Počet záznamů: 1

Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study

  1. 1.
    0360998 - UOCHB-X 2012 RIV DE eng J - Článek v odborném periodiku
    Macíčková-Cahová, Hana - Pohl, Radek - Horáková Brázdilová, Petra - Havran, Luděk - Špaček, Jan - Fojta, Miroslav - Hocek, Michal
    Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study.
    Chemistry - A European Journal. Roč. 17, č. 21 (2011), s. 5833-5841 ISSN 0947-6539
    Grant CEP: GA MŠk(CZ) LC06035; GA MŠk LC512; GA ČR GA203/09/0317; GA AV ČR(CZ) IAA400040901
    Výzkumný záměr: CEZ:AV0Z40550506; CEZ:AV0Z50040507; CEZ:AV0Z50040702
    Klíčová slova: DNA polymerases * electrochemistry * nucleosides * nucleotides * organosulfur compounds
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 5.925, rok: 2011

    Aqueous Suzuki-Miyaura cross-coupling reactions of halogenated nucleosides, nucleotides and nucleoside triphosphates (dNTPs) derived from 5-iodocytosine and 7-iodo-7-deazaadenine with methyl-, benzyl- and tritylsufanylphenylboronic acids gave the corresponding alkylsulfanylphenyl derivatives of nucleosides and nucleotides. The modified dNTPs were incorporated to DNA by primer extension using Vent(exo-) polymerase. Electrochemical behaviour of the alkyl-sulfanylphenyl nucleosides indicated formation of compact layers on the electrode. Modified nucleotides and DNA bearing benzyl- or tritylsulfanylphenyl moieties produced signals in [Co(NH3)6]3+ ammonium buffer attributable to the Brdicka catalytic reponses (BCR), depending on negative potential applied. Repeated potential scans in this medium of constant current chronopotentiometric showed increased BCR suggesting the deprotection of the alkylsulfanyl derivatives to free thiols under those conditions.
    Trvalý link: http://hdl.handle.net/11104/0198420