Isoguanine Formation from Adenine
文献类型：期刊论文
| 作者 | Cheng, Qianyi2; Gu, Jiande1 ; Compaan, Katherine R.2; Schaefer, Henry F., III2
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| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2012-04 |
| 卷号 | 18期号:16页码:4877-4886 |
| 关键词 | adenine nucleobases radicals tautomerization |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.201102415 |
| 文献子类 | Article |
| 英文摘要 | Several possible mechanisms underlying isoguanine formation when OH radical attacks the C2 position of adenine (AC2) are investigated theoretically for the first time. Two steps are involved in this process. In the first step, one of two low-lying AC2 center dot OH reactant complexes is formed, leading to C2H2 bond cleavage. Between the two reactant complexes there is a small isomerization barrier, which lies well below separated adenine plus OH radical. The complex dissociates to free molecular hydrogen and an isoguanine tautomer (isoG1 or isoG2). The local and activation barriers for the two pathways are very similar. This evidence suggests that the two pathways are competitive. After dehydrogenation, there are two possible routes for the second step of the reaction. One is direct hydrogen transfer, via enolketo tautomerization, which has high local barriers for both tautomers and is not favored. The other option is indirect hydrogen transfer involving microsolvation by one water molecule. The water lowers the reaction barrier by over 20 kcalmol-1, indicating that water-mediated hydrogen transfer is much more favorable. Both A+OH.isoG+H. reactions are exothermic and spontaneous. Among four isoguanine tautomers, isoG1 has the lowest energy. Our findings explain why only the N1H and O2H tautomers of isolated isoguanine and isoguanosine have been observed experimentally. |
| WOS关键词 | UNIMOLECULAR TRANSFORMATION REACTIONS ; HEXOSE-NUCLEIC-ACIDS ; OH RADICAL REACTION ; BASE-PAIR ; ELECTRON-AFFINITIES ; AQUEOUS-SOLUTION ; OPPOSITE 2-HYDROXYADENINE ; SEQUENCE CONTEXTS ; DNA BASES ; NUCLEOSIDES |
| 资助项目 | US National Science Foundation[CHE-0749868] ; National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program", China[2009ZX09301-001] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000302354500013 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/278133]  |
| 专题 | 药物发现与设计中心 中科院受体结构与功能重点实验室 新药研究国家重点实验室 |
| 通讯作者 | Gu, Jiande |
| 作者单位 | 1.CAS, Drug Design & Discovery Ctr, State Key Lab Drug Res, Shanghai Inst Mat Med,Shanghai Inst Biol Sci, Shanghai 201203, Peoples R China; 2.Univ Georgia, Ctr Computat Quantum Chem, Athens, GA 30602 USA |
| 推荐引用方式 GB/T 7714 | Cheng, Qianyi,Gu, Jiande,Compaan, Katherine R.,et al. Isoguanine Formation from Adenine[J]. CHEMISTRY-A EUROPEAN JOURNAL,2012,18(16):4877-4886. |
| APA | Cheng, Qianyi,Gu, Jiande,Compaan, Katherine R.,&Schaefer, Henry F., III.(2012).Isoguanine Formation from Adenine.CHEMISTRY-A EUROPEAN JOURNAL,18(16),4877-4886. |
| MLA | Cheng, Qianyi,et al."Isoguanine Formation from Adenine".CHEMISTRY-A EUROPEAN JOURNAL 18.16(2012):4877-4886. |
入库方式： OAI收割
来源：上海药物研究所
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