Octadecanoic acid (R)-2-({2-[3-(4-tert-butoxycarbonylamino-phenyl)-3-methyl-ureido]-ethoxy}-hydroxy-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester | 173912-50-0

• 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: Octadecanoic acid (R)-2-({2-[3-(4-tert-butoxycarbonylamino-phenyl)-3-methyl-ureido]-ethoxy}-hydroxy-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester
• 英文别名: [(2R)-3-[hydroxy-[2-[[methyl-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]carbamoyl]amino]ethoxy]phosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate
• CAS: 173912-50-0
• 化学式: C₅₄H₉₈N₃O₁₁P
• 分子量: 996.359
• InChiKey: ATBYTLHBGUPDBA-ANFMRNGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  69
• 可旋转键数：
  48
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  179
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 Octadecanoic acid (R)-2-({2-[3-(4-tert-butoxycarbonylamino-phenyl)-3-methyl-ureido]-ethoxy}-hydroxy-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester 在 sodium nitrite 作用下， 生成 4-(3-<2-<((2,3-bis(octadecanoyloxy)propoxy)hydroxyphosphoryl)oxy>ethyl>-1-methylureido)benzenediazonium trifluoroacetate
  参考文献：
  名称：

  Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed To Probe the Membrane-Associate Domains of Proteins

  摘要：

  The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.

  DOI：

  10.1021/jo951350k
• 作为产物：
  描述：

  (2S)-3-羟基-1,2-丙烷二基二硬脂酸酯 在 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Octadecanoic acid (R)-2-({2-[3-(4-tert-butoxycarbonylamino-phenyl)-3-methyl-ureido]-ethoxy}-hydroxy-phosphoryloxy)-1-octadecanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed To Probe the Membrane-Associate Domains of Proteins

  摘要：

  The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.

  DOI：

  10.1021/jo951350k