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

0360998 - ÚOCHB 2012 RIV DE eng J - Journal Article
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. E-ISSN 1521-3765
R&D Projects: GA MŠMT(CZ) LC06035; GA MŠMT LC512; GA ČR GA203/09/0317; GA AV ČR(CZ) IAA400040901
Institutional research plan: CEZ:AV0Z40550506; CEZ:AV0Z50040507; CEZ:AV0Z50040702
Keywords : DNA polymerases * electrochemistry * nucleosides * nucleotides * organosulfur compounds
Subject RIV: CC - Organic Chemistry
Impact factor: 5.925, year: 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.
Permanent Link: http://hdl.handle.net/11104/0198420