1D-O-(1,2-di-O-palmitoyl-sn-(2S)-glycerol-3-O-cyanoethylphospho)-3-(bis(cyanoethyl)phosphothionate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol | 922712-40-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 1D-O-(1,2-di-O-palmitoyl-sn-(2S)-glycerol-3-O-cyanoethylphospho)-3-(bis(cyanoethyl)phosphothionate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol
• CAS: 922712-40-1
• 化学式: C₅₈H₁₀₇N₃O₂₃P₄S
• 分子量: 1370.45
• InChiKey: VHTARTPZIIWXTD-FPTURRCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.88
• 重原子数：
  89.0
• 可旋转键数：
  61.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  322.86
• 氢给体数：
  0.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  1D-O-(1,2-di-O-palmitoyl-sn-(2S)-glycerol-3-O-cyanoethylphospho)-3-(bis(cyanoethyl)phosphothionate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol 在 bis(trimethylsilyl)trifluoroacetamide 、 三甲基溴硅烷 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.67h， 生成 1D-O-(1,2-di-O-palmitoyl-sn-(2S)-glycerol-3-phospho)-3-phosphothionate-4,5-bisphosphate-myo-inositol
  参考文献：
  名称：

  Synthesis and Biological Activity of PTEN-Resistant Analogues of Phosphatidylinositol 3,4,5-Trisphosphate

  摘要：

  The activation of phosphatidylinositol 3-kinase (PI 3-K) and subsequent production of PtdIns(3,4,5)P3 launches a signal transduction cascade that impinges on a plethora of downstream effects on cell physiology. Control of PI 3-K and PtdIns(3,4,5)P3 levels is an important therapeutic target in treatments for allergy, inflammation, cardiovascular, and malignant human diseases. We designed metabolically stabilized, that is, phosphatase resistant, analogues of PtdIns(3,4,5)P3 as probes for long-lived potential agonists or potential antagonists for cellular events mediated by PtdIns(3,4,5)P3. In particular, two types of analogues were prepared containing phosphomimetics that would be selectively resistant to the lipid 3-phosphatase PTEN. The total asymmetric synthesis of the 3-phosphorothioate-PtdIns(3,4,5)P3 and 3-methylenephosphonate-PtdIns(3,4,5)P3 analogues is described. These two analogues showed differential binding to PtdIns(3,4,5)P3 binding modules, and both were potential long-lived activators that mimicked insulin action in sodium transport in A6 cells.

  DOI：

  10.1021/ja065002j
• 作为产物：
  描述：

  1D-3-(bis(cyanoethyl)phosphothionate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol 、 [(R)-2,3-bis{(1-oxohexadecyl)oxy}propyloxy](2-cyanoethoxy)(diisopropylamino)phosphane 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 癸烷 为溶剂， 反应 13.0h， 以87%的产率得到1D-O-(1,2-di-O-palmitoyl-sn-(2S)-glycerol-3-O-cyanoethylphospho)-3-(bis(cyanoethyl)phosphothionate)-2,6-O-bis(methoxymethylene)-4,5-bis(dimethylphosphate)-myo-inositol
  参考文献：
  名称：

  Synthesis and Biological Activity of PTEN-Resistant Analogues of Phosphatidylinositol 3,4,5-Trisphosphate

  摘要：

  The activation of phosphatidylinositol 3-kinase (PI 3-K) and subsequent production of PtdIns(3,4,5)P3 launches a signal transduction cascade that impinges on a plethora of downstream effects on cell physiology. Control of PI 3-K and PtdIns(3,4,5)P3 levels is an important therapeutic target in treatments for allergy, inflammation, cardiovascular, and malignant human diseases. We designed metabolically stabilized, that is, phosphatase resistant, analogues of PtdIns(3,4,5)P3 as probes for long-lived potential agonists or potential antagonists for cellular events mediated by PtdIns(3,4,5)P3. In particular, two types of analogues were prepared containing phosphomimetics that would be selectively resistant to the lipid 3-phosphatase PTEN. The total asymmetric synthesis of the 3-phosphorothioate-PtdIns(3,4,5)P3 and 3-methylenephosphonate-PtdIns(3,4,5)P3 analogues is described. These two analogues showed differential binding to PtdIns(3,4,5)P3 binding modules, and both were potential long-lived activators that mimicked insulin action in sodium transport in A6 cells.

  DOI：

  10.1021/ja065002j