| 1174764-25-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• CAS: 1174764-25-0
• 化学式: C₅₄H₁₀₄NO₉PS₃
• 分子量: 1038.59
• InChiKey: BYLCYUBPXWBISL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  68.0
• 可旋转键数：
  51.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  137.46
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  1,2-二棕榈酰-外消旋-甘油-3-磷酰乙醇胺 、 S-dodecyl-S'-(α,α-dimethylpentafluorophenyl acetate)trithiocarbonate 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.0h， 以71%的产率得到
  参考文献：
  名称：

  Control of the Molecular Orientation of Membrane-Anchored Biomimetic Glycopolymers

  摘要：

  Quantifying and controlling the orientation of surface-bound macromolecules is crucial to a wide range of processes in areas as diverse as biology, materials science, and nanotechnology. Methods capable of directing orientation, as well as an understanding of the underlying physical mechanisms are, however, lacking. In this paper, we describe experiments in which the conformations of structurally well-defined polymers anchored to fluid lipid membranes were probed using Fluorescence Interference Contrast Microscopy (FLIC), an optical technique that provides topographic information with few-nanometer precision. The novel rodlike polymers mimic the architecture of mucin glycoproteins and feature a phospholipid tail for membrane incorporation and a fluorescent optical probe for FLIC imaging situated at the opposite termini of the densely glycosylated polymeric backbones. We find that the orientation of the rigid, approximately 30 nm long glycopolymers depends profoundly on the properties of the optical reporter. Molecules terminated with Alexa Fluor 488 projected away from the lipid bilayer by 11 +/- 1 nm, consistent with entropy-dominated sampling of the membrane-proximal space. Molecules terminated with Texas Red lie flat at the membrane (height, 0 +/- 2 nm), implying that interactions between Texas Red and the bilayer dominate the polymers' free energy. These results demonstrate the design of macromolecules with specific orientational preferences, as well as nanometer-scale measurement of their orientation. Importantly, they reveal that seemingly minute changes in molecular structure, in this case fluorophores that comprise only 2% of the total molecular weight, can significantly alter the molecule's presentation to the surrounding environment.

  DOI：

  10.1021/ja903114g