[3-[(Z)-hexadec-9-enoxy]-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | 93135-88-7

• 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: [3-[(Z)-hexadec-9-enoxy]-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 93135-88-7
• 化学式: C₂₄H₅₀NO₆P
• 分子量: 479.638
• InChiKey: PLQWZMJRHVARFU-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [3-[(Z)-hexadec-9-enoxy]-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以36%的产率得到PC(O-16:1(9Z)/2:0)[U]
  参考文献：
  名称：

  Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain

  摘要：

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.

  DOI：

  10.1021/jm00379a015
• 作为产物：
  描述：

  甲苯磺酸胆碱 在 吡啶 、 三乙胺 、 zinc dibromide 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 29.5h， 生成 [3-[(Z)-hexadec-9-enoxy]-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
  参考文献：
  名称：

  Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain

  摘要：

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.

  DOI：

  10.1021/jm00379a015

文献信息

• Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain
  作者：Jefferson R. Surles、Robert L. Wykle、Joseph T. O'Flaherty、William L. Salzer、Michael J. Thomas、Fred Snyder、Claude Piantadosi

  DOI：10.1021/jm00379a015

  日期：1985.1

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.