Benzoderivatives of nucleic acid bases as modified DNA building blocks.

TitleBenzoderivatives of nucleic acid bases as modified DNA building blocks.
Publication TypeJournal Article
Year of Publication2006
AuthorsHuertas, Oscar, Blas José Ramón, Soteras Ignacio, Orozco Modesto, and F Luque Javier
JournalJ Phys Chem A
Volume110
Pagination510-8
Date Published2006 Jan 19
ISSN1089-5639
KeywordsBenzene Derivatives, Gases, Hydrogen Bonding, Isomerism, Nucleic Acids, Purine Nucleosides, Pyrimidine Nucleosides, Solutions
Abstract

The tautomeric properties of benzoderivatives of the canonical nucleic acid bases have been studied by using different computational approaches. Attention has been paid to the impact of the benzene group in altering the tautomeric preferences of the canonical bases both in the gas phase and in aqueous solution. To this end, relative solvation free energies of the tautomers determined from Self-Consistent Reaction Field continuum calculations and Monte Carlo-Free Energy Perturbation are combined with gas-phase tautomerization free energies determined from quantum mechanical calculations. The results provide a detailed picture of the tautomeric preferences of the benzoderivatives of nucleic acid bases. This information is used to examine the recognition properties of the preferred tautomers of the benzo-fused derivatives, paying particular attention to the ability to form Watson-Crick hydrogen-bonding and stacking interactions as well as to the hydrophobic nature of the modified bases. The implications of present results on the potential use of benzo-fused bases as potential building blocks in modified DNA duplexes are examined.

DOI10.1021/jp052126u