S-arachidonoyl 2-thioglycerol | 1226498-86-7

• 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: S-arachidonoyl 2-thioglycerol
• CAS: 1226498-86-7
• 化学式: C₂₃H₃₈O₃S
• 分子量: 394.619
• InChiKey: FUPPZPCZQZGIBJ-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  27.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  S-arachidonoyl 2-thioglycerol 在 human recombinant monoacylglycerol lipase 作用下， 以 aq. Tris buffer 为溶剂， 生成 2-mercapto-1,3-propanediol
  参考文献：
  名称：

  S-Arachidonoyl-2-thioglycerol synthesis and use for fluorimetric and colorimetric assays of monoacylglycerol lipase

  摘要：

  We report the first synthesis of 2-thioglycerol and S-arachidonoyl-2-thioglycerol (the thioester analog of the endocannabinoid 2-arachidonoylglycerol) in an eight or nine step procedure with a yield of similar to 25% and establish the use of this substrate for maleimide-based fluorescent and dithiobis(2-nitrobenzoic acid)-based colorimetric assays of human recombinant monoacylglycerol (MAG) lipase (hMAGL) and human brain membrane MAG hydrolase activity. Inhibitor structure-activity relationships observed here for hMAGL and 2-ATG correlate well (r(2) = 0.93, n = 9) with earlier findings for mouse brain MAG hydrolase with non-thiol substrates. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.034
• 作为产物：
  描述：

  花生四烯酰氯 、 2-mercapto-1,3-propanediol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80 mg的产率得到S-arachidonoyl 2-thioglycerol
  参考文献：
  名称：

  S-Arachidonoyl-2-thioglycerol synthesis and use for fluorimetric and colorimetric assays of monoacylglycerol lipase

  摘要：

  We report the first synthesis of 2-thioglycerol and S-arachidonoyl-2-thioglycerol (the thioester analog of the endocannabinoid 2-arachidonoylglycerol) in an eight or nine step procedure with a yield of similar to 25% and establish the use of this substrate for maleimide-based fluorescent and dithiobis(2-nitrobenzoic acid)-based colorimetric assays of human recombinant monoacylglycerol (MAG) lipase (hMAGL) and human brain membrane MAG hydrolase activity. Inhibitor structure-activity relationships observed here for hMAGL and 2-ATG correlate well (r(2) = 0.93, n = 9) with earlier findings for mouse brain MAG hydrolase with non-thiol substrates. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.034