Electrochemical reduction and oxidation of eight unnatural 2′-deoxynucleosides at a pyrolytic graphite electrode

• Published in: Electrochimica acta Vol. 362; p. 137210
• Main Authors: Špaček, Jan, Karalkar, Nilesh, Fojta, Miroslav, Wang, Joseph, Benner, Steven A.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.12.2020; Elsevier BV
• Subjects: Chemical reduction; Deoxyribonucleic acid; DNA; Electrochemical analysis; Electrochemical oxidation; Electrochemical reduction; Electrochemistry; Electrodes; Oxidation; Pyrolytic graphite; Unnatural DNA; Electrochemistry; Pyrolytic graphite; Electrochemical reduction; Electrochemical oxidation; Unnatural DNA
• ISSN: 0013-4686; 1873-3859
• DOI: 10.1016/j.electacta.2020.137210

•Electroanalysis of Artificially Expanded Genetic Information System (AEGIS).•Electroactivity of 8 AEGIS 2’-deoxynucleosides was described of which 1 was inactive.•Pyrolytic graphite electrode was used for reductions at highly negative potentials.•Pyrolytic graphite electrode was used for oxidations at highly positive potentials.•Newly described peaks will be later used for AEGIS base identification in DNA. Recently we showed the reduction and oxidation of six natural 2′-deoxynucleosides in the presence of the ambient oxygen using the very broad potential window of a pyrolytic graphite electrode (PGE). Using the same procedure, 2′-deoxynucleoside analogs (dNs) that are parts of an artificially expanded genetic information system (AEGIS) were analyzed. Seven of the eight tested AEGIS dNs provided specific signals (voltammetric redox peaks). These signals, described here for the first time, will be used in future work to analyze DNA built from expanded genetic alphabets, helping to further develop AEGIS technology and its applications. Comparison of the electrochemical behavior of unnatural dNs with the previously documented behaviors of natural dNs also provides insights into the mechanisms of their respective redox processes.