Theoretical studies on the intermolecular interactions of potentially primordial base-pair analogues

Judit E. Šponer, Álvaro Vázquez-Mayagoitia, Bobby G. Sumpter, Jerzy Leszczynski, Jiří Šponer, Michal Otyepka, Pavel Banáš, Miguel Fuentes-Cabrera

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Recent experimental studies on the Watson-Crick type base pairing of triazine and aminopyrimidine derivatives suggest that acid/base properties of the constituent bases might be related to the duplex stabilities measured in solution. Herein we use high-level quantum chemical calculations and molecular dynamics simulations to evaluate the base pairing and stacking interactions of seven selected base pairs, which are common in that they are stabilized by two N-H⋯O hydrogen bonds separated by one N-H⋯N hydrogen bond. We show that neither the base pairing nor the base stacking interaction energies correlate with the reported pKa data of the bases and the melting points of the duplexes. This suggests that the experimentally observed correlation between the melting point data of the duplexes and the pKa values of the constituent bases is not rooted in the intrinsic base pairing and stacking properties. The physical chemistry origin of the observed experimental correlation thus remains unexplained and requires further investigations. In addition, since our calculations are carried out with extrapolation to the complete basis set of atomic orbitais and with inclusion of higher electron correlation effects, they provide reference data for stacking and base pairing energies of non-natural bases.

Original languageEnglish
Pages (from-to)3057-3065
Number of pages9
JournalChemistry - A European Journal
Volume16
Issue number10
DOIs
StatePublished - Mar 8 2010

Keywords

  • Ab initio calculations
  • Base pairing
  • Molecular dynamics
  • Origin of life
  • Prebiotic chemistry

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