3-(((2-aminoethoxy)(hydroxy)phosphoryl)oxy)-2-hydroxypropyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate | 120282-75-9

• 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-(((2-aminoethoxy)(hydroxy)phosphoryl)oxy)-2-hydroxypropyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 120282-75-9
• 化学式: C₂₅H₄₄NO₇P
• 分子量: 501.601
• InChiKey: ROPRRXYVXLDXQO-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  34.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  128.31
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以37%的产率得到3-(((2-aminoethoxy)(hydroxy)phosphoryl)oxy)-2-hydroxypropyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
  参考文献：
  名称：

  Rapid tin-mediated access to a lysophosphatidylethanolamine (LPE) library: Application to positional LC/MS analysis for hepatic LPEs in non-alcoholic steatohepatitis model mice

  摘要：

  Even though lysophospholipids have attracted much interest in recent years on account of their unique bioactivity, research related to lysophospholipids is usually hampered by problems associated with standard sample preparation and discrimination of regioisomers. Herein, we demonstrate a quick tin chemistry-based synthetic route to lysophosphatidylethanolamines (LPEs) and its application in the positional analysis of hepatic LPEs in non-alcoholic steatohepatitis (NASH) model mice. We found that the preference of hepatic LPE regioisomer largely depends on the unsaturation of acyl chain in both control and NASH model mice. In addition, hepatic C18:2-LPE and C20:5-LPE levels were significantly lower in the NASH model mice than those in the control. The LC/MS technique based on the library of LPE regioisomers allows an accurate observation of hepatic LPE metabolism and might provide useful information to elucidate yet ambiguous pathogenesis of NASH. (C) 2016 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2016.09.003

文献信息

• Rapid tin-mediated access to a lysophosphatidylethanolamine (LPE) library: Application to positional LC/MS analysis for hepatic LPEs in non-alcoholic steatohepatitis model mice
  作者：Takayuki Furukawa、Hirotoshi Fuda、Satoshi Miyanaga、Chinatsu Watanabe、Hitoshi Chiba、Shu-Ping Hui

  DOI：10.1016/j.chemphyslip.2016.09.003

  日期：2016.10

  Even though lysophospholipids have attracted much interest in recent years on account of their unique bioactivity, research related to lysophospholipids is usually hampered by problems associated with standard sample preparation and discrimination of regioisomers. Herein, we demonstrate a quick tin chemistry-based synthetic route to lysophosphatidylethanolamines (LPEs) and its application in the positional analysis of hepatic LPEs in non-alcoholic steatohepatitis (NASH) model mice. We found that the preference of hepatic LPE regioisomer largely depends on the unsaturation of acyl chain in both control and NASH model mice. In addition, hepatic C18:2-LPE and C20:5-LPE levels were significantly lower in the NASH model mice than those in the control. The LC/MS technique based on the library of LPE regioisomers allows an accurate observation of hepatic LPE metabolism and might provide useful information to elucidate yet ambiguous pathogenesis of NASH. (C) 2016 Elsevier Ireland Ltd. All rights reserved.