| 1019646-75-3

• 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: 1019646-75-3
• 化学式: C₂₇H₄₅FO
• 分子量: 405.644
• InChiKey: KVAZIFKRVOEFIV-NBRADJPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  在 硼氘化钠 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 以34%的产率得到
  参考文献：
  名称：

  Orientation of Fluorinated Cholesterol in Lipid Bilayers Analyzed by ¹⁹F Tensor Calculation and Solid-State NMR

  摘要：

  6-F-cholesterol was reported to exhibit biological and interfacial properties similar to unmodified cholesterol. We have also found that 6-F-cholesterol mimicked the cholesterol activity observed in the systems of amphotericin B and lipid rafts. However, to use 6-F-cholesterol as a molecular probe to explore molecular recognition in membranes, it is indispensable to have detailed knowledge of the dynamic and orientation properties of the molecule in membrane environments. In this paper, we present the molecular orientation of 6-F-cholesterol (30 mol %) in dimyristoylphosphatidylcholine (DMPC) bilayers revealed by combined use of F-19 chemical shift anisotropy (CSA), H-2 NMR, and C-F rotational echo double resonance (REDOR) experiments. The axis of rotation of 6-F-cholesterol was shown to be in a similar direction to that of cholesterol in DMPC bilayers, which is almost parallel to the long axis of the molecular frame. The molecular order parameter of 6-F-cholesterol was determined to be ca. 0.85, which is within the range of reported values of cholesterol. These findings suggest that the dynamic properties of 6-F-cholesterol in DMPC are quite similar to those of unmodified cholesterol; therefore, the introduction of a fluorine atom at C6 has virtually no effect on cholesterol dynamics in membranes. In addition, this study demonstrates the practical utility of theoretical calculations for determining the F-19 CSA principal axes, which would be extremely difficult to obtain experimentally. The combined use of quantum calculations and solid-state F-19 NMR will make it possible to apply the orientation information of F-19 CSA tensors to membrane systems.

  DOI：

  10.1021/ja077580l