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Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study
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SYSNO ASEP 0360998 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates. Synthesis, polymerase incorporation to DNA and electrochemical study Author(s) Macíčková-Cahová, Hana (UOCHB-X) RID, ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Horáková Brázdilová, Petra (BFU-R)
Havran, Luděk (BFU-R) RID, ORCID
Špaček, Jan (BFU-R) ORCID
Fojta, Miroslav (BFU-R) RID, ORCID
Hocek, Michal (UOCHB-X) RID, ORCIDNumber of authors 7 Source Title Chemistry - A European Journal. - : Wiley - ISSN 0947-6539
Roč. 17, č. 21 (2011), s. 5833-5841Number of pages 9 s. Language eng - English Country DE - Germany Keywords DNA polymerases ; electrochemistry ; nucleosides ; nucleotides ; organosulfur compounds Subject RIV CC - Organic Chemistry R&D Projects LC06035 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) LC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) GA203/09/0317 GA ČR - Czech Science Foundation (CSF) IAA400040901 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) CEZ AV0Z40550506 - UOCHB-X (2005-2011) AV0Z50040507 - BFU-R (2005-2011) AV0Z50040702 - BFU-R (2007-2013) UT WOS 000291594800011 DOI 10.1002/chem.201003496 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2012
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