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The Two Faces of the Guanyl Radical: Molecular Context and Behavior

1
ISOF, Consiglio Nazionale delle Ricerche, 40129 Bologna, Italy
2
Center of Advanced Technologies, Adam Mickiewicz University, 61-712 Poznań, Poland
Academic Editor: Nicola Borbone
Molecules 2021, 26(12), 3511; https://doi.org/10.3390/molecules26123511
Received: 6 April 2021 / Revised: 29 May 2021 / Accepted: 1 June 2021 / Published: 9 June 2021
(This article belongs to the Special Issue Biomimetic Radical Chemistry and Applications 2021)
The guanyl radical or neutral guanine radical G(-H) results from the loss of a hydrogen atom (H) or an electron/proton (e/H+) couple from the guanine structures (G). The guanyl radical exists in two tautomeric forms. As the modes of formation of the two tautomers, their relationship and reactivity at the nucleoside level are subjects of intense research and are discussed in a holistic manner, including time-resolved spectroscopies, product studies, and relevant theoretical calculations. Particular attention is given to the one-electron oxidation of the GC pair and the complex mechanism of the deprotonation vs. hydration step of GC•+ pair. The role of the two G(-H) tautomers in single- and double-stranded oligonucleotides and the G-quadruplex, the supramolecular arrangement that attracts interest for its biological consequences, are considered. The importance of biomarkers of guanine DNA damage is also addressed. View Full-Text
Keywords: guanine; guanyl radical; tautomerism; guanine radical cation; oligonucleotides; DNA; G-quadruplex; time-resolved spectroscopies; reactive oxygen species (ROS); oxidation guanine; guanyl radical; tautomerism; guanine radical cation; oligonucleotides; DNA; G-quadruplex; time-resolved spectroscopies; reactive oxygen species (ROS); oxidation
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MDPI and ACS Style

Chatgilialoglu, C. The Two Faces of the Guanyl Radical: Molecular Context and Behavior. Molecules 2021, 26, 3511. https://doi.org/10.3390/molecules26123511

AMA Style

Chatgilialoglu C. The Two Faces of the Guanyl Radical: Molecular Context and Behavior. Molecules. 2021; 26(12):3511. https://doi.org/10.3390/molecules26123511

Chicago/Turabian Style

Chatgilialoglu, Chryssostomos. 2021. "The Two Faces of the Guanyl Radical: Molecular Context and Behavior" Molecules 26, no. 12: 3511. https://doi.org/10.3390/molecules26123511

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