(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-[(2-chloroethylamino)methyl]tetrahydrofuran-3,4-diol | 1172048-12-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-[(2-chloroethylamino)methyl]tetrahydrofuran-3,4-diol
• 英文别名: 5'-(2-chloroethyl)amino-5'-deoxyadenosine；(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[(2-chloroethylamino)methyl]oxolane-3,4-diol
• CAS: 1172048-12-2
• 化学式: C₁₂H₁₇ClN₆O₃
• 分子量: 328.758
• InChiKey: LPKLNXOGYBUJJY-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-[(2-chloroethylamino)methyl]tetrahydrofuran-3,4-diol 在 disodium hydrogenphosphate 、 磷酸 、 重水 、 sodium chloride 作用下， 以 氘代二甲亚砜 为溶剂， 生成 (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[(2-hydroxyethylamino)methyl]oxolane-3,4-diol 、 、 (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(aziridin-1-ylmethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  New S-Adenosyl-l-methionine Analogues: Synthesis and Reactivity Studies

  摘要：

  Two new and complementary synthetic strategies for 5'-N-chloroethylamino-5'-deoxyadenosines are presented. Additionally, the reaction kinetics of their conversion into aziridines under typical enzyme assay conditions is reported using time-resolved NMR spectroscopy. A stable photocaged derivative of 5'-N-chloroethylamino-5'-deoxyadenosine has also been synthesized, and its stability and activation In aqueous solution at physiological pH have been examined.

  DOI：

  10.1021/ol9009859
• 作为产物：
  描述：

  9-{(3aR,4R,6R,6aR)-6-[(2-chloroethylamino)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine 在 水 、 三氟乙酸 作用下， 反应 3.0h， 生成 (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-[(2-chloroethylamino)methyl]tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  New S-Adenosyl-l-methionine Analogues: Synthesis and Reactivity Studies

  摘要：

  Two new and complementary synthetic strategies for 5'-N-chloroethylamino-5'-deoxyadenosines are presented. Additionally, the reaction kinetics of their conversion into aziridines under typical enzyme assay conditions is reported using time-resolved NMR spectroscopy. A stable photocaged derivative of 5'-N-chloroethylamino-5'-deoxyadenosine has also been synthesized, and its stability and activation In aqueous solution at physiological pH have been examined.

  DOI：

  10.1021/ol9009859