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 < 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 < 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