About: Tetrathiafulvalene-Labelled Nucleosides and Nucleoside Triphosphates: Synthesis, Electrochemistry and the Scope of Their Polymerase Incorporation into DNA     Goto   Sponge   NotDistinct   Permalink

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  • The title 5-substituted pyrimidines (U and C) and 7-substituted 7-deazapurines (7-deazaA and 7-deazaG) bearing tetrathiafulvelene (TTF) attached through an acetylene linker have been prepared by cross-coupling of the corresponding 5- or 7-iodo derivatives of nucleosides with 2-ethynyltetrathiafulvalene. Their subsequent triphosphorylation gave the corresponding nucleoside triphosphates (dNTPs). Square-wave voltammetry of the TTF-labelled nucleosides and nucleotides showed two peaks, which correspond to two reversible one-electron redox processes in the TTF moiety. Polymerase incorporation of the TTF-labelled dNTPs into DNA has also been studied. Multiple incorporations were rather problematic and only by using dCTTFTP was efficient primer extension observed with Vent (exo-)polymerase. Single nucleotide extension was successful with labelled A (dA*TTFTP) and C (dCTTFTP) nucleotides. Inhibition of the polymerase was observed at higher concentrations of dNTTFTPs.
  • The title 5-substituted pyrimidines (U and C) and 7-substituted 7-deazapurines (7-deazaA and 7-deazaG) bearing tetrathiafulvelene (TTF) attached through an acetylene linker have been prepared by cross-coupling of the corresponding 5- or 7-iodo derivatives of nucleosides with 2-ethynyltetrathiafulvalene. Their subsequent triphosphorylation gave the corresponding nucleoside triphosphates (dNTPs). Square-wave voltammetry of the TTF-labelled nucleosides and nucleotides showed two peaks, which correspond to two reversible one-electron redox processes in the TTF moiety. Polymerase incorporation of the TTF-labelled dNTPs into DNA has also been studied. Multiple incorporations were rather problematic and only by using dCTTFTP was efficient primer extension observed with Vent (exo-)polymerase. Single nucleotide extension was successful with labelled A (dA*TTFTP) and C (dCTTFTP) nucleotides. Inhibition of the polymerase was observed at higher concentrations of dNTTFTPs. (en)
Title
  • Tetrathiafulvalene-Labelled Nucleosides and Nucleoside Triphosphates: Synthesis, Electrochemistry and the Scope of Their Polymerase Incorporation into DNA
  • Tetrathiafulvalene-Labelled Nucleosides and Nucleoside Triphosphates: Synthesis, Electrochemistry and the Scope of Their Polymerase Incorporation into DNA (en)
skos:prefLabel
  • Tetrathiafulvalene-Labelled Nucleosides and Nucleoside Triphosphates: Synthesis, Electrochemistry and the Scope of Their Polymerase Incorporation into DNA
  • Tetrathiafulvalene-Labelled Nucleosides and Nucleoside Triphosphates: Synthesis, Electrochemistry and the Scope of Their Polymerase Incorporation into DNA (en)
skos:notation
  • RIV/00216275:25310/09:00009576!RIV10-MSM-25310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(LC06035)
http://linked.open...iv/cisloPeriodika
  • 21
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 346099
http://linked.open...ai/riv/idVysledku
  • RIV/00216275:25310/09:00009576
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • nucleosides; nucleotides; nucleic acids; cross-coupling; DNA polymerase; tetrathiafulvalene (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [C8F5754B691C]
http://linked.open...i/riv/nazevZdroje
  • European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 2009
http://linked.open...iv/tvurceVysledku
  • Fojta, Miroslav
  • Havran, Luděk
  • Hocek, Michal
  • Horáková, Petra
  • Pohl, Radek
  • Riedl, Jan
  • Šebest, Peter
issn
  • 1434-193X
number of pages
http://localhost/t...ganizacniJednotka
  • 25310
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