Electrochemical reduction of azidophenyl-deoxynucleoside conjugates at mercury surface

Result code in 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>

Alternative codes found

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

Result on the web

<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>

Result language

angličtina

Original language name

Electrochemical reduction of azidophenyl-deoxynucleoside conjugates at mercury surface

Original language description

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.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2018

Confidentiality

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

Name of the periodical

Electrochimica Acta

ISSN

0013-4686

e-ISSN

—

Volume of the periodical

259

Issue of the periodical within the volume

January

Country of publishing house

GB - UNITED KINGDOM

Number of pages

9

Pages from-to

377-385

UT code for WoS article

000423968600042

EID of the result in the Scopus database

2-s2.0-85032949618