Nucleic Acid Conformation
Nucleic Acids - chemistry
Nucleosides - chemical synthesis
title The synthesis of double-headed nucleosides by the CuAAC reaction and their effect in secondary nucleic acid structures
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