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Prototropic changes in cationic base‐pair adducts. I. Guanine protonation
Author(s) -
Ford George P.,
Wang Bingze
Publication year - 1992
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560440415
Subject(s) - protonation , guanine , chemistry , cytosine , adduct , proton , cationic polymerization , base (topology) , base pair , nucleobase , stereochemistry , nucleic acid , ring (chemistry) , photochemistry , dna , nucleotide , organic chemistry , biochemistry , ion , physics , mathematical analysis , mathematics , quantum mechanics , gene
Abstract AM 1 calculations have been used to study the effects of protonation on the structures, energies, and, in some cases, proton transfer reactions of guanine cytosine base pairs. Protonation at the guanine O 6 ‐position, or at various ring sites, leads to a relatively facile conversion to a surprisingly stable complementary base pairs following proton transfer to the cytosine 3‐position. In the case of O 6 ‐protonation, this constitutes a direct route to guanine enolization. It is suggested that the spontaneous formation of apyrimidinic sites in nucleic acids take place via prior protonation of guanine moieties in the opposite strand. © 1992 John Wiley & Sons, Inc.