| 1095854-25-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• CAS: 1095854-25-3
• 化学式: C₇₃H₁₂₁N₃O₁₀
• 分子量: 1200.78
• InChiKey: RKNSKIDAHYMBIY-KCGKBOMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.51
• 重原子数：
  86.0
• 可旋转键数：
  14.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  231.9
• 氢给体数：
  9.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Water-Templated Transmembrane Nanopores from Shape-Persistent Oligocholate Macrocycles

  摘要：

  Hydrophobic interactions normally are not considered a major driving force for self-assembling in a hydrophobic environment. When macrocyclic oligocholates were placed within lipid membranes, however, the macrocycles pulled water molecules from the aqueous phase into their hydrophilic internal cavities. These water molecules had strong tendencies to aggregate in a hydrophobic environment and templated the macrocycles to self-assemble into transmembrane nanopores. This counterintuitive hydrophobic effect resulted in some highly unusual transport behavior. Cholesterol normally increases the hydrophobicity of lipid membranes and makes them less permeable to hydrophilic molecules. The permeability of glucose across the oligocholate-containing membranes, however, increased significantly upon the inclusion of cholesterol. Large hydrophilic molecules tend to have difficulty traversing a hydrophobic barrier. The cyclic cholate tetramer, however, was more effective at permeating maltotriose than glucose.

  DOI：

  10.1021/ja109036z
• 作为产物：
  描述：

  在 甲醇 、 三苯基膦 作用下， 反应 4.0h， 以88%的产率得到
  参考文献：
  名称：

  Water-Templated Transmembrane Nanopores from Shape-Persistent Oligocholate Macrocycles

  摘要：

  Hydrophobic interactions normally are not considered a major driving force for self-assembling in a hydrophobic environment. When macrocyclic oligocholates were placed within lipid membranes, however, the macrocycles pulled water molecules from the aqueous phase into their hydrophilic internal cavities. These water molecules had strong tendencies to aggregate in a hydrophobic environment and templated the macrocycles to self-assemble into transmembrane nanopores. This counterintuitive hydrophobic effect resulted in some highly unusual transport behavior. Cholesterol normally increases the hydrophobicity of lipid membranes and makes them less permeable to hydrophilic molecules. The permeability of glucose across the oligocholate-containing membranes, however, increased significantly upon the inclusion of cholesterol. Large hydrophilic molecules tend to have difficulty traversing a hydrophobic barrier. The cyclic cholate tetramer, however, was more effective at permeating maltotriose than glucose.

  DOI：

  10.1021/ja109036z

文献信息

• Efficient Construction of Oligocholate Foldamers via “Click” Chemistry and Their Tolerance of Structural Heterogeneity
  作者：Xingang Pan、Yan Zhao

  DOI：10.1021/ol802364c

  日期：2009.1.1

  The 1,3-dipolar cycloaddition between an alkynyl-terminated cholate trimer and an azido-functionalized cholate hexamer readily afforded the nonamer and dodecamer derivatives; whereas amide coupling employed in previous oligocholate synthesis failed beyond the octamer. Unlike typical oligocholate foldamers with exclusively head-to-tall arrangement of the repeat units, the newly synthesized "clicked" oligocholates contained head-to-head arrangement and flexible tethers in the sequence. Despite large structural perturbations, the clicked oligocholates folded similarly as the parent foldamers, demonstrating the robustness of the solvophobically driven folding mechanism.
• Oligocholate foldamer with ‘prefolded’ macrocycles for enhanced folding in solution and surfactant micelles
  作者：Xueshu Li、Yan Zhao

  DOI：10.1016/j.tet.2013.05.088

  日期：2013.7

  A cholate oligomer was synthesized with six linear cholate groups sandwiched by two tricholate macrocycles at the two termini. Two pyrenyl labels on the compound allowed its conformation to be studied by fluorescence spectroscopy. The linear/macrocyclic hybrid oligomer was found to fold consistently better than a linear analogue in mixed organic solvents and surfactant micelles. The enhanced folding was hypothesized to occur as the tricholate macrocycles, by their prefolded configuration, facilitate the preferential salvation of the facially amphiphilic cholate groups. In general, the folding-enhancing effect was stronger as the environment became more challenging for the oligocholate to fold. Most unusually, the hybrid oligocholate folded better in a more challenging binary methanol/ethyl acetate mixture than in the methanol/hexane/ethyl acetate ternary solvents that have been considered the most 'folding-friendly' to all other cholate foldamers. (C) 2013 Elsevier Ltd. All rights reserved.