[(2S)-3-[dimethoxy(oxido)phosphaniumyl]oxy-2-[2-(oxan-2-yloxy)ethoxy]propyl] hexadecanoate | 637774-44-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2S)-3-[dimethoxy(oxido)phosphaniumyl]oxy-2-[2-(oxan-2-yloxy)ethoxy]propyl] hexadecanoate
• CAS: 637774-44-8
• 化学式: C₂₈H₅₅O₉P
• 分子量: 566.713
• InChiKey: JSVLQLRZNYEAOI-QODXOHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  38
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2S)-3-[dimethoxy(oxido)phosphaniumyl]oxy-2-[2-(oxan-2-yloxy)ethoxy]propyl] hexadecanoate 在 三甲基溴硅烷 、 水 作用下， 以 甲醇 为溶剂， 生成 Hexadecanoic acid (S)-2-(2-hydroxy-ethoxy)-3-phosphonooxy-propyl ester
  参考文献：
  名称：

  Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

  摘要：

  The susceptibility of lysophosphatidic acid (LPA) to intramolecular acyl migration impedes the determination of specific receptor activation by the sn-1 and sn-2 LPA regioisomers. An efficient enantioselective synthesis of hydroxyethoxy (HE)-substituted analogues of sn-1-acyl and 2-acyl LPA derivatives that possess palmitoyl and oleoyl chains is described. While the palmitoyl derivatives fall to activate calcium release in cells transfected with LPA(2) or LPA(3) G-protein-coupled receptors, the LPA(3) receptor is activated by both 1-HE and 2-HE oleoyl LPA analogues with a potency 10-fold lower than that of the parent oleoyl LPA.

  DOI：

  10.1021/ol0358758
• 作为产物：
  描述：

  1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S)-3-[dimethoxy(oxido)phosphaniumyl]oxy-2-[2-(oxan-2-yloxy)ethoxy]propyl] hexadecanoate
  参考文献：
  名称：

  Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

  摘要：

  The susceptibility of lysophosphatidic acid (LPA) to intramolecular acyl migration impedes the determination of specific receptor activation by the sn-1 and sn-2 LPA regioisomers. An efficient enantioselective synthesis of hydroxyethoxy (HE)-substituted analogues of sn-1-acyl and 2-acyl LPA derivatives that possess palmitoyl and oleoyl chains is described. While the palmitoyl derivatives fall to activate calcium release in cells transfected with LPA(2) or LPA(3) G-protein-coupled receptors, the LPA(3) receptor is activated by both 1-HE and 2-HE oleoyl LPA analogues with a potency 10-fold lower than that of the parent oleoyl LPA.

  DOI：

  10.1021/ol0358758

文献信息

• Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid
  作者：Lian Qian、Yong Xu、Hiroyuki Arai、Junken Aoki、Thomas M. McIntyre、Glenn D. Prestwich

  DOI：10.1021/ol0358758

  日期：2003.11.1

  The susceptibility of lysophosphatidic acid (LPA) to intramolecular acyl migration impedes the determination of specific receptor activation by the sn-1 and sn-2 LPA regioisomers. An efficient enantioselective synthesis of hydroxyethoxy (HE)-substituted analogues of sn-1-acyl and 2-acyl LPA derivatives that possess palmitoyl and oleoyl chains is described. While the palmitoyl derivatives fall to activate calcium release in cells transfected with LPA(2) or LPA(3) G-protein-coupled receptors, the LPA(3) receptor is activated by both 1-HE and 2-HE oleoyl LPA analogues with a potency 10-fold lower than that of the parent oleoyl LPA.