2-hydroxy-1,3,2-dioxaborinan-5-yl (5'Z,8'Z,11'Z,14'Z)-icosa-5',8',11',14'-tetraenoate | 1274596-44-9

• 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: 2-hydroxy-1,3,2-dioxaborinan-5-yl (5'Z,8'Z,11'Z,14'Z)-icosa-5',8',11',14'-tetraenoate
• 英文别名: (2-hydroxy-1,3,2-dioxaborinan-5-yl) (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 1274596-44-9
• 化学式: C₂₃H₃₇BO₅
• 分子量: 404.355
• InChiKey: OSRZATOONNUCBT-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-花生酰基甘油 在 硼酸 作用下， 以 正己烷 、 水 、 乙酸乙酯 为溶剂， 生成 2-hydroxy-1,3,2-dioxaborinan-5-yl (5'Z,8'Z,11'Z,14'Z)-icosa-5',8',11',14'-tetraenoate
  参考文献：
  名称：

  A Methodology for Radiolabeling of the Endocannabinoid 2-Arachidonoylglycerol (2-AG)

  摘要：

  The metabolic intermediate and endocannabinoid signaling lipid 2-arachidonoylglycerol (2-AG) has not been readily labeled, primarily because of its instability toward rearrangement. We now detail a synthetic method that easily gives tritiated 2-AG from [5,6,8,9,11,12,14,15-H-3(N)]arachidonic acid in two steps. We utilized a short chain 1,3-diacylglycerol and proceeded through the "structured lipid" [5 '',6 '',8 '',9 '',11 '',12 '', 14 '',15 ''-H-3(N)]2-arachidonoyl-1,3-dibutyrylglycerol, a triacylglycerol that was conveniently deprotected in ethanol with acrylic beads containing Candida antarctica lipase B to give [5 '',6 '',8 '',9 '',11 '',12 '',14 '',15 ''-H-3(N)]2-arachidonoylglycerol ([H-3]2-AG). The flash chromatographic separation necessary to isolate the labeled 2'-acylglycerol [H-3]2-AG resulted in only 4% of the rearrangement byproducts that have been a particular problem with previous methodologies. This reliable "kit" method to prepare the radiolabeled endocannabinoid as needed gave tritiated 2-arachidonoylglycerol [H-3](2)-AG with a specific activity of 200 Ci/mmol for enzyme assays, metabolic studies, and tissue imaging. It has been run on unlabeled materials on over 10 mg scales and should be generally applicable to other 2-acylglycerols.

  DOI：

  10.1021/jo102277q

文献信息

• A Methodology for Radiolabeling of the Endocannabinoid 2-Arachidonoylglycerol (2-AG)
  作者：Richard I. Duclos、Meghan Johnston、Subramanian K. Vadivel、Alexandros Makriyannis、Sherrye T. Glaser、S. John Gatley

  DOI：10.1021/jo102277q

  日期：2011.4.1

  The metabolic intermediate and endocannabinoid signaling lipid 2-arachidonoylglycerol (2-AG) has not been readily labeled, primarily because of its instability toward rearrangement. We now detail a synthetic method that easily gives tritiated 2-AG from [5,6,8,9,11,12,14,15-H-3(N)]arachidonic acid in two steps. We utilized a short chain 1,3-diacylglycerol and proceeded through the "structured lipid" [5 '',6 '',8 '',9 '',11 '',12 '', 14 '',15 ''-H-3(N)]2-arachidonoyl-1,3-dibutyrylglycerol, a triacylglycerol that was conveniently deprotected in ethanol with acrylic beads containing Candida antarctica lipase B to give [5 '',6 '',8 '',9 '',11 '',12 '',14 '',15 ''-H-3(N)]2-arachidonoylglycerol ([H-3]2-AG). The flash chromatographic separation necessary to isolate the labeled 2'-acylglycerol [H-3]2-AG resulted in only 4% of the rearrangement byproducts that have been a particular problem with previous methodologies. This reliable "kit" method to prepare the radiolabeled endocannabinoid as needed gave tritiated 2-arachidonoylglycerol [H-3](2)-AG with a specific activity of 200 Ci/mmol for enzyme assays, metabolic studies, and tissue imaging. It has been run on unlabeled materials on over 10 mg scales and should be generally applicable to other 2-acylglycerols.