(2S,3R)-di(octadecanoyloxy)butane-1,4-diyl bis(dibenzylphosphate) | 190258-33-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-di(octadecanoyloxy)butane-1,4-diyl bis(dibenzylphosphate)
• 英文别名: [(2R,3S)-3-octadecanoyloxy-1,4-bis[[oxido-bis(phenylmethoxy)phosphaniumyl]oxy]butan-2-yl] octadecanoate
• CAS: 190258-33-4
• 化学式: C₆₈H₁₀₄O₁₂P₂
• 分子量: 1175.51
• InChiKey: UAODOKZBANFEHQ-HOAYPZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.5
• 重原子数：
  82
• 可旋转键数：
  55
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3R)-di(octadecanoyloxy)butane-1,4-diyl bis(dibenzylphosphate) 在 palladium on activated charcoal sodium hydroxide 、 Dowex 50WX₂₀ (sodium form) 、 氢气 作用下， 生成 sodium (2R,3S)-di(octadecanoyloxy)butane-1,4-diyl bisphosphate
  参考文献：
  名称：

  Stereodependent Fusion and Fission of Vesicles:  Calcium Binding of Synthetic Gemini Phospholipids Containing Two Phosphate Groups

  摘要：

  Three different stereoisomers of a phosphatidic acid analog bearing two phosphate groups have been synthesized from tartaric acid and erythritol. The obtained diastereomeric gemini surfactants differ in their aggregation behavior due to the different spatial orientations of their functional groups. The most remarkable difference in aggregation behavior is encountered when calcium ions are added to vesicle suspensions of the respective isomers. The vesicles formed from the (S,S) and (R,R) isomer undergo fusion, whereas those of the (R,S) isomer show vesicle fission. This remarkable behavior can be explained by a change in the molecular packing of the lipid molecules upon the complexation with calcium ions. An analysis of physical data obtained prior to and after the addition of the calcium ions reveals that the head groups of the diastereomeric surfactants respond differently to these ions: those of the (S,S) isomer increase in size, whereas those of the (R,S) isomer decrease in size. This phenomenon accounts for occurrence of fusion and fission of the vesicles, respectively.

  DOI：

  10.1021/ja962303s
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 28.0h， 生成 (2S,3R)-di(octadecanoyloxy)butane-1,4-diyl bis(dibenzylphosphate)
  参考文献：
  名称：

  Stereodependent Fusion and Fission of Vesicles:  Calcium Binding of Synthetic Gemini Phospholipids Containing Two Phosphate Groups

  摘要：

  Three different stereoisomers of a phosphatidic acid analog bearing two phosphate groups have been synthesized from tartaric acid and erythritol. The obtained diastereomeric gemini surfactants differ in their aggregation behavior due to the different spatial orientations of their functional groups. The most remarkable difference in aggregation behavior is encountered when calcium ions are added to vesicle suspensions of the respective isomers. The vesicles formed from the (S,S) and (R,R) isomer undergo fusion, whereas those of the (R,S) isomer show vesicle fission. This remarkable behavior can be explained by a change in the molecular packing of the lipid molecules upon the complexation with calcium ions. An analysis of physical data obtained prior to and after the addition of the calcium ions reveals that the head groups of the diastereomeric surfactants respond differently to these ions: those of the (S,S) isomer increase in size, whereas those of the (R,S) isomer decrease in size. This phenomenon accounts for occurrence of fusion and fission of the vesicles, respectively.

  DOI：

  10.1021/ja962303s

文献信息

• Stereodependent Fusion and Fission of Vesicles:  Calcium Binding of Synthetic Gemini Phospholipids Containing Two Phosphate Groups
  作者：N. A. J. M. Sommerdijk、T. H. L. Hoeks、M. Synak、M. C. Feiters、R. J. M. Nolte、B. Zwanenburg

  DOI：10.1021/ja962303s

  日期：1997.5.1

  Three different stereoisomers of a phosphatidic acid analog bearing two phosphate groups have been synthesized from tartaric acid and erythritol. The obtained diastereomeric gemini surfactants differ in their aggregation behavior due to the different spatial orientations of their functional groups. The most remarkable difference in aggregation behavior is encountered when calcium ions are added to vesicle suspensions of the respective isomers. The vesicles formed from the (S,S) and (R,R) isomer undergo fusion, whereas those of the (R,S) isomer show vesicle fission. This remarkable behavior can be explained by a change in the molecular packing of the lipid molecules upon the complexation with calcium ions. An analysis of physical data obtained prior to and after the addition of the calcium ions reveals that the head groups of the diastereomeric surfactants respond differently to these ions: those of the (S,S) isomer increase in size, whereas those of the (R,S) isomer decrease in size. This phenomenon accounts for occurrence of fusion and fission of the vesicles, respectively.