The Two Faces of the Guanyl Radical: Molecular Context and Behavior
The guanyl radical or neutral guanine radical G(-H)<sup>•</sup> results from the loss of a hydrogen atom (H<sup>•</sup>) or an electron/proton (e<sup>–</sup>/H<sup>+</sup>) couple from the guanine structures (G). The guanyl radical exists in two tautom...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/12/3511 |
| _version_ | 1797530837268299776 |
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| author | Chryssostomos Chatgilialoglu |
| author_facet | Chryssostomos Chatgilialoglu |
| author_sort | Chryssostomos Chatgilialoglu |
| collection | DOAJ |
| description | The guanyl radical or neutral guanine radical G(-H)<sup>•</sup> results from the loss of a hydrogen atom (H<sup>•</sup>) or an electron/proton (e<sup>–</sup>/H<sup>+</sup>) 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<sup>•+</sup> pair. The role of the two G(-H)<sup>•</sup> 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. |
| first_indexed | 2024-03-10T10:34:41Z |
| format | Article |
| id | doaj.art-efa7c5e5858f4016b6232e30a0044336 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T10:34:41Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-efa7c5e5858f4016b6232e30a00443362023-11-21T23:23:05ZengMDPI AGMolecules1420-30492021-06-012612351110.3390/molecules26123511The Two Faces of the Guanyl Radical: Molecular Context and BehaviorChryssostomos Chatgilialoglu0ISOF, Consiglio Nazionale delle Ricerche, 40129 Bologna, ItalyThe guanyl radical or neutral guanine radical G(-H)<sup>•</sup> results from the loss of a hydrogen atom (H<sup>•</sup>) or an electron/proton (e<sup>–</sup>/H<sup>+</sup>) 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<sup>•+</sup> pair. The role of the two G(-H)<sup>•</sup> 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.https://www.mdpi.com/1420-3049/26/12/3511guanineguanyl radicaltautomerismguanine radical cationoligonucleotidesDNA |
| spellingShingle | Chryssostomos Chatgilialoglu The Two Faces of the Guanyl Radical: Molecular Context and Behavior Molecules guanine guanyl radical tautomerism guanine radical cation oligonucleotides DNA |
| title | The Two Faces of the Guanyl Radical: Molecular Context and Behavior |
| title_full | The Two Faces of the Guanyl Radical: Molecular Context and Behavior |
| title_fullStr | The Two Faces of the Guanyl Radical: Molecular Context and Behavior |
| title_full_unstemmed | The Two Faces of the Guanyl Radical: Molecular Context and Behavior |
| title_short | The Two Faces of the Guanyl Radical: Molecular Context and Behavior |
| title_sort | two faces of the guanyl radical molecular context and behavior |
| topic | guanine guanyl radical tautomerism guanine radical cation oligonucleotides DNA |
| url | https://www.mdpi.com/1420-3049/26/12/3511 |
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