Abstract
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.
Highlights
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 free radical chemistry associated with guanine (Gua) and its derivatives, guanosine (Guo), 2’-deoxyguanosine, guanosine-50 -monophosphate (GMP), and 20 deoxyguanosine-50 -monophosphate, is of particular interest due to its biological relevance
Upon formation of G+, fast deprotonation occurs by the loss of a proton to give the guanyl radical G(-H), named the guanine radical or neutral guanine radical
Summary
The free radical chemistry associated with guanine (Gua) and its derivatives, guanosine (Guo), 2’-deoxyguanosine (dGuo), guanosine-50 -monophosphate (GMP), and 20 deoxyguanosine-50 -monophosphate (dGMP), is of particular interest due to its biological relevance. The main objective of this review is to summarize the behavior of G(-H) in nucleosides and nucleotides and give an overview of its formation in a macromolecular environment, such as single-stranded (ss), double-stranded (ds) ODNs, and G-quadruplex arrangements
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