Hydrogen-Bonding Interactions of 8-Substituted Purine Derivatives

0573771 - ÚOCHB 2024 RIV US eng J - Journal Article
Osifová, Zuzana - Šála, Michal - Dračínský, Martin
Hydrogen-Bonding Interactions of 8-Substituted Purine Derivatives.
ACS Omega. Roč. 8, č. 28 (2023), s. 25538-25548. ISSN 2470-1343. E-ISSN 2470-1343
R&D Projects: GA ČR(CZ) GA22-15374S
Institutional support: RVO:61388963
Keywords : oxidative DNA damage * computational analysis * electronic properties
OECD category: Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)
Impact factor: 4.1, year: 2022
Method of publishing: Open access
https://doi.org/10.1021/acsomega.3c03244

Hydrogen bonding between nucleobases is a crucial noncovalent interaction for life on Earth. Canonical nucleobases form base pairs according to two main geometries: Watson–Crick pairing, which enables the static functions of nucleic acids, such as the storing of genetic information, and Hoogsteen pairing, which facilitates the dynamic functions of these biomacromolecules. This precisely tuned system can be affected by oxidation or substitution of nucleobases, leading to changes in their hydrogen-bonding patterns. This paper presents an investigation into the intermolecular interactions of various 8-substituted purine derivatives with their hydrogen-bonding partners. The systems were analyzed using nuclear magnetic resonance spectroscopy and density functional theory calculations. Our results demonstrate that the stability of hydrogen-bonded complexes, or base pairs, depends primarily on the number of intermolecular H-bonds and their donor–acceptor alternation. No strong preferences for a particular geometry, either Watson–Crick or Hoogsteen, were found.
Permanent Link: https://hdl.handle.net/11104/0344133