Počet záznamů: 1  

Aqueous Heck Cross-Coupling Preparation of Acrylate-Modified Nucleotides and Nucleoside Triphosphates for Polymerase Synthesis of Acrylate-Labeled DNA

  1. 1.
    0420905 - ÚOCHB 2014 RIV US eng J - Článek v odborném periodiku
    Daďová, Jitka - Vidláková, Pavlína - Pohl, Radek - Havran, Luděk - Fojta, Miroslav - Hocek, Michal
    Aqueous Heck Cross-Coupling Preparation of Acrylate-Modified Nucleotides and Nucleoside Triphosphates for Polymerase Synthesis of Acrylate-Labeled DNA.
    Journal of Organic Chemistry. Roč. 78, č. 19 (2013), s. 9627-9637. ISSN 0022-3263
    Grant CEP: GA AV ČR(CZ) IAA400040901
    Institucionální podpora: RVO:61388963 ; RVO:68081707
    Klíčová slova: nucleic-acids * enzymatic incorporation * protein interactions * functionalized DNA
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 4.638, rok: 2013

    Aqueous-phase Heck coupling methodology was developed for direct attachment of butyl acrylate to 5-iodoracil, 5-iodocytosine, 7-iodo-7-deazaadenine, and 7-iodo-7-deazaguanine 2'-deoxyribonncleoside 5'-O-monophosphates (dNMPs). and 5'-O-triphosphates (dNTPs) and compared with the classical approach of phosphorylation of the corresponding modified nucleosides. The 7-substituted 7-deazapurine nucleotides (dA(BA)MP, dA(BA)TP, dG(BA)MP, and dG(BA)TP) were prepared by the direct Heck coupling of nucleotides in good yields (35-55%), whereas the pyrimidine nucleotides reacted. poorly and the corresponding BA-Modified dNTPs were prepared by triphosphorylation of the Modified nucleosides. The. acrylate-modified dN(BA)TPs (N = A, C, and U) were good substrates for DNA polymerases and were used for enzymatic synthesis of acrylate-modified DNA by primer extension, whereas dG(BA)TP was an inhibitor of polymerases. The butyl acrylate group was found to be a useful redox label giving a strong reduction peak at -1.3 to -1.4 V in cyclic voltammetry.
    Trvalý link: http://hdl.handle.net/11104/0227453