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Citation: HOU Ruo-Bing, LI Wei-Wei, SHEN Xing-Can. Ring-Opening Reaction Mechanism of 8-Hydroxyguanine Radical[J]. Acta Physico-Chimica Sinica, ;2008, 24(02): 269-274. doi: 10.3866/PKU.WHXB20080215 shu

Ring-Opening Reaction Mechanism of 8-Hydroxyguanine Radical

1.
School of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, Guangxi Province, P. R. China

Received Date: 7 August 2007
Available Online: 13 December 2007

The theoretical studies on the mechanisms of ring-opening reaction of 8-hydroxyguanine radical were performed by the experimentally calibrated theoretical method of B3LYP/DZP++. All of the computational results revealed that the ring-opening reaction occured through a pathway including two elementary reactions, the C8—N9 bond-broken step followed by a transfer step of cation-like hydrogen atom of the hydroxyl moiety. The high activation energy in the transfer reaction of hydrogen atom in the absence of water led this reaction to be somewhat difficult; on the contrary, the hydrogen transfer might occur feasibly with assistance of one water molecule due to the formation of a six-member ring transition state which was beneficial to lower the reaction activation energy. The difference of the activation energies of two elementary reactions demonstrated that the rate-limiting steps of ring-opening reaction in the absence of water and in the presence of water were the hydrogen transfer step and C8—N9 bond-broken process, respectively.
- 8-Hydroxyguanine radical; Ring-opening reaction; H-transfer reaction; Catalytic action of water
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