腺苷5'-单磷酸酯2',3'-二醛 | 13011-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 腺苷5'-单磷酸酯2',3'-二醛
• 英文名称: periodate-oxidized AMP
• 英文别名: phosphoric acid mono-{2-[1-(6-amino-purin-9-yl)-2-oxo-ethoxy]-3-oxo-propyl} ester；Adenosine 5'-monophosphate 2',3'-dialdehyde；[(2R)-2-[(1R)-1-(6-aminopurin-9-yl)-2-oxoethoxy]-3-oxopropyl] dihydrogen phosphate
• CAS: 13011-02-4
• 化学式: C₁₀H₁₂N₅O₇P
• 分子量: 345.208
• InChiKey: MEHSJNLHNAMNGO-NKWVEPMBSA-N

物化性质

• 沸点：
  654.4±65.0 °C(Predicted)
• 密度：
  1.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  180
• 氢给体数：
  3
• 氢受体数：
  11

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-叠氮基丙胺 、 腺苷5'-单磷酸酯2',3'-二醛 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 水 为溶剂， 反应 3.0h， 生成 Phosphoric acid mono-[(2S,6R)-6-(6-amino-purin-9-yl)-4-(3-azido-propyl)-morpholin-2-ylmethyl] ester
  参考文献：
  名称：

  Delivery of 2-5A cargo into living cells using the Tat cell penetrating peptide: 2-5A-tat

  摘要：

  2',5'-Oligoadenylate tetramer (2-5A) has been chemically conjugated to short HIV-1 Tat peptides to provide 2-5A-tat chimeras. Two different convergent synthetic approaches have been employed to provide such 2-5A-tat bioconjugates. One involved generation of a bioconjugate through reaction of a cysteine terminated Tat peptide with a alpha-chloroacetyl derivative of 2-5A. The second synthetic strategy was based upon a cycloaddition reaction of an azide derivative of 2-5A with a Tat peptide bearing an alkyne function. Either bioconjugate of 2-5A-tat was able to activate human RNase L. The union of 2-5A and Tat peptide provided an RNase L-active chimeric nucleopeptide with the ability to be taken up by cells by virtue of the Tat peptide and to activate RNase L in intact cells. This strategy provides a valuable vehicle for the entry of the charged 2-5A molecule into cells and may provide a means for targeted destruction of HIV RNA in vivo. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.058
• 作为产物：
  描述：

  5'-腺嘌呤核苷酸 在 sodium periodate 作用下， 以 水 为溶剂， 反应 0.5h， 生成 腺苷5'-单磷酸酯2',3'-二醛
  参考文献：
  名称：

  Delivery of 2-5A cargo into living cells using the Tat cell penetrating peptide: 2-5A-tat

  摘要：

  2',5'-Oligoadenylate tetramer (2-5A) has been chemically conjugated to short HIV-1 Tat peptides to provide 2-5A-tat chimeras. Two different convergent synthetic approaches have been employed to provide such 2-5A-tat bioconjugates. One involved generation of a bioconjugate through reaction of a cysteine terminated Tat peptide with a alpha-chloroacetyl derivative of 2-5A. The second synthetic strategy was based upon a cycloaddition reaction of an azide derivative of 2-5A with a Tat peptide bearing an alkyne function. Either bioconjugate of 2-5A-tat was able to activate human RNase L. The union of 2-5A and Tat peptide provided an RNase L-active chimeric nucleopeptide with the ability to be taken up by cells by virtue of the Tat peptide and to activate RNase L in intact cells. This strategy provides a valuable vehicle for the entry of the charged 2-5A molecule into cells and may provide a means for targeted destruction of HIV RNA in vivo. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.058