1-myristoyl-2-hydroxy-sn-glycero-3-phosphoethanoalmine

• 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: 1-myristoyl-2-hydroxy-sn-glycero-3-phosphoethanoalmine
• 英文别名: [(2S)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] tetradecanoate
• 化学式: C₁₉H₄₀NO₇P
• 分子量: 425.503
• InChiKey: RPXHXZNGZBHSMJ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 1-myristoyl-2-hydroxy-sn-glycero-3-phosphoethanoalmine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 以95%的产率得到Tetradecanoic acid (S)-3-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-2-hydroxy-propyl ester
  参考文献：
  名称：

  Synthesis and Properties of a Bipolar, Bisphosphatidyl Ethanolamine That Forms Stable 2-Dimensional Self-Assembled Bilayer Systems and Liposomes

  摘要：

  Phosphatidyl ethanolamine is one of the most common naturally occurring phospholipids. The presence of an amino group also makes it one of the most straightforward to functionalize. Unfortunately however, it tends to form micelles and hexagonal clusters instead of forming lamellar systems such as sheets and vesicles (liposomes), key supramolecular structures for a variety of biomedical and other technical applications. This has been overcome by synthesizing a dimeric phosphatidyl ethanolamine molecule in which the acyl chains at the 2-position of glycerol are joined at their termini by a carbon-carbon bond, thus resulting in a trans-membrane type fatty acyl linkage. Such tail-to-tail bipolar transmembrane lipids are found in the membranes of thermophilic and other extremophilic bacteria. The dimeric phosphatidyl ethanolamine readily forms very uniformly flat self-assembled lamellar supramolecular arrays and liposomes that are stable at temperatures up to 80 degrees C. The planar systems formed by the new lipid were characterized by atomic force microscopy, and the uniformity of the vesicles was observed by laser scanning confocal microscopy, The thermal stability of the phospholipid and the vesicles formed was examined by NMR spectroscopy including proton T-1 measurements as a function of temperature. Fourier transform infrared spectroscopy indicated a much greater order of the alkyl chain in the dimer than in phosphatidyl ethanolamine. This extremely stable and readily functionalizable dimeric phospholipid has potential uses in the fabrication of biomaterials, stable membrane models, and liposome drug-delivery systems.

  DOI：

  10.1021/jo9902852

文献信息

• Synthesis and Properties of a Bipolar, Bisphosphatidyl Ethanolamine That Forms Stable 2-Dimensional Self-Assembled Bilayer Systems and Liposomes
  作者：Guijun Wang、Rawle I. Hollingsworth

  DOI：10.1021/jo9902852

  日期：1999.5.1

  Phosphatidyl ethanolamine is one of the most common naturally occurring phospholipids. The presence of an amino group also makes it one of the most straightforward to functionalize. Unfortunately however, it tends to form micelles and hexagonal clusters instead of forming lamellar systems such as sheets and vesicles (liposomes), key supramolecular structures for a variety of biomedical and other technical applications. This has been overcome by synthesizing a dimeric phosphatidyl ethanolamine molecule in which the acyl chains at the 2-position of glycerol are joined at their termini by a carbon-carbon bond, thus resulting in a trans-membrane type fatty acyl linkage. Such tail-to-tail bipolar transmembrane lipids are found in the membranes of thermophilic and other extremophilic bacteria. The dimeric phosphatidyl ethanolamine readily forms very uniformly flat self-assembled lamellar supramolecular arrays and liposomes that are stable at temperatures up to 80 degrees C. The planar systems formed by the new lipid were characterized by atomic force microscopy, and the uniformity of the vesicles was observed by laser scanning confocal microscopy, The thermal stability of the phospholipid and the vesicles formed was examined by NMR spectroscopy including proton T-1 measurements as a function of temperature. Fourier transform infrared spectroscopy indicated a much greater order of the alkyl chain in the dimer than in phosphatidyl ethanolamine. This extremely stable and readily functionalizable dimeric phospholipid has potential uses in the fabrication of biomaterials, stable membrane models, and liposome drug-delivery systems.