Deamination features of 5-hydroxymethylcytosine, a radical and enzymatic DNA oxidation product
Deamination features of 5-hydroxymethylcytosine, a radical and enzymatic DNA oxidation product
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DOI：
10.1007/s00894-014-2290-9
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发表时间：
2014-06-01
影响因子：
2.2
通讯作者：
Eriksson, Leif A.
中科院分区：
文献类型：
--
作者：
Grand, Andre;Jorge, Nelly;Eriksson, Leif A.
5-甲基胞嘧啶衍生物5-羟甲基胞嘧啶（5 hmCyt），通过酶促氧化产生，有时被称为第六个核碱基，因为它广泛存在于脑和胚胎干细胞的DNA中。在这项研究中，我们使用密度泛函为基础的方法和反应性指数从概念DFT探索5 hmCyt的水解脱氨基的机制和关键特征。所获得的数据用于比较和对比这种脱氨基反应与其他胞嘧啶衍生物。5 hmCyt的脱氨过程类似于其他不饱和衍生物的相应过程，因为氨基形式是反应性的，并且水的添加是限速步骤。然而，也注意到由于当前系统的旋转异构不对称性而导致的几个差异。
The 5-methylcytosine derivative 5-hydroxymethylcytosine (5hmCyt), which is generated via enzymatic oxidation, is sometimes referred to as the sixth nucleobase due to its widespread presence in the DNA of brain and embryonic stem cells. In this study, we used density functional based methods and reactivity indices from conceptual DFT to explore the mechanism and key features of the hydrolytic deamination of 5hmCyt. The data obtained are used to compare and contrast this deamination reaction with those of other cytosine derivatives. The deamination process for 5hmCyt is similar to the corresponding processes for other unsaturated derivatives in that the amino form is the reactive one and water addition is the rate-limiting step. However, several differences due to the rotameric asymmetry of the current system are also noted.