N⁷-Me-dGuo | 28074-91-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁷-Me-dGuo
• 英文别名: 7-Methyldeoxyguanosin；2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-1H-purin-9-ium-6-one
• CAS: 28074-91-1
• 化学式: C₁₁H₁₆N₅O₄
• 分子量: 282.279
• InChiKey: OMQUVUUQUJTKDH-RRKCRQDMSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基亚硝基脲 、 2'-脱氧鸟苷 在 sodium hydroxide 、 phosphate buffer 作用下， 以 甲醇 、 水 为溶剂， 生成 2'-脱氧-6-O-甲基-鸟苷 、 N¹-methyl-2'-deoxyguanosine 、 磷酸单甲酯 、 磷酸二甲酯 、 7-甲基鸟嘌呤 、 N⁷-Me-dGuo
  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

• 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.