Reaction mechanism of the cation radicals of thymine and thymine derivatives in aqueous solution: A theoretical study

Author:

Wu Lidan1ORCID,Meng Xiaoyan1,Wang Xuejun1,Yu Leshu1,Peng Siyan1,Xie Jianying1

Affiliation:

1. School of Chemistry and Environmental Science, Shangrao Normal University, Shangrao Jiangxi 334001, P. R. China

Abstract

Mechanisms of decomposition reaction of thymine cation radicals (T[Formula: see text]), 1-methyl substituted T[Formula: see text] (1-MeT[Formula: see text]), and 1,3-dimethyl substituted T[Formula: see text] (1,3-Me2T[Formula: see text]) generated by ionizing radiation or one-electron oxidation to thymine, 1-methylthymine and 1,3-dimethylthymine in aqueous solution have been investigated by theoretical calculations. Seven reaction paths including H2O or OH[Formula: see text] addition, and deprotonation were considered. The most likely reaction for T[Formula: see text] decomposition is N1 deprotonation forming T(-N1H)[Formula: see text]. When N1 hydrogen is replaced by methyl, T[Formula: see text] would deprotonate from C5 methyl group generating 1-methyl substituted UCH[Formula: see text] in neutral solution, and reaction with OH[Formula: see text] producing 1-methyl substituted T6OH[Formula: see text] in basic solution. When N1 and N3 hydrogens are both replaced by methyl, T[Formula: see text] decomposition reaction is similar to 1-MeT[Formula: see text], indicating that N3 hydrogen barely influences the subsequent reaction of 1-MeT[Formula: see text]. These results can provide theoretical support for experimental observations.

Funder

Science and Technology Research Project in Jiangxi Province Department of Education

National Natural Science Foundation of China

Natural Science Key Project of Jiangxi Province

Publisher

World Scientific Pub Co Pte Lt

Subject

Computational Theory and Mathematics,Physical and Theoretical Chemistry,Computer Science Applications

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