Phosphoric acid mono-{(2S,6R)-6-(6-amino-purin-9-yl)-4-[4-(2-chloro-acetylamino)-benzyl]-morpholin-2-ylmethyl} ester | 917877-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: Phosphoric acid mono-{(2S,6R)-6-(6-amino-purin-9-yl)-4-[4-(2-chloro-acetylamino)-benzyl]-morpholin-2-ylmethyl} ester
• CAS: 917877-29-3
• 化学式: C₁₉H₂₃ClN₇O₆P
• 分子量: 511.862
• InChiKey: ZYMLUSBTYPLMRL-GOEBONIOSA-N

物化性质

• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  177.95
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid mono-{(2S,6R)-6-(6-amino-purin-9-yl)-4-[4-(2-chloro-acetylamino)-benzyl]-morpholin-2-ylmethyl} ester 、 HS-Cys-Gly-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Arg-Arg-OH 在 sodium dihydrogenphosphate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以73%的产率得到
  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 hydroxide 、 sodium periodate 作用下， 以 水 为溶剂， 反应 4.0h， 生成 Phosphoric acid mono-{(2S,6R)-6-(6-amino-purin-9-yl)-4-[4-(2-chloro-acetylamino)-benzyl]-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