[8-13C-7-15N]-6-chloro-9-(2'-deoxy-β-D-erythro-pentofuranosyl)purine

• 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: [8-13C-7-15N]-6-chloro-9-(2'-deoxy-β-D-erythro-pentofuranosyl)purine
• 英文别名: (2R,3S,5R)-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• 化学式: C₁₀H₁₁ClN₄O₃
• 分子量: 272.658
• InChiKey: PGEULCIODBNODW-CDIDYNCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [8-13C-7-15N]-6-chloro-9-(2'-deoxy-β-D-erythro-pentofuranosyl)purine 在 ¹⁵N-ammonium chloride 、 potassium hydrogencarbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 以91%的产率得到[8-13C-7,NH2-15N2]-2'-deoxyadenosine
  参考文献：
  名称：

  Use of ¹³C as an Indirect Tag in ¹⁵N Specifically Labeled Nucleosides. Syntheses of [8-¹³C-1,7,NH₂-¹⁵N₃]Adenosine, -Guanosine, and Their Deoxy Analogues

  摘要：

  We have previously reported the use of a C-13 tag at the C2 of N-15-multilabeled purine nucleosides to distinguish the adjacent-labeled N-15 atoms from those in an untagged nucleoside. We now introduce the use of an indirect tag at the C8 of (15)N7-labeled purine nucleosides. This tag allows unambiguous differentiation between a pair of (15)N7-labeled purines in which only one is (13)C8 labeled. Although the very small C8-N7 coupling (< 1 Hz) precludes its direct detection in 1D N-15 spectra, 2D H-1-N-15 NMR experiments display the large C8-H8 coupling (>200 Hz) because H8 is coupled to both N7 and C8. The (13)C8 atom is introduced by means of a ring closure of the exocyclic amino groups of a pyrimidinone using [C-13] sodium ethyl xanthate. Here, we present methods for the syntheses of [8-C-13-1,7,NH2- N-15(3)]adenosine, -guanosine, and their deoxy analogues.

  DOI：

  10.1021/jo0345446
• 作为产物：
  描述：

  beta-胸苷 、 [8-13C-7-15N]-6-chloropurine 在 thymidine phosphorylase sodium hydroxide 、 dipotassium hydrogenphosphate 、 purine nucleoside phosphorylase 作用下， 以 水 为溶剂， 反应 48.0h， 以83%的产率得到[8-13C-7-15N]-6-chloro-9-(2'-deoxy-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  Use of ¹³C as an Indirect Tag in ¹⁵N Specifically Labeled Nucleosides. Syntheses of [8-¹³C-1,7,NH₂-¹⁵N₃]Adenosine, -Guanosine, and Their Deoxy Analogues

  摘要：

  We have previously reported the use of a C-13 tag at the C2 of N-15-multilabeled purine nucleosides to distinguish the adjacent-labeled N-15 atoms from those in an untagged nucleoside. We now introduce the use of an indirect tag at the C8 of (15)N7-labeled purine nucleosides. This tag allows unambiguous differentiation between a pair of (15)N7-labeled purines in which only one is (13)C8 labeled. Although the very small C8-N7 coupling (< 1 Hz) precludes its direct detection in 1D N-15 spectra, 2D H-1-N-15 NMR experiments display the large C8-H8 coupling (>200 Hz) because H8 is coupled to both N7 and C8. The (13)C8 atom is introduced by means of a ring closure of the exocyclic amino groups of a pyrimidinone using [C-13] sodium ethyl xanthate. Here, we present methods for the syntheses of [8-C-13-1,7,NH2- N-15(3)]adenosine, -guanosine, and their deoxy analogues.

  DOI：

  10.1021/jo0345446