Benzoquinone and naphthoquinone based redox-active labels for electrochemical detection of modified oligonucleotides on Au electrodes. Issue 3 (20th January 2016)

• Record Type: Journal Article
• Authors: Shundrin, Leonid A.; Irtegova, Irina G.; Vasilieva, Nadezhda V.; Khalfina, Irina A.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 3(2016)
• Page Start: 392
• Page End: 395
• Publication Date: 2016-01-20
• Subjects: Quinones -- Redox-active labels -- Electrochemical reduction -- Cyclic voltammetry -- Modified oligonucleotides; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.12.035
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The reaction of 1, 4-benzoquinone and 1, 4-naphthoquinone with β-thiopropionic acid yielded 3-[(3, 6-dioxocyclohexa-1, 4-diene-1-yl)thio]propionic and 3-[(1, 4-dioxo-1, 4-dihydronaphthalene-2-yl)thio]propionic acids, respectively. These compounds were used to modify oligonucleotides to allow their electrochemical detection on the surface of Au electrodes using cyclic voltammetry. Electrochemical reduction of the corresponding amides, modeling the bonding of the redox-active labels with molecules that are not electrochemically active, was also studied.