(3-amino-5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxytetrahydrofuran-2-yl)methyl phosphate | 26113-03-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: (3-amino-5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxytetrahydrofuran-2-yl)methyl phosphate
• 英文别名: Puromycin aminonucleoside 5'-monophosphate；[(2S,3S,4R,5R)-3-amino-5-[6-(dimethylamino)purin-9-yl]-4-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 26113-03-1
• 化学式: C₁₂H₁₉N₆O₆P
• 分子量: 374.293
• InChiKey: BFPIKGKMRKBBBF-GRIPGOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  25
• 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：
  169
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-TBDMS-α-(R)-Me-β-HPA-OSu 、 (3-amino-5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxytetrahydrofuran-2-yl)methyl phosphate 在 碳酸氢钠 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 以5%的产率得到(5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxy-3-((R)-3-hydroxy-2-methylpropanamido)tetrahydrofuran-2-yl)methyl phosphate
  参考文献：
  名称：

  Synthesis of puromycin derivatives with backbone-elongated substrates and associated translation inhibitory activities

  摘要：

  We have synthesized a series of 5'-phosphorylated and 5'-cytidylyl-(3'-5')-cytidylyl-(3'-5')-puromycin derivatives that have backbone-elongated substrates. All the synthesized puromycin derivatives showed good solubility in water and were applied to translation inhibitory assay in a reconstituted Escherichia coli translation system. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.006
• 作为产物：
  描述：

  在 氨 、 水 作用下， 以 甲醇 为溶剂， 生成 (3-amino-5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxytetrahydrofuran-2-yl)methyl phosphate
  参考文献：
  名称：

  Synthesis of puromycin derivatives with backbone-elongated substrates and associated translation inhibitory activities

  摘要：

  We have synthesized a series of 5'-phosphorylated and 5'-cytidylyl-(3'-5')-cytidylyl-(3'-5')-puromycin derivatives that have backbone-elongated substrates. All the synthesized puromycin derivatives showed good solubility in water and were applied to translation inhibitory assay in a reconstituted Escherichia coli translation system. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.006

文献信息

• Synthesis of puromycin derivatives with backbone-elongated substrates and associated translation inhibitory activities
  作者：Keigo Mizusawa、Kenji Abe、Shinsuke Sando、Yasuhiro Aoyama

  DOI：10.1016/j.bmc.2009.02.006

  日期：2009.3

  We have synthesized a series of 5'-phosphorylated and 5'-cytidylyl-(3'-5')-cytidylyl-(3'-5')-puromycin derivatives that have backbone-elongated substrates. All the synthesized puromycin derivatives showed good solubility in water and were applied to translation inhibitory assay in a reconstituted Escherichia coli translation system. (C) 2009 Elsevier Ltd. All rights reserved.