5-(hydroperoxymethyl)-2′-deoxycytidine | 183945-25-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(hydroperoxymethyl)-2′-deoxycytidine
• 英文别名: 2'-Deoxy-5-(hydroperoxymethyl)cytidine；4-amino-5-(hydroperoxymethyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 183945-25-7
• 化学式: C₁₀H₁₅N₃O₆
• 分子量: 273.246
• InChiKey: LWBPLZRMBYBJGR-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-甲基-2'-脱氧胞苷 在 air 、 甲萘醌 作用下， 以 水 为溶剂， 反应 0.42h， 以7%的产率得到5-(hydroperoxymethyl)-2′-deoxycytidine
  参考文献：
  名称：

  2-甲基-1,4-萘醌对 5-甲基-2'-脱氧胞苷的光敏氧化：5-（氢过氧甲基）-2'-脱氧胞苷和稳定甲基氧化产物的表征§

  摘要：

  5-甲基胞嘧啶是真核生物 DNA 的次要核碱基，在基因表达调控中起核心作用。在作为 I 型光敏剂的甲萘醌 (MQ) 存在下，对 5-甲基-2'-脱氧胞苷的充气水溶液进行 UV-A 照射会导致形成几种稳定的氧化产物。本研究的重点是分离和表征主要类别的分解产物，其形成涉及甲基的氧化。这些包括 5-(氢过氧甲基)-2'-脱氧胞苷和两种稳定的分解产物，即 5-(羟甲基)-2'-脱氧胞苷和 5-甲酰基-2'-脱氧胞苷。后者修饰的核苷的结构分配是从广泛的光谱测量（1H 和 13C NMR、UV 光谱和质谱）推断出来的。此外，从详细的 1 H NMR 分析推断氧化核苷的构象分析。所有上述光氧化产物似乎都是由去质...

  DOI：

  10.1021/ja962073h

文献信息

• Photosensitized Oxidation of 5-Methyl-2‘-deoxycytidine by 2-Methyl-1,4-naphthoquinone:  Characterization of 5-(Hydroperoxymethyl)-2‘-deoxycytidine and Stable Methyl Group Oxidation Products
  作者：Carine Bienvenu、J. Richard Wagner、Jean Cadet

  DOI：10.1021/ja962073h

  日期：1996.1.1

  of the major class of decomposition products whose formation involves the oxidation of the methyl group. These include 5-(hydroperoxymethyl)-2‘-deoxycytidine and two stable decomposition products namely, 5-(hydroxymethyl)-2‘-deoxycytidine and 5-formyl-2‘-deoxycytidine. Structural assignment of the latter modified nucleosides was inferred from extensive spectroscopic measurements (1H and 13C NMR, UV spectroscopy

  5-甲基胞嘧啶是真核生物 DNA 的次要核碱基，在基因表达调控中起核心作用。在作为 I 型光敏剂的甲萘醌 (MQ) 存在下，对 5-甲基-2'-脱氧胞苷的充气水溶液进行 UV-A 照射会导致形成几种稳定的氧化产物。本研究的重点是分离和表征主要类别的分解产物，其形成涉及甲基的氧化。这些包括 5-(氢过氧甲基)-2'-脱氧胞苷和两种稳定的分解产物，即 5-(羟甲基)-2'-脱氧胞苷和 5-甲酰基-2'-脱氧胞苷。后者修饰的核苷的结构分配是从广泛的光谱测量（1H 和 13C NMR、UV 光谱和质谱）推断出来的。此外，从详细的 1 H NMR 分析推断氧化核苷的构象分析。所有上述光氧化产物似乎都是由去质...
• US7563887B1
  申请人：——

  公开号：US7563887B1

  公开（公告）日：2009-07-21
• Potent methyl oxidation of 5-methyl-2′-deoxycytidine by halogenated quinoid carcinogens and hydrogen peroxide via a metal-independent mechanism
  作者：Jie Shao、Chun-Hua Huang、Balaraman Kalyanaraman、Ben-Zhan Zhu

  DOI：10.1016/j.freeradbiomed.2013.01.010

  日期：2013.7

  Halogenated quinones are a class of carcinogenic intermediates and are newly identified chlorination disinfection by-products in drinking water. We found recently that the highly reactive and biologically important hydroxyl radical ((OH)-O-center dot) can be produced by halogenated quinones and H2O2 independent of transition metal ions. However, it is not clear whether these quinoid carcinogens and H2O2 can oxidize the nucleoside 5-methyl-2'-deoxycytidine (5mdC) to its methyl oxidation products and, if so, what the underlying molecular mechanism is. Here we show that three methyl oxidation products, 5-(hydroperoxymethyl)-, 5-(hydroxymethyl)-, and 5-formyl-2'-deoxycytidine, could be produced when 5mdC was treated with tetrachloro-1,4-benzoquinone (TCBQ) and H2O2. The formation of the oxidation products was markedly inhibited by typical (OH)-O-center dot scavengers and under anaerobic conditions. Analogous effects were observed with other halogenated quinones and the classic Fenton system. Based on these data, we propose that the oxidation of 5mdC by TCBQ/H2O2 might be through the following mechanism: (OH)-O-center dot produced by TCBQ/H2O2 may first abstract hydrogen from the methyl group of 5mdC, leading to the formation of 5-(2'-deoxycytidylyl)methyl radical, which may combine with O-2 to form the peroxyl radical. The unstable peroxyl radical transforms into the corresponding hydroperoxide 5-(hydroperoxymethyl)-2'-deoxycytidine, which reacts with TCBQ and results in the formation of 5-(hydroxymethyl)-2'-deoxycytidine and 5-formyl-2'-deoxycytidine. This is the first report that halogenated quinoid carcinogens and H2O2 can induce potent methyl oxidation of 5mdC via a metal-independent mechanism, which may partly explain their potential carcinogenicity. (C) 2013 Elsevier Inc. All rights reserved.