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

doi:10.1039/c0ob00438c

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 tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstrakt

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.

Originalsprog	Engelsk
Tidsskrift	Organic & Biomolecular Chemistry
Vol/bind	9
Sider (fra-til)	1381 - 1388
Antal sider	8
ISSN	1477-0520
DOI	https://doi.org/10.1039/c0ob00438c
Status	Udgivet - 2011

Dokumenter og links

10.1039/c0ob00438c

Citationsformater

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

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.",

author = "J{\o}rgensen, {Anna S{\o}ndergaard} and Shaikh, {Khalil Isak} and Gerald Enderlin and Elise Ivarsen and Surender Kumar and Poul Nielsen",

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The synthesis of double-headed nucleosides by the CuAAC reaction and their effect in secondary nucleic acid structures. / Jørgensen, Anna Søndergaard; Shaikh, Khalil Isak; Enderlin, Gerald; Ivarsen, Elise; Kumar, Surender ; Nielsen, Poul.

I: Organic & Biomolecular Chemistry, Bind 9, 2011, s. 1381 - 1388.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

TY - JOUR

T1 - The synthesis of double-headed nucleosides by the CuAAC reaction and their effect in secondary nucleic acid structures

AU - Jørgensen, Anna Søndergaard

AU - Shaikh, Khalil Isak

AU - Enderlin, Gerald

AU - Ivarsen, Elise

AU - Kumar, Surender

AU - Nielsen, Poul

PY - 2011

Y1 - 2011

N2 - 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.

AB - 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.

U2 - 10.1039/c0ob00438c

DO - 10.1039/c0ob00438c

M3 - Journal article

VL - 9

SP - 1381

EP - 1388

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

ER -