DNA base pairs: the effect of the aromatic ring on the strength of the Watson–Crick hydrogen bonding
The aromatic ring in DNA bases affects the Watson-Crick binding strength. Our quantum-chemical analyses, which compare the hydrogen bonding between the DNA bases and unsaturated analogs lacking the aromatic ring, reveal that this arises not from π-resonance assistance but from the electron-withdrawing (purines) or electron-donating (pyrimidines) effect of the heteroatom-containing ring on the frontier atoms. This electron redistribution modulates the electrostatics, steric Pauli repulsion, and σ-orbital interactions upon hydrogen bonding.
Authors
- Célia Fonseca Guerra (ORCID: https://orcid.org/0000-0002-2973-5321)
- M. WELL (ORCID: https://orcid.org/0000-0003-1778-5636)
- Celine Nieuwland (ORCID: https://orcid.org/0000-0002-5855-4386)
- L. Guillaumes
- Lodewijk V. Dekker (ORCID: https://orcid.org/0000-0001-5247-3297)
- Anna de Vey Mestdagh
- Cynthia Nieuweboer
Institutions
- Universitat de Girona (ES)
- Vrije Universiteit Amsterdam (NL)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00819k
- Citations
- 1
- Primary Topic
- DNA and Nucleic Acid Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.81
Funders
- Ministerio de Ciencia, Innovación y Universidades
- Generalitat de Catalunya
- Nederlandse Organisatie voor Wetenschappelijk Onderzoek