1,2-α-eleostearoyl-sn-glycero-3-phosphocholine

• 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: 1,2-α-eleostearoyl-sn-glycero-3-phosphocholine
• 英文别名: 1,2-dielaeostearoyl-sn-glycero-3-phophatidylcholine；1,2-di-(9Z,11E,13E-octadecatrienoyl)-sn-glycero-3-phosphocholine；[(2R)-2,3-bis[[(9Z,11E,13E)-octadeca-9,11,13-trienoyl]oxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
• 化学式: C₄₄H₇₆NO₈P
• 分子量: 778.063
• InChiKey: GQJQPGHLMIZLHW-ZUCHIBDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  54
• 可旋转键数：
  38
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  alpha-桐酸 、 甘磷酸胆碱 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以77%的产率得到1,2-α-eleostearoyl-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Development of a High-Throughput Assay for Measuring Phospholipase A Activity Using Synthetic 1,2-α-Eleostearoyl-sn-glycero-3-phosphocholine Coated on Microtiter Plates

  摘要：

  迄今为止，基于放射性标记元素或空间位阻氟硼荧光素基团的多种敏感方法通常被用于筛选磷脂酶A（PLA）活性。为了开发一种方便、特异、敏感且可连续进行的新型紫外（UV）分光光度法PLA检测方法，我们合成了一种在sn-1和sn-2位置上酯化有从油桐（Aleurites fordii）种子油中纯化的α-桐酸（9Z,11E,13E-十八碳三烯酸）的特定甘油磷脂酰胆碱（PC）。α-桐酸中存在的共轭三烯构成了一种固有的发色团，因此赋予了这种游离脂肪酸及其包含的甘油磷脂强大的紫外吸收特性。这种涂覆的PC膜在PLA检测过程中无法被各种缓冲液解吸。在油水界面经过PLA作用后，α-桐酸被释放并从膜中解吸，然后与β-环糊精溶解。由于从吸附状态转变为水溶性状态，α-桐酸的紫外吸光度显著增强。通过记录紫外吸收光谱随时间的变化，可以连续测量PLA活性。通过测量272 nm处吸收增加的情况来监测脂解速率，发现其随时间呈线性且与添加的PLA量成正比。这种连续的高通量PLA检测方法可用于筛选存在于各种生物样本中的新型PLA和/或PLA抑制剂。

  DOI：

  10.1021/ac502096v

文献信息

• Effects of molecular structures on the olfactory responses of phospholipid membranes to four alcohols
  作者：Qingzhong Zhou、Yanan Yang、Zhikuan Chen、Anna Sun

  DOI：10.1016/s0009-3084(98)00054-1

  日期：1998.9

  In order to understand the relationship between phospholipid molecular structures and their olfactory responses to odorants, we designed and synthesized four phosphatidylcholine analogues with different long hydrocarbon (CH) chains and selected three natural phospholipids with different head-groups. By using interdigital electrodes (IEs) as olfactory sensors (OSs), we measured the responses of the Ifs coated with these seven different lipid membranes to four alcohol vapors in a gas flow system. The Ifs voltage changes were recorded and the voltage-relative saturate vapor pressure (V-P/P degrees) curves were also plotted. It was found that with a methyl (-CH3) placed at the C-8 position in the 18-carbon chain, the olfactory responses could be improved about ten times and with conjugated double bonds (C=C) in the long chains, the sensitivity could be increased by 3 similar to 4 orders of magnitude. As to head-groups, choline is preferred over ethanolamine and serine in phospholipid structures in terms of high olfactory sensitivity: These results are expected to be useful in further designing and manufacturing lipid-mimicking OSs. (C) 1998 Elsevier Science Ireland Ltd. All rights reserved.
• Development of a High-Throughput Assay for Measuring Phospholipase A Activity Using Synthetic 1,2-α-Eleostearoyl-<i>sn</i>-glycero-3-phosphocholine Coated on Microtiter Plates
  作者：Meddy El Alaoui、Alexandre Noiriel、Laurent Soulère、Lucie Grand、Yves Queneau、Abdelkarim Abousalham

  DOI：10.1021/ac502096v

  日期：2014.11.4

  To date, several sensitive methods, based on radiolabeled elements or sterically hindered fluorochrome groups, are usually employed to screen phospholipase A (PLA) activities. With the aim of developing a convenient, specific, sensitive, and continuous new ultraviolet (UV) spectrophotometric assay for PLA, we have synthesized a specific glycerophosphatidylcholine (PC) esterified at the sn-1 and sn-2 positions, with α-eleostearic acid (9Z, 11E, 13E-octadecatrienoic acid) purified from Aleurites fordii seed oil. The conjugated triene present in α-eleostearic acid constitutes an intrinsic chromophore and, consequently, confers the strong UV absorption properties of this free fatty acid as well as of the glycerophospholipids harboring it. This coated PC film cannot be desorbed by the various buffers used during PLA assays. Following the action of PLA at the oil–water interface, α-eleostearic acid is freed and desorbed from the film and then solubilized with β-cyclodextrin. The UV absorbance of the α-eleostearic acid is considerably enhanced due to the transformation from an adsorbed to a water-soluble state. The PLA activity can be measured continuously by recording the variations with time of the UV absorption spectra. The rate of lipolysis was monitored by measuring the increase of absorption at 272 nm, which was found to be linear with time and proportional to the amount of added PLA. This continuous high-throughput PLA assay could be used to screen new PLA and/or PLA inhibitors present in various biological samples.

  迄今为止，基于放射性标记元素或空间位阻氟硼荧光素基团的多种敏感方法通常被用于筛选磷脂酶A（PLA）活性。为了开发一种方便、特异、敏感且可连续进行的新型紫外（UV）分光光度法PLA检测方法，我们合成了一种在sn-1和sn-2位置上酯化有从油桐（Aleurites fordii）种子油中纯化的α-桐酸（9Z,11E,13E-十八碳三烯酸）的特定甘油磷脂酰胆碱（PC）。α-桐酸中存在的共轭三烯构成了一种固有的发色团，因此赋予了这种游离脂肪酸及其包含的甘油磷脂强大的紫外吸收特性。这种涂覆的PC膜在PLA检测过程中无法被各种缓冲液解吸。在油水界面经过PLA作用后，α-桐酸被释放并从膜中解吸，然后与β-环糊精溶解。由于从吸附状态转变为水溶性状态，α-桐酸的紫外吸光度显著增强。通过记录紫外吸收光谱随时间的变化，可以连续测量PLA活性。通过测量272 nm处吸收增加的情况来监测脂解速率，发现其随时间呈线性且与添加的PLA量成正比。这种连续的高通量PLA检测方法可用于筛选存在于各种生物样本中的新型PLA和/或PLA抑制剂。