Abstract
The water-assisted hydrolytic deamination mechanism of adenine was studied using density functional method at B3LYP/6-311G(d,p) level. Intrinsic reaction coordinate (IRC) calculations were performed on the transition states to verify whether it is the real transition states that connect the corresponding intermediates. Single-point calculations were carried out on the previous optimized geometries obtained during IRC calculations. The activation energies have also been calculated using G3MP2//B3LYP/6-311G(d,p) method. The water molecules attack the adenine and a tetrahedral intermediate forms. Then, two different intermediates have been obtained through different bond rotations. In pathway a, the second water molecule takes part in the formation of transition state and acts as a bridge to transfer hydrogen atom, while in pathway b, the second water molecule does not involve in the creation of transition state and only acts as a medium. The energy barriers are 23.40 and 37.17 kcal/mol for pathways a and b, respectively.
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Acknowledgments
This work was supported by the basic research sustentation fund of cosmetics in vitro toxicology study from Chinese Academy of Inspection and Quarantine (No. 2007JK017) and Ph.D. foundation of Shandong Province (No. 2008BS02014).
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Zheng, H., Meng, F. Theoretical study of water-assisted hydrolytic deamination mechanism of adenine. Struct Chem 20, 943–949 (2009). https://doi.org/10.1007/s11224-009-9495-z
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DOI: https://doi.org/10.1007/s11224-009-9495-z