The Possibility of the Decomposition of 2 '-Deoxyribose Moiety of Thymidine Induced by the Low Energy Electron Attachment
文献类型：期刊论文
| 作者 | Liang, Guoming1; Bao, Xiaoguang2; Gu, Jiande2
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| 刊名 | JOURNAL OF COMPUTATIONAL CHEMISTRY
 |
| 出版日期 | 2008-12 |
| 卷号 | 29期号:16页码:2648-2655 |
| 关键词 | thymidine low energy electrons attachment bond rupture |
| ISSN号 | 0192-8651 |
| DOI | 10.1002/jcc.21009 |
| 文献子类 | Article |
| 英文摘要 | To evaluate the possibility of the decomposition of 2-deoxyribose moiety of thymidine induced by low energy electrons (LEE) attachment, the transition states and the energy barriers of the bond breaking processes of the ribose of the nucleoside have been studied theoretically by applying the density functional theory with the double zeta basis sets (DZP + +). The energy barriers for the breakage of the C-C bonds (C-1'-C-2', C-2'-C-3', C-3'-C-4', and C-4'-C-5') of the ribose group of the radical anion of thymidine are found to be high (ca. 42-57 kcal/mol). The total energies of the C-C bond-broken products are significantly higher than that of the radical anion dT(center dot-). The decomposition of dT(center dot-) through the C-C bond rupture is unlikely to take place. The rupture of the C-1'-O-4' bond of dT(center dot-) needs an activation energy as low as 10.4 kcal/mol. However, the reversed reaction (C-1'-O-4' bond formation) needs the activation energy low as 0.3 kcal/mol. Therefore, the intermediate product LM1(C1'-O4') is unlikely to be stable and the C-1'-O-4' bond-broken is not favored. The activation energy of the C-4'-O-4' bond rupture process amounts to 20.5 kcal/mol. The total energy of the C-4'-O-4' bond broken product is about 6.5 kcal/mol lower than that of the reactant dT(center dot-). The subsequent Nl-glycosidic bond breaking process is found to have a very low energy barrier. Therefore, the LEE-induced base release through the C-4'-O-4' bond rupture might be a possible pathway. (c) 2008 Wiley Periodicals, Inc. |
| WOS关键词 | DNA-STRAND BREAKS ; PHASE DEOXYRIBOSE ANALOGS ; GLYCOSIDIC BOND-CLEAVAGE ; GAS-PHASE ; PYRIMIDINE NUCLEOTIDES ; STIMULATED DESORPTION ; DAMAGE ; DENSITY ; THYMINE ; NUCLEOSIDES |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000260898300005 |
| 出版者 | WILEY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/279417]  |
| 专题 | 药物发现与设计中心 |
| 通讯作者 | Gu, Jiande |
| 作者单位 | 1.Chongqing Normal Univ, Coll Chem, Chongqing 400047, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Drug Design & Discovery Ctr,State Key Lab Drug Re, Shanghai 201203, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Liang, Guoming,Bao, Xiaoguang,Gu, Jiande. The Possibility of the Decomposition of 2 '-Deoxyribose Moiety of Thymidine Induced by the Low Energy Electron Attachment[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY,2008,29(16):2648-2655. |
| APA | Liang, Guoming,Bao, Xiaoguang,&Gu, Jiande.(2008).The Possibility of the Decomposition of 2 '-Deoxyribose Moiety of Thymidine Induced by the Low Energy Electron Attachment.JOURNAL OF COMPUTATIONAL CHEMISTRY,29(16),2648-2655. |
| MLA | Liang, Guoming,et al."The Possibility of the Decomposition of 2 '-Deoxyribose Moiety of Thymidine Induced by the Low Energy Electron Attachment".JOURNAL OF COMPUTATIONAL CHEMISTRY 29.16(2008):2648-2655. |
入库方式： OAI收割
来源：上海药物研究所
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