¹⁵N-dioleoylphosphatidylcholine | 1428647-94-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: ¹⁵N-dioleoylphosphatidylcholine
• 英文别名: ¹⁵N-DOPC
• CAS: 1428647-94-2
• 化学式: C₄₄H₈₄NO₈P
• 分子量: 787.12
• InChiKey: SNKAWJBJQDLSFF-RQERDXDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.72
• 重原子数：
  54.0
• 可旋转键数：
  40.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  111.19
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  氯化胆碱-¹⁵N 、 1,2-dioleoyl-sn-glycero-3-phosphate 在 吡啶 、 三氯乙腈 作用下， 以32.2%的产率得到¹⁵N-dioleoylphosphatidylcholine
  参考文献：
  名称：

  Colocalization of the Ganglioside G_M1 and Cholesterol Detected by Secondary Ion Mass Spectrometry

  摘要：

  The characterization of the lateral organization of components in biological membranes and the evolution of this arrangement in response to external triggers remain a major challenge. The concept of lipid rafts is widely invoked; however, direct evidence of the existence of these ephemeral entities remains elusive. We report here the use of secondary ion mass spectrometry (SIMS) to image the cholesterol-dependent cohesive phase separation of the ganglioside G(M1) into nano- and microscale assemblies in a canonical lipid raft composition of lipids. This assembly of domains was interrogated in a model membrane system composed of palmitoyl sphingomyelin (PSM), cholesterol, and an unsaturated lipid (dioleoylphosphatidylcholine, DOPC). Orthogonal isotopic labeling of every lipid bilayer component and monofluorination of G(M1) allowed generation of molecule specific images using a NanoSIMS. Simultaneous detection of six different ion species in SIMS, including secondary electrons, was used to generate ion ratio images whose signal intensity values could be correlated to composition through the use of calibration curves from standard samples. Images of this system provide the first direct, molecule specific, visual evidence for the colocalization of cholesterol and G(M1) in supported lipid bilayers and further indicate the presence of three compositionally distinct phases: (1) the interdomain region; (2) micrometer-scale domains (d > 3 mu m); (3) nanometer-scale domains (d = 100 nm to 1 mu m) localized within the micrometer-scale domains and the interdomain region. PSM-rich, nanometer-scale domains prefer to partition within the more ordered, cholesterol-rich/DOPC-poor/G(M1)-rich micrometer-scale phase, while G(M1)-rich, nanometer-scale domains prefer to partition within the surrounding, disordered, cholesterol-poor/PSM-rich/DOPC-rich interdomain phase.

  DOI：

  10.1021/ja310831m