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首页> 外文期刊>The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory >Reaction mechanism of uracil bromination by HBrO: A new way to generate the enol-keto form of 5-bromouracil
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Reaction mechanism of uracil bromination by HBrO: A new way to generate the enol-keto form of 5-bromouracil

机译：溴化氢溴化尿嘧啶的反应机理：生成5-溴尿嘧啶烯醇酮形式的新方法

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摘要

Knowledge on the uracil bromination reaction is helpful for understanding the origin of the mutagenicity of 5-bromouracil (BrU). To get more details about this reaction, we explore the corresponding reaction mechanism by theoretical method. A total of seven pathways were studied for this purpose. The diketo form of BrU is observed as the main product in these pathways, which agrees well with experimental results. The most energy-favorable reaction pathway is found to be that Br and OH attacked the opposite sides of uracil. The reaction intermediate reported in the experiment is predicted to be reasonably stable. In the following step, a dehydration process occurs between H11 and O13-H14 when there are no explicit H2O taking part. However, when there are explicit water molecules in the environment, explicit H2O will lower the reaction barrier in the formation of reaction intermediates and the final product BrU. A proton-transfer process from C5 to O10 is facilitated by explicit H2O, which results in enol-keto form intermediate of this modified base (defined as BrU*). These results indicate a new way to generate the enol-keto form of BrU.
机译：关于尿嘧啶溴化反应的知识有助于理解5-溴尿嘧啶（BrU）致突变性的起源。为了获得有关该反应的更多细节，我们通过理论方法探索了相应的反应机理。为此共研究了七个途径。在这些途径中，BrU的二酮形式被视为主要产物，与实验结果非常吻合。发现最有利于能量的反应途径是Br和OH攻击尿嘧啶的相反侧。预计实验中报道的反应中间体是相当稳定的。在接下来的步骤中，当没有明确的H2O参与时，H11和O13-H14之间会发生脱水过程。但是，当环境中存在明确的水分子时，明确的H2O会降低反应中间体和最终产物BrU形成过程中的反应壁垒。明显的H2O促进了从C5到O10的质子转移过程，这导致该修饰碱基（定义为BrU *）的烯醇-酮形式中间体。这些结果表明产生BrU的烯醇-酮形式的新方法。

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