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

Resumé

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.
OriginalsprogEngelsk
TidsskriftOrganic & Biomolecular Chemistry
Vol/bind9
Sider (fra-til)1381 - 1388
Antal sider8
ISSN1477-0520
DOI
StatusUdgivet - 2011

Citer dette

Jørgensen, Anna Søndergaard ; Shaikh, Khalil Isak ; Enderlin, Gerald ; Ivarsen, Elise ; Kumar, Surender ; Nielsen, Poul. / The synthesis of double-headed nucleosides by the CuAAC reaction and their effect in secondary nucleic acid structures. I: Organic & Biomolecular Chemistry. 2011 ; Bind 9. s. 1381 - 1388.
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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 tidsskriftTidsskriftartikelForskningpeer 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

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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

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SP - 1381

EP - 1388

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

ER -