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Mechanistic clues to the mutagenicity of alkylated DNA bases: A theoretical study
Gerard S. Davies
Published in
1989
PMID: 2559256
Volume: 140
   
Issue: 3
Pages: 345 - 354
Abstract
Experiment indicates that the N7-guanine site in DNA is not "promutagenic" (mutation-inducing) on alkylation, while the O6-guanine and O4-thymine sites are so. These differences in nucleic acid template activity are attributed to corresponding differences in acidity of the Watson-Crick hydrogen bonding protons. Mechanistic indicators for ease of Watson-Crick proton loss are calculated using molecular orbital theory for DNA bases alkylated at the N7-guanine, O6-guanine and O4-thymine sites. Their values point to a definite favouring of the proton loss for the O-alkylated bases compared to the N7-alkylguanines. This may suggest the possibility that, at biological pH, the O-alkylated bases deprotonate readily while the N7-alkylguanines do not, thus accounting for observed differences in promutagenicity and nucleic acid template activity. © 1989 Academic Press Limited.
About the journal
JournalJournal of Theoretical Biology
ISSN00225193
Open AccessNo
Concepts (11)
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    Dna base
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    Alkylation
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    Mutagenicity
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    Theoretical study
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    DNA
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    Electrons
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    Hydrogen bonding
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    Mutation
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    Protons
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    PURINE NUCLEOTIDES
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    PYRIMIDINE NUCLEOTIDES