(R)-2-hydroxy-3-(phosphonooxy)propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

• 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: (R)-2-hydroxy-3-(phosphonooxy)propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• 英文别名: 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycero-3-phosphate；[(2R)-2-hydroxy-3-phosphonooxypropyl] (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• 化学式: C₂₅H₃₉O₇P
• 分子量: 482.554
• InChiKey: UWHSPTWBPTXYMF-DOYOFOADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2-didocosahexaenoyl-sn-glycero-3-phosphate 在 phospholipase A₂ 作用下， 以 aq. buffer 为溶剂， 反应 16.0h， 生成 (R)-2-hydroxy-3-(phosphonooxy)propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
  参考文献：
  名称：

  Challenges in accurate quantitation of lysophosphatidic acids in human biofluids

  摘要：

  Lysophosphatidic acids (LPAs) are biologically active signaling molecules involved in the regulation of many cellular processes and have been implicated as potential mediators of fibroblast recruitment to the pulmonary airspace, pointing to possible involvement of LPA in the pathology of pulmonary fibrosis. LPAs have been measured in various biological matrices and many challenges involved with their analyses have been documented. However, little published information is available describing LPA levels in human bronchoalveolar lavage fluid (BALF). We therefore conducted detailed investigations into the effects of extensive sample handling and sample preparation conditions on LPA levels in human BALF. Further, targeted lipid profiling of human BALF and plasma identified the most abundant lysophospholipids likely to interfere with LPA measurements. We present the findings from these investigations, highlighting the importance of well-controlled sample handling for the accurate quantitation of LPA. Further, we show that chromatographic separation of individual LPA species from their corresponding lysophospholipid species is critical to avoid reporting artificially elevated levels. The optimized sample preparation and LC/MS/MS method was qualified using a stable isotope-labeled LPA as a surrogate calibrant and used to determine LPA levels in human BALF and plasma from a Phase 0 clinical study comparing idiopathic pulmonary fibrosis patients to healthy controls.

  DOI：

  10.1194/jlr.d050070

文献信息

• A study of synthetic approaches to 2-acyl DHA lysophosphatidic acid
  作者：Yoshinori Yamamoto、Toshimasa Itoh、Keiko Yamamoto

  DOI：10.1039/c7ob01771e

  日期：——

  Lysophosphatidic acid (LPA) is a chemical mediator with a very simple glycerophospholipid structure. 1-acyl LPA and 2-acyl LPA are biosynthesized in vivo. Unlike 1-acyl LPA, the biological function of 2-acyl LPA has been hardly elucidated and even organic synthesis of 2-acyl LPA had not been established.　We suppressed acyl migration by formation of a salt with a phosphate group in order to synthesize

  溶血磷脂酸（LPA）是具有非常简单的甘油磷脂结构的化学介质。1-酰基LPA和2-酰基LPA是在体内生物合成的。与1-酰基LPA不同，几乎没有阐明2-酰基LPA的生物学功能，甚至还没有建立2-酰基LPA的有机合成。为了合成与二十二碳六烯酸缩合的2-酰基LPA，我们通过形成具有磷酸基的盐来抑制酰基的迁移。