Citation: LIU Hai-Ying, MENG Fan-Cui, LI Ping, DING Shi-Liang. Effects of CH₃OH and NH₃ on the Hydrolytic Deamination Mechanismof Adenine[J]. Acta Physico-Chimica Sinica, ;2010, 26(11): 3067-3072. doi: 10.3866/PKU.WHXB20101106 shu

Effects of CH₃OH and NH₃ on the Hydrolytic Deamination Mechanismof Adenine

1.
1. School of Science, University of Jinan, Jinan 250022, P. R. China;
2Tianjin Institute of Pharmaceutical Research, Tianjin 300193, P. R. China;
3School of Physics, Shandong University, Jinan 250100, P. R. China

Received Date: 27 April 2010
Available Online: 13 September 2010
Fund Project: 山东省博士基金(2008BS02014) (2008BS02014)济南大学校基金(XKY0809)资助项目 (XKY0809)

The effects of CH₃OH and NH₃ on the hydrolytic deamination mechanism of adenine were studied by density functional theory at the B3LYP/6-311G(d,p) level. The results reveal that a tetrahedral intermediate is formed after a nucleophilic attack by a water molecule. Two intermediates are formed through conformational changes and different pathways are responsible. In pathway a, an assistant molecule takes part in the formation of the transition state and acts as a bridge to transfer a hydrogen atom, while in pathway b the assistant molecule is not involved in the creation of the transition state and acts only as a medium. The adenine takes place an amine-imine tautomerization before the nucleophilic attack under NH₃, which is not the case for the methanol-assisted mechanism. Energy results indicate that the energy barrier of the methanol-assisted adenine deamination is similar to that of the water-assisted reaction while the ammonia-assisted reaction has amuch higher energy barrier compared with the water-assisted reaction.
- Adenine deamination,
- B3LYP,
- G3MP2,
- Ammonia-assistance,
- Methanol-assistance
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沈阳化工大学材料科学与工程学院沈阳 110142

Effects of CH3OH and NH3 on the Hydrolytic Deamination Mechanismof Adenine

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通讯作者: 陈斌, bchen63@163.com

Effects of CH₃OH and NH₃ on the Hydrolytic Deamination Mechanismof Adenine