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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F11%3A00360998" target="_blank" >RIV/61388963:_____/11:00360998 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/68081707:_____/11:00360998

Výsledek na webu

<a href="http://dx.doi.org/10.1002/chem.201003496" target="_blank" >http://dx.doi.org/10.1002/chem.201003496</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.201003496" target="_blank" >10.1002/chem.201003496</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2011

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

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Svazek periodika

17

Číslo periodika v rámci svazku

21

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

5833-5841

Kód UT WoS článku

000291594800011

EID výsledku v databázi Scopus

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