Journal of Molecular Modeling

, Volume 19, Issue 9, pp 3543–3549 | Cite as

Theoretical study of the pre- and post-translational effects of adenine and thymine tautomers and methyl derivatives

  • Noel Gardner
  • David Magers
  • Glake HillJr.
Original Paper


The study of pre-translational effects (ionization, tautomerization) and post-translational effects (methylation) of adenine and thymine has only recently been the focus of some studies. These effects can potentially help regulate gene expression as well as potentially disrupt normal gene function. Because of this wide array of roles, greater insight into these effects in deoxyribonucleic acids (DNA) are paramount. There has been considerable research of each phenomenon (tautomerization, methylation and ionization) individually. In this work, we attempt to shed light upon the pre-translational effects and post translational effects of adenine and thymine by investigating the electron affinities (EAs) and ionization potentials (IPs) of the major and minor tautomers and their methyl derivatives. We performed all calculations using the density functional theory (DFT) B3LYP functional accompanied with 6-311G(d,p), 6-311+G(d,p) and 6-311++G(df,pd) basis sets. Our results reveal that the thymine tautomer has a higher EA and IP than the adenine tautomers. The higher EA suggests that an electron that attaches to the AT base pair would predominately attach to the thymine instead of adenine. The higher IP would suggest that an electron that is removed from the AT base pair would be predominately removed from the adenine within the base pair. Understanding how tautomerization, ionization and methylation differences change effects, discourages, or promotes one another is lacking. In this work, we begin the steps of integrating these effects with one another, to gain a greater understanding of molecular changes in DNA bases.


Electron affinity and ionization potential Methylation Pre-translational and post-translational effects Tautomerization 



I would like to acknowledge Dr. Kari Copeland for her expertise. This work is supported in part by United States Department of Education Title III Graduate Education Program at Jackson State University, Grant No. P031B090210-12, the National Science Foundation, Experimental Program to Stimulate Competitive Research (EPSCoR), Experimental Program to Stimulate (EPS) 0903787 and EPS 1006883, and Mississippi Center for Supercomputing Research (computer time).


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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  1. 1.Jackson State UniversityJacksonUSA
  2. 2.Mississippi CollegeClintonUSA

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