(7,NH2-15N2)-2'-deoxyadenosine N1-oxide | 197227-87-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (7,NH2-15N2)-2'-deoxyadenosine N1-oxide
• CAS: 197227-87-5
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 269.231
• InChiKey: UNOWTAUKAYUFPA-BJTXFVETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.71
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  133.36
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  potassium,azanylidynemethane 、 (7,NH2-15N2)-2'-deoxyadenosine N1-oxide 在 溴 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (2R,3S,5R)-5-(2-(15N)azanyl-(513C,415N)[1,2,4]oxadiazolo[3,2-f]purin-4-ium-7-yl)-2-(hydroxymethyl)oxolan-3-ol
  参考文献：
  名称：

  Use of a ¹³C Atom To Differentiate Two ¹⁵N-Labeled Nucleosides. Syntheses of [¹⁵NH₂]-Adenosine, [1,NH₂-¹⁵N₂]- and [2-¹³C-1,NH₂-¹⁵N₂]-Guanosine, and [1,7,NH₂-¹⁵N₃]- and [2-¹³C-1,7,NH₂-¹⁵N₃]-2‘-Deoxyguanosine

  摘要：

  We report the first examples of the specifically N-15 and C-13 multilabeled nucleosides: [1,NH2-N-15(2)]- and [2-C-13-1,NH2-N-15(2)-]-guanosine; [1,7,NH2-N-15(3)]- and [2-C-13-1,7,NH2-N-15(3)]-2'-deoxyguanosine. In each set, the [C-13] atom functions as a ''tag'' that allows the N1 and N2 N-15 atoms of two N-15-labeled guanines to be unambiguously differentiated in RNA and DNA fragments. The syntheses employ high-yield reactions in which protecting groups are not required and use relatively low cost sources of isotopes: [N-15]-ammonium chloride and [N-15]- Or [C-13,N-15]-potassium cyanide.

  DOI：

  10.1021/jo971206u
• 作为产物：
  描述：

  [6,7-¹⁵N]-2'-deoxyadenosine 在 ¹⁵N-ammonium chloride 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以87%的产率得到(7,NH2-15N2)-2'-deoxyadenosine N1-oxide
  参考文献：
  名称：

  Use of a ¹³C Atom To Differentiate Two ¹⁵N-Labeled Nucleosides. Syntheses of [¹⁵NH₂]-Adenosine, [1,NH₂-¹⁵N₂]- and [2-¹³C-1,NH₂-¹⁵N₂]-Guanosine, and [1,7,NH₂-¹⁵N₃]- and [2-¹³C-1,7,NH₂-¹⁵N₃]-2‘-Deoxyguanosine

  摘要：

  We report the first examples of the specifically N-15 and C-13 multilabeled nucleosides: [1,NH2-N-15(2)]- and [2-C-13-1,NH2-N-15(2)-]-guanosine; [1,7,NH2-N-15(3)]- and [2-C-13-1,7,NH2-N-15(3)]-2'-deoxyguanosine. In each set, the [C-13] atom functions as a ''tag'' that allows the N1 and N2 N-15 atoms of two N-15-labeled guanines to be unambiguously differentiated in RNA and DNA fragments. The syntheses employ high-yield reactions in which protecting groups are not required and use relatively low cost sources of isotopes: [N-15]-ammonium chloride and [N-15]- Or [C-13,N-15]-potassium cyanide.

  DOI：

  10.1021/jo971206u

文献信息

• Syntheses of [1,7-¹⁵N₂]- and [1,7,<i>NH</i><i>₂</i>-¹⁵N₃]Adenosine and 2‘-Deoxyadenosine via an <i>N</i>¹-Alkoxy-Mediated Dimroth Rearrangement
  作者：Alex R. Pagano、Hong Zhao、Anthony Shallop、Roger A. Jones

  DOI：10.1021/jo9718152

  日期：1998.5.1

  We have found that the N-1-methoxy derivatives of adenosine and 2'-deoxyadenosine undergo a Dimroth rearrangement in which the intermediate N,N-dimethylamino adducts are stable compounds. This mild and high-yield rearrangement allows efficient conversion of [7,NH2-N-15(2)]2'-deoxyadenosine and [7,NH2-N-15(2)]adenosine into the triply labeled [1,7,NH2-N-15(3)] derivatives. The [7,NH2-N-15(2)]nucleoside is first oxidized to the N-1-oxide with 3-chloroperoxybenzoic acid (MCPBA). Methylation of the N-1-oxide with methyl iodide or dimethyl sulfate is followed by treatment with dimethylamine to afford the 6-amino-N-1-methoxy-2-(N,N-dimethylamino) derivative. Dimroth rearrangement of these surprisingly stable intermediates is accomplished by refluxing in the presence of a dimethylammonium hydrohalide salt to give the [1,7-N-15(2)]-6-N-methoxy nucleosides in high yield. Removal of the N-6-methoxy function to afford both [1,7-N-15(2)]deoxyadenosine and [1,7-N-15(2)]adenosine was accomplished readily with Raney nickel. No hydroxyl protection is required for these transformations. Introduction of the third label at the N-6 was accomplished by conversion into the 6-(1,2,4-triazol-4-yl)purine nucleosides, followed by nucleophilic displacement of the 6-triazole with [N-15]ammonia to afford the triply labeled title compounds.