1-油酰基-2-羟基-sn-甘油-3-磷酸乙醇胺 | 89576-29-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 1-油酰基-2-羟基-sn-甘油-3-磷酸乙醇胺
• 中文别名: 溶血磷脂酰乙醇胺
• 英文名称: 1-oleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
• 英文别名: PE (18:1(9Z)/0:0)；1-18:1-lysoPE；2-azaniumylethyl [(2R)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropyl] phosphate
• CAS: 89576-29-4
• 化学式: C₂₃H₄₆NO₇P
• 分子量: 479.595
• InChiKey: PYVRVRFVLRNJLY-MZMPXXGTSA-N

物化性质

• 沸点：
  597.4±60.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：3 mg/ml
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  8

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

制备方法与用途

Oleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine是溴氰菊酯在体外被原核蛋白（如CYP6A14和CYP6N6）复合物主要代谢产生的降解产物。

反应信息

• 作为反应物：
  描述：

  1-油酰基-2-羟基-sn-甘油-3-磷酸乙醇胺 在 氨基-Α-环糊精 、 水 作用下， 以 aq. buffer 为溶剂， 反应 72.0h， 生成 油酸
  参考文献：
  名称：

  Lipase mimetic cyclodextrins

  摘要：

  脂肪酶类似物环糊精（CD）可以在生理条件下选择性水解天然的溶血磷脂酰甘油（GPLs）。

  DOI：

  10.1039/d0sc05711h
• 作为产物：
  描述：

  油酸 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 水 、 氟化氢吡啶 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-油酰基-2-羟基-sn-甘油-3-磷酸乙醇胺
  参考文献：
  名称：

  Synthesis and evaluation of immunostimulant plasmalogen lysophosphatidylethanolamine and analogues for natural killer T cells

  摘要：

  Plasmalogen lysophosphatidylethanolamine (pLPE) had been identified as a self antigen for natural killer T cells (NKT cells). It is very important in the development, maturation and activation of NKT cells in thymus. Besides, pLPE is a novel type of antigen for NKT cells. To evaluate the structure-activity relationship (SAR) of this new antigen, pLPE and its analogues referred to different aliphatic chains and linkages at the sn-1 position of the glycerol backbone were synthesized, and the biological activities of these analogues was characterized. It is discovered that the linkages between phosphate and lipid moiety are not important for the antigens' activities. The pLPE analogues 1, 3, 4, 7 and 9, which have additional double bonds on lipid parts, were identified as new NKT agonists. Moreover, the analogues 4, 7 and 9 were discovered as potent Th2 activators for NKT cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.012

文献信息

• Polymerization of supramolecular assemblies: Comparison of lamellar and inverted hexagonal phases
  作者：Warunee Srisiri、Youn-Sik Lee、Thomas M. Sisson、Bruce Bondurant、David F. O'Brien

  DOI：10.1016/s0040-4020(97)00969-1

  日期：1997.11

  extended this strategy to successfully polymerize the inverted hexagonal (HII) phase. This report is the first comparison of radical chain polymerizations in lamellar and HII phases. The number average degree of polymerization of polymers obtained in both lamellar and HII phases depended strongly on the initiation chemistry, but were insensitive to the lipid phases. The immediate benefit of these studies

  自从1980年代初首次报道水合双层的聚合反应以来，已经成功地使用了多种可聚合基团和脂质。在探索用于层状相聚合的各种策略中，一种特别有用的方法依赖于合适的可聚合两亲物的设计，该两亲物在水合作用时可形成组装体，然后可在保留结构的情况下进行聚合。我们最近扩展了此策略，以成功地聚合倒六角形（H II）相。该报告是层状和H II相中自由基链聚合的首次比较。层状和H II中获得的聚合物的数均聚合度相对引发化学反应的依赖性很大，但对脂质相不敏感。这些研究的直接好处是，可以在两个阶段广泛改变聚合物的大小，以获得不同的材料性能。
• Discovery of a lysophospholipid acyltransferase family essential for membrane asymmetry and diversity
  作者：Daisuke Hishikawa、Hideo Shindou、Saori Kobayashi、Hiroki Nakanishi、Ryo Taguchi、Takao Shimizu

  DOI：10.1073/pnas.0712245105

  日期：2008.2.26

  All organisms consist of cells that are enclosed by a cell membrane containing bipolar lipids and proteins. Glycerophospholipids are important not only as structural and functional components of cellular membrane but also as precursors of various lipid mediators. Polyunsaturated fatty acids comprising arachidonic acid or eicosapentaenoic acid are located at sn -2 position, but not at sn -1 position of glycerophospholipids in an asymmetrical manner. In addition to the asymmetry, the membrane diversity is important for membrane fluidity and curvature. To explain the asymmetrical distribution of fatty acids, the rapid turnover of sn -2 position was proposed in 1958 by Lands [Lands WE (1958) Metabolism of glycerolipides: A comparison of lecithin and triglyceride synthesis. J Biol Chem 231:883–888]. However, the molecular mechanisms and biological significance of the asymmetry remained unknown. Here, we describe a putative enzyme superfamily consisting mainly of three gene families, which catalyzes the transfer of acyl-CoAs to lysophospholipids to produce different classes of phospholipids. Among them, we characterized three important enzymes with different substrate specificities and tissue distributions; one, termed lysophosphatidylcholine acyltransferase-3 (a mammalian homologue of Drosophila nessy critical for embryogenesis), prefers arachidonoyl-CoA, and the other two enzymes incorporate oleoyl-CoAs to lysophosphatidylethanolamine and lysophosphatidylserine. Thus, we propose that the membrane diversity is produced by the concerted and overlapped reactions with multiple enzymes that recognize both the polar head group of glycerophospholipids and various acyl-CoAs. Our findings constitute a critical milestone for our understanding about how membrane diversity and asymmetry are established and their biological significance.

  所有生物体都由细胞组成，这些细胞被包含双极脂质和蛋白质的细胞膜所包围。甘油磷脂不仅作为细胞膜的结构和功能组成部分，还是各种脂质介质的前体。由花生四烯酸或二十碳五烯酸组成的多不饱和脂肪酸位于甘油磷脂的不对称的sn-2位置，而不是sn-1位置。除了不对称性外，膜的多样性对于膜的流动性和曲率也很重要。为了解释脂肪酸的不对称分布，1958年Lands提出了sn-2位置的快速周转。然而，不对称性的分子机制和生物学意义仍然未知。在这里，我们描述了一个潜在的酶超家族，主要由三个基因家族组成，它们催化酰基辅酶A转移至溶血磷脂，以产生不同类别的磷脂。其中，我们表征了三种具有不同底物特异性和组织分布的重要酶；一种被称为溶血磷脂酰转移酶-3（果蝇nessy的哺乳动物同源物，对胚胎发育至关重要），更喜欢花生四烯酰辅酶A，而另外两种酶则将油酰辅酶A并入到溶血磷脂酰乙醇胺和溶血磷脂酰丝氨酸中。因此，我们提出，膜的多样性是由多个酶的协同和重叠反应产生的，这些酶识别甘油磷脂的极性头基和各种酰基辅酶A。我们的发现对于我们理解膜的多样性和不对称性的建立及其生物学意义构成了一个关键的里程碑。
• ABHD12 controls brain lysophosphatidylserine pathways that are deregulated in a murine model of the neurodegenerative disease PHARC
  作者：Jacqueline L. Blankman、Jonathan Z. Long、Sunia A. Trauger、Gary Siuzdak、Benjamin F. Cravatt

  DOI：10.1073/pnas.1217121110

  日期：2013.1.22

  Advances in human genetics are leading to the discovery of new disease-causing mutations at a remarkable rate. Many such mutations, however, occur in genes that encode for proteins of unknown function, which limits our molecular understanding of, and ability to devise treatments for, human disease. Here, we use untargeted metabolomics combined with a genetic mouse model to determine that the poorly characterized serine hydrolase α/β-hydrolase domain-containing (ABHD)12, mutations in which cause the human neurodegenerative disorder PHARC (polyneuropathy, hearing loss, ataxia, retinosis pigmentosa, and cataract), is a principal lysophosphatidylserine (LPS) lipase in the mammalian brain. ABHD12 ^−/− mice display massive increases in a rare set of very long chain LPS lipids that have been previously reported as Toll-like receptor 2 activators. We confirm that recombinant ABHD12 protein exhibits robust LPS lipase activity, which is also substantially reduced in ABHD12 ^−/− brain tissue. Notably, elevations in brain LPS lipids in ABHD12 ^−/− mice occur early in life (2–6 mo) and are followed by age-dependent increases in microglial activation and auditory and motor defects that resemble the behavioral phenotypes of human PHARC patients. Taken together, our data provide a molecular model for PHARC, where disruption of ABHD12 causes deregulated LPS metabolism and the accumulation of proinflammatory lipids that promote microglial and neurobehavioral abnormalities.

  人类遗传学的进步正在以惊人的速度导致新的疾病致病突变的发现。然而，许多这样的突变发生在编码未知功能蛋白质的基因中，这限制了我们对人类疾病的分子理解和制定治疗方案的能力。在这里，我们使用非定向代谢组学结合遗传小鼠模型，确定了一种鲜为人知的丝氨酸水解酶α/β-水解酶结构域含有（ABHD）12，其突变导致人类神经退行性疾病PHARC（多发性神经病、听力损失、共济失调、视网膜色素变性和白内障），是哺乳动物大脑中主要的溶血磷脂酰丝氨酸（LPS）脂肪酶。ABHD12 ^-/- 小鼠显示出一组罕见的非常长链LPS脂质的大量增加，这些脂质以前已被报道为Toll样受体2激活剂。我们确认重组ABHD12蛋白表现出强大的LPS脂肪酶活性，这在ABHD12 ^-/- 脑组织中也显著降低。值得注意的是，ABHD12 ^-/- 小鼠脑中的LPS脂质升高发生在早期（2-6个月），随后是年龄相关的小胶质细胞激活和听觉和运动缺陷的增加，这类似于人类PHARC患者的行为表型。综上所述，我们的数据为PHARC提供了一个分子模型，其中ABHD12的破坏导致LPS代谢的失调和促进小胶质细胞和神经行为异常的炎症脂质的积累。
• Cloning of Glycerophosphocholine Acyltransferase (GPCAT) from Fungi and Plants
  作者：Bartosz Głąb、Mirela Beganovic、Sanket Anaokar、Meng-Shu Hao、Allan G. Rasmusson、Jana Patton-Vogt、Antoni Banaś、Sten Stymne、Ida Lager

  DOI：10.1074/jbc.m116.743062

  日期：2016.11

  extracts from yeast and plants could acylate GPC with acyl groups from acyl-CoA. By screening enzyme activities of extracts derived from a yeast knock-out collection, we were able to identify and clone the yeast gene (GPC1) encoding the enzyme, named glycerophosphocholine acyltransferase (GPCAT). By homology search, we also identified and cloned GPCAT genes from three plant species. All enzymes utilize

  长期以来一直认为磷脂酰胆碱（PC）完全脱酰的产物甘油3-磷酸胆碱（GPC）并不是再酰化的底物。然而，最近显示，来自酵母和植物的无细胞提取物可将GPC与来自酰基辅酶A的酰基酰化。通过筛选来自酵母敲除集合的提取物的酶活性，我们能够鉴定和克隆编码该酶的酵母基因（GPC1），称为甘油磷酸胆碱酰基转移酶（GPCAT）。通过同源搜索，我们还从三种植物中鉴定并克隆了GPCAT基因。所有酶都利用酰基辅酶A酰化GPC，形成溶血PC，并且它们在酵母和植物中均显示出广泛的酰基特异性。除酰基辅酶A外，GPCAT还有效地利用LPC和溶血磷脂酰乙醇胺作为酰基化GPC的酰基供体。在主要的真核生物组中发现了GPCAT同源物，但在原核生物或脊索动物中未发现GPCAT同源物。该酶形成自己的蛋白质家族，不包含其他研究过的酰基转移酶和转酰酶中存在的任何酰基结合或脂肪酶基序。体内标记研究证实了Gpc1p在酵母PC生物合成中的作用。
• Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids
  作者：Qiongqiong Wan、Yanan Xiao、Guifang Feng、Xin Dong、Wenjing Nie、Ming Gao、Qingtao Meng、Suming Chen

  DOI：10.1016/j.cclet.2023.108775

  日期：2024.4

  increases the complexity of lipid structures. The C=C bond location and -position are two of the essential attributes that determine the structures of unsaturated lipids. However, simultaneous identification of both attributes remains challenging. Here, we develop a visible-light-activated aziridination reaction system, which enables the dual-resolving of the C=C bond location and -position isomerism of in

  脂质的生物学功能与其结构有着密切的关系，各种异构体大大增加了脂质结构的复杂性。 C=C键位置和-位置是决定不饱和脂质结构的两个基本属性。然而，同时识别这两种属性仍然具有挑战性。在这里，我们开发了一种可见光激活的氮丙啶化反应系统，与液相色谱-质谱（LC-MS）相结合，能够双重解析脂质中的C=C键位置和位置异构现象。基于 C=C 键与 PhI=NT 的衍生化，它们在脂质中的位置可以通过串联 MS 轻松识别。特别是，不饱和磷脂酰胆碱(PC)的β位异构体可以在衍生化后通过LC-MS进行分离和定量。通过使用所提出的方法，揭示了PC的β位异构体比例在小鼠脑缺血中的显着变化。这项研究为深层脂质结构生物学提供了强大的工具。