1-O-dimethoxyphosphoryl-2-O-oleoyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol | 637774-52-8

• 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: 1-O-dimethoxyphosphoryl-2-O-oleoyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
• 英文别名: 3-O-dimethylphosphoryl-(2R)-O-oleoyl-1-O-(tetrahydro-pyran-2-yloxy)ethyl-sn-glycerol
• CAS: 637774-52-8
• 化学式: C₃₀H₅₇O₉P
• 分子量: 592.751
• InChiKey: CLQNNGDBGBNUDZ-HQZRXGBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  40.0
• 可旋转键数：
  27.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-O-dimethoxyphosphoryl-2-O-oleoyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol 在 三甲基溴硅烷 、 水 作用下， 以 甲醇 为溶剂， 生成
  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：

  2-O-tert-butyldimethylsilyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol 在 N-甲基咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-O-dimethoxyphosphoryl-2-O-oleoyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
  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

• [EN] ANALOGS OF LYSOPHOSPHATIDIC ACID AND METHODS OF MAKING AND USING THEREOF<br/>[FR] ANALOGUES D'ACIDE LYSOPHOSPHATIDIQUE ET PROCEDES DE LEUR FABRICATION ET DE LEUR UTILISATION
  申请人：UNIV UTAH RES FOUND

  公开号：WO2004092188A3

  公开（公告）日：2005-04-28