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Electrochemical reduction of azidophenyl-deoxynucleoside conjugates at mercury surface

Identifikátory výsledku

  • Kód výsledku v IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10374845" target="_blank" >RIV/00216208:11310/18:10374845 - isvavai.cz</a>

  • Nalezeny alternativní kódy

    RIV/68081707:_____/18:00500228 RIV/61388963:_____/18:00500228 RIV/00216224:14740/18:00101394

  • Výsledek na webu

    <a href="https://doi.org/10.1016/j.electacta.2017.10.128" target="_blank" >https://doi.org/10.1016/j.electacta.2017.10.128</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1016/j.electacta.2017.10.128" target="_blank" >10.1016/j.electacta.2017.10.128</a>

Alternativní jazyky

  • Jazyk výsledku

    angličtina

  • Název v původním jazyce

    Electrochemical reduction of azidophenyl-deoxynucleoside conjugates at mercury surface

  • Popis výsledku v původním jazyce

    Azidophenyl-linked nucleotides were previously used for redox-labelling of DNA. Lack of information about electrochemical behavior of aromatic azides in aqueous media and more complex reduction mechanism from to-date presented straightforward two electron reduction to corresponding amines and diatomic nitrogen led us to study the electrochemical reduction process more in detail. Model potassium 4-azidophenyltrifluoroborate (AzPTFB) and the corresponding AzP-linked nucleosides, 7-(4-azidophenyl)-7-deaza-20-deoxyadenosine (dAAzP) and 5-(4-azidophenyl)-20-deoxycytidine (dCAzP), were studied using DC and AC polarography, cyclic voltammetry and electrochemical impedance spectroscopy at dropping mercury electrode or at hanging mercury drop electrode in aqueous buffers. Electrochemical reduction of the azidophenyl conjugates is influenced by pH. Even if electrolysis of AzPTFB and dAAzP at mercury pool confirmed consumption of two electrons per molecule, simple two electron reduction of azide group to amine proceed only in acid electrolytes (pH &lt; 2). Preparative chromatography of the solution obtained after dAAzP electrolysis in ammonium formate-phosphate buffer pH 6.9 and potassium chloride-phosphate buffer pH 6.9 revealed also presence of formylaminophenyl- and phenyl-derivatives. Nevertheless, intermediates such as dimers of the amine compounds and/or hydroxylamine-derivatives, which yield characteristic anodic peak in CV, are transiently formed. The intermediates are finally transformed to amines via reduction at more negative potentials. According to the results, mechanism of dAAzp electrochemical reduction is proposed in this work.

  • Název v anglickém jazyce

    Electrochemical reduction of azidophenyl-deoxynucleoside conjugates at mercury surface

  • Popis výsledku anglicky

    Azidophenyl-linked nucleotides were previously used for redox-labelling of DNA. Lack of information about electrochemical behavior of aromatic azides in aqueous media and more complex reduction mechanism from to-date presented straightforward two electron reduction to corresponding amines and diatomic nitrogen led us to study the electrochemical reduction process more in detail. Model potassium 4-azidophenyltrifluoroborate (AzPTFB) and the corresponding AzP-linked nucleosides, 7-(4-azidophenyl)-7-deaza-20-deoxyadenosine (dAAzP) and 5-(4-azidophenyl)-20-deoxycytidine (dCAzP), were studied using DC and AC polarography, cyclic voltammetry and electrochemical impedance spectroscopy at dropping mercury electrode or at hanging mercury drop electrode in aqueous buffers. Electrochemical reduction of the azidophenyl conjugates is influenced by pH. Even if electrolysis of AzPTFB and dAAzP at mercury pool confirmed consumption of two electrons per molecule, simple two electron reduction of azide group to amine proceed only in acid electrolytes (pH &lt; 2). Preparative chromatography of the solution obtained after dAAzP electrolysis in ammonium formate-phosphate buffer pH 6.9 and potassium chloride-phosphate buffer pH 6.9 revealed also presence of formylaminophenyl- and phenyl-derivatives. Nevertheless, intermediates such as dimers of the amine compounds and/or hydroxylamine-derivatives, which yield characteristic anodic peak in CV, are transiently formed. The intermediates are finally transformed to amines via reduction at more negative potentials. According to the results, mechanism of dAAzp electrochemical reduction is proposed in this work.

Klasifikace

  • Druh

    J<sub>imp</sub> - Článek v periodiku v databázi Web of Science

  • CEP obor

  • OECD FORD obor

    10401 - Organic chemistry

Návaznosti výsledku

  • 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)

Ostatní

  • Rok uplatnění

    2018

  • Kód důvěrnosti údajů

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

Údaje specifické pro druh výsledku

  • Název periodika

    Electrochimica Acta

  • ISSN

    0013-4686

  • e-ISSN

  • Svazek periodika

    259

  • Číslo periodika v rámci svazku

    January

  • Stát vydavatele periodika

    GB - Spojené království Velké Británie a Severního Irska

  • Počet stran výsledku

    9

  • Strana od-do

    377-385

  • Kód UT WoS článku

    000423968600042

  • EID výsledku v databázi Scopus

    2-s2.0-85032949618