2'-deoxyguanosine 5'-methylmonophosphate | 65128-56-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 2'-deoxyguanosine 5'-methylmonophosphate
• 英文别名: MepdG；deoxyguanosine 5'-(methyl hydrogen phosphate)；Methyl 2'-deoxy-5'-guanylate；[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl methyl hydrogen phosphate
• CAS: 65128-56-5
• 化学式: C₁₁H₁₆N₅O₇P
• 分子量: 361.251
• InChiKey: OJKOFFWPUHCGKE-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  171
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  甲基亚硝基脲 、 2ˊ-脱氧鸟苷-5ˊ-一磷酸 在 sodium hydroxide 、 phosphate buffer 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 2'-deoxyguanosine 5'-methylmonophosphate
  参考文献：
  名称：

  The mechanism of decomposition of N-methyl-N-nitrosourea (MNU) in water and a study of its reactions with 2′-deoxyguanosine, 2′-deoxyguanosine 5′-monophosphate and d(GTGCAC)

  摘要：

  The carcinogenicity of N-methyl-N-nitrosourea (MNU) arises from its ability to methylate DNA. This occurs in an aqueous environment and therefore an appreciation of the mode of decomposition of MNU in water is essential to understanding the mechanism of DNA methylation and its base sequence dependence. The kinetics of MNU hydrolyses are shown to be first order in MNU with a steep rise in rate above pH 8. Using NMR for in situ monitoring of reaction intermediates and products from hydrolyses of [(CO)-C-13]MNU, [(NH2)-N-15]MNU and [(CH3)-C-13]MNU, it is proved that base-induced hydrolysis of MNU is initiated by deprotonation at the carbamoyl group. The critical reactive species are shown to be the methyldiazonium ion (Me-N-2(+)) and cyanate (NCO-). Investigations of reactions of [(CH3)-C-13]MNU with 2'-deoxyguanosine (dGuo) and 2'-deoxyguanosine 5'-monophosphate (dGuo-5P) showed that: a) the site of methylation of dGuo is highly pH-dependent (relatively more N-1 and O-6-methylation compared to N-7 occurs at higher pH); b) the principal site of methylation of dGuo-5P by MNU is at phosphate: c) incorporation of deuterium into methyl groups occurs in D2O at higher pH. Methylation of the oligonucleotide d(GT[N-15]GCAC) by MNU in D2O showed partial deuteriation of the N-7-methyl groups of the guanines, whilst methylation by MNU in water indicated no significant preference for either guanine with respect to N-7-methylation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00018-5

文献信息

• Methylation of Deoxynucleotides with Trimethyl Phosphate in Aqueous Phase
  作者：Toshizumi Tanabe、Kiyoshi Yamauchi、Masayoshi Kinoshita

  DOI：10.1246/bcsj.56.1826

  日期：1983.6

  Action of trimethyl phosphate on thymidine 5′-phosphate, deoxycytidine 5′-phosphate, deoxyadenosine 5′-phosphate, and deoxyguanosine 5′-phosphate at 37–60 °C, and pH 7–10 gave their methyl esters and base-methylated derivatives. Esterification took place in all deoxyribonucleotides to the almost same extent and its rate was enhanced by the reaction temperature, while being independent of pH in the

  磷酸三甲酯在 37-60 °C 和 pH 7-10 下对胸苷 5'-磷酸、脱氧胞苷 5'-磷酸、脱氧腺苷 5'-磷酸和脱氧鸟苷 5'-磷酸的作用得到它们的甲酯和碱甲基化衍生物. 酯化在所有脱氧核糖核苷酸中发生的程度几乎相同，其速率随反应温度而提高，同时与 7-10 范围内的 pH 值无关。另一方面，碱基部分的甲基化受反应温度和反应介质 pH 值的影响。四种碱基的反应顺序ws；pH 7时，胞嘧啶碱基（N-3）>鸟嘌呤碱基（N-7）>腺嘌呤碱基（N-1）>>胸腺嘧啶碱基（N-3）；pH 10时，胸腺嘧啶碱基（N-3）>鸟嘌呤碱基（N-1>N-7）>胞嘧啶碱基（N-3）>腺嘌呤碱基（N-1）。
• The mechanism of decomposition of N-methyl-N-nitrosourea (MNU) in water and a study of its reactions with 2′-deoxyguanosine, 2′-deoxyguanosine 5′-monophosphate and d(GTGCAC)
  作者：Bernard T. Golding、Christine Bleasdale、Joseph McGinnis、Susanna Müller、Hue Thu Rees、Nicholas H. Rees、Peter B. Farmer、William P. Watson

  DOI：10.1016/s0040-4020(97)00018-5

  日期：1997.3

  The carcinogenicity of N-methyl-N-nitrosourea (MNU) arises from its ability to methylate DNA. This occurs in an aqueous environment and therefore an appreciation of the mode of decomposition of MNU in water is essential to understanding the mechanism of DNA methylation and its base sequence dependence. The kinetics of MNU hydrolyses are shown to be first order in MNU with a steep rise in rate above pH 8. Using NMR for in situ monitoring of reaction intermediates and products from hydrolyses of [(CO)-C-13]MNU, [(NH2)-N-15]MNU and [(CH3)-C-13]MNU, it is proved that base-induced hydrolysis of MNU is initiated by deprotonation at the carbamoyl group. The critical reactive species are shown to be the methyldiazonium ion (Me-N-2(+)) and cyanate (NCO-). Investigations of reactions of [(CH3)-C-13]MNU with 2'-deoxyguanosine (dGuo) and 2'-deoxyguanosine 5'-monophosphate (dGuo-5P) showed that: a) the site of methylation of dGuo is highly pH-dependent (relatively more N-1 and O-6-methylation compared to N-7 occurs at higher pH); b) the principal site of methylation of dGuo-5P by MNU is at phosphate: c) incorporation of deuterium into methyl groups occurs in D2O at higher pH. Methylation of the oligonucleotide d(GT[N-15]GCAC) by MNU in D2O showed partial deuteriation of the N-7-methyl groups of the guanines, whilst methylation by MNU in water indicated no significant preference for either guanine with respect to N-7-methylation. (C) 1997 Elsevier Science Ltd.