Adenine Tautomers: Relative Stabilities, Ionization Energies, and Mismatch with Cytosine

Fonseca Guerra, C.; Bickelhaupt, F. M.; Saha, S.; Wang, F.

doi:10.1021/jp057275r

Cited by 127Advanced Chemical Physics StudiesDNA and Nucleic Acid ChemistryChemical Reaction Mechanisms

Adenine Tautomers: Relative Stabilities, Ionization Energies, and Mismatch with Cytosine

Fonseca Guerra, C., Bickelhaupt, F. M., Saha, S., Wang, F.·2006·The Journal of Physical Chemistry A

DOI 10.1021/jp057275r

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Abstract

In this study, we have investigated 12 tautomers of the DNA base adenine at the BP86/TZ2P and BP86/QZ4P levels of density functional theory. The vertical and adiabatic ionization energies of all tautomers were determined as the difference in energy between the radical cation and the corresponding neutral system. Furthermore, an evaluation is made for the eigenvalue spectra calculated with the SAOP functional, which is shown to lead to substantial improvements for orbital energies compared to BP86. We have also explored the correlations between the Kohn-Sham orbitals of the different tautomers at the BP86/QZ4P and SAOP/QZ4P levels. Finally, we discuss implications of the existence of the tautomeric forms of adenine for the DNA replication.

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T2C/A2G transitions are known in biology and are the result of a tautomeric shift of adenine, from its amine to its imine form.
“T2C/A2G transitions are known in biology and are the result of a tautomeric shift of adenine, from its amine to its imine form.[32]”
From Integrating DNA Encapsulates and Digital Microfluidics for Automated Data Storage in DNA (2022) · cites this paper as [32]

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Authors: Fonseca Guerra, C., Bickelhaupt, F. M., Saha, S., & Wang, F.
Affiliations: Theoretische Chemie, Scheikundig Laboratorium der Vrije Universiteit, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands, and Centre for Molecular Simulation, Swinburne University of Technology, P.O. Box 218, Hawthorn, Melbourne, Victoria, 3122, Australia
Swinburne University of Technology (AU)
ORCID: Bickelhaupt, F. M.
Saha, S.
Wang, F.
Venue: The Journal of Physical Chemistry A
Publisher: American Chemical Society (ACS)
Published: 2006-03-01
Volume: 110
Issue: 11
Pages: 4012-4020
ISSN: 1089-5639 (ISSN-L)
1520-5215
DOI: 10.1021/jp057275r
OpenAlex: W2002191658
Cited by: 127
References: 62
Citations by year: 2025: 3 · 2024: 2 · 2023: 2 · 2022: 5 · 2021: 3 · 2020: 5 · 2019: 3 · 2018: 4 · 2017: 5 · 2016: 4 · 2015: 10 · 2014: 13 · 2013: 13 · 2012: 12
FWCI: 6.00
Type: journal article
Language: en
Open access: closed
Locations: The Journal of Physical Chemistry A (publishedVersion)
PubMed (publishedVersion)
VU Research Portal (publishedVersion)
Digital Academic REpository of VU University Amsterdam (Vrije Universiteit Amsterdam) (submittedVersion)
Swinburne figshare (Swinburne University of Technology) (submittedVersion)
Data Archiving and Networked Services (DANS) (submittedVersion)
Funders: Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Topics: Physical Sciences › Physics and Astronomy › Atomic and Molecular Physics, and Optics › Advanced Chemical Physics Studies
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
Keywords: ionization potential, tautomer relative stability, Kohn-Sham orbitals, BP86 functional, radical cations, DNA replication
MeSH terms: Adenine, Cytosine, Isomerism, Models, Chemical, Models, Molecular, Molecular Structure

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Adenine Tautomers: Relative Stabilities, Ionization Energies, and Mismatch with Cytosine

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