1-O-10,11',14'-(Z,Z,Z)-icosatrienyl-2-hydroxy-sn-glycero-3-phosphoethanolamine | 1609562-85-7

• 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: 1-O-10,11',14'-(Z,Z,Z)-icosatrienyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
• 英文别名: 2-aminoethyl [(2R)-2-hydroxy-3-[(1Z,11Z,14Z)-icosa-1,11,14-trienoxy]propyl] hydrogen phosphate
• CAS: 1609562-85-7
• 化学式: C₂₅H₄₈NO₆P
• 分子量: 489.633
• InChiKey: ILSXASCRPNLHSC-GPJZPEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-O-(1',2'-dichloroethenyl)-sn-glycerol 在 吡啶 、 咪唑 、 喹啉 、 4-二甲氨基吡啶 、 正丁基锂 、 rosenmund catalyst 、 氢气 、 氟化氢吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1-O-10,11',14'-(Z,Z,Z)-icosatrienyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
  参考文献：
  名称：

  Synthesis and evaluation of immunostimulant plasmalogen lysophosphatidylethanolamine and analogues for natural killer T cells

  摘要：

  Plasmalogen lysophosphatidylethanolamine (pLPE) had been identified as a self antigen for natural killer T cells (NKT cells). It is very important in the development, maturation and activation of NKT cells in thymus. Besides, pLPE is a novel type of antigen for NKT cells. To evaluate the structure-activity relationship (SAR) of this new antigen, pLPE and its analogues referred to different aliphatic chains and linkages at the sn-1 position of the glycerol backbone were synthesized, and the biological activities of these analogues was characterized. It is discovered that the linkages between phosphate and lipid moiety are not important for the antigens' activities. The pLPE analogues 1, 3, 4, 7 and 9, which have additional double bonds on lipid parts, were identified as new NKT agonists. Moreover, the analogues 4, 7 and 9 were discovered as potent Th2 activators for NKT cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.012

文献信息

• Synthesis and evaluation of immunostimulant plasmalogen lysophosphatidylethanolamine and analogues for natural killer T cells
  作者：Guanghui Ni、Zhiyuan Li、Kangjiang Liang、Ting Wu、Gennaro De Libero、Chengfeng Xia

  DOI：10.1016/j.bmc.2014.04.012

  日期：2014.6

  Plasmalogen lysophosphatidylethanolamine (pLPE) had been identified as a self antigen for natural killer T cells (NKT cells). It is very important in the development, maturation and activation of NKT cells in thymus. Besides, pLPE is a novel type of antigen for NKT cells. To evaluate the structure-activity relationship (SAR) of this new antigen, pLPE and its analogues referred to different aliphatic chains and linkages at the sn-1 position of the glycerol backbone were synthesized, and the biological activities of these analogues was characterized. It is discovered that the linkages between phosphate and lipid moiety are not important for the antigens' activities. The pLPE analogues 1, 3, 4, 7 and 9, which have additional double bonds on lipid parts, were identified as new NKT agonists. Moreover, the analogues 4, 7 and 9 were discovered as potent Th2 activators for NKT cells. (C) 2014 Elsevier Ltd. All rights reserved.