1-棕榈酰基-2-亚油酰基PE | 26662-95-3

• 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-棕榈酰基-2-亚油酰基PE
• 英文名称: 2-O-linoleoyl-1-O-palmitoyl-sn-glycero-3-phosphoethanolamine
• 英文别名: 1-palmitoyl-2-linoleoylphosphatidylethanolamine；(2-aminoethoxy)[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid；1-palmitoyl-2-linoleoyl pe；PE-C16:0/C18:2；γ-Palmitoyl-β-linoleoyl-L-α-phosphatidyl-aethanolamin；PE(16:0/18:2)；PLPE；1-16:0-2-18:2-Phosphatidylethanolamine；2-azaniumylethyl [(2R)-3-hexadecanoyloxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] phosphate
• CAS: 26662-95-3；97281-51-1
• 化学式: C₃₉H₇₄NO₈P
• 分子量: 715.992
• InChiKey: HBZNVZIRJWODIB-NHCUFCNUSA-N

物化性质

• 溶解度：
  氯仿：50mg/mL；乙醇：1mg/mL；甲醇：5mg/mL
• 物理描述：
  Solid
• 碰撞截面：
  283.8 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  49
• 可旋转键数：
  39
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  9

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1-棕榈酰基-2-亚油酰基PE 在 phospholipase A2 作用下， 生成 1-棕榈-sn-甘油-3-磷酸乙醇胺
  参考文献：
  名称：

  Lysophosphatidylethanolamine is – in contrast to – choline – generated under in vivo conditions exclusively by phospholipase A2 but not by hypochlorous acid

  摘要：

  Inflammatory liver diseases are associated with oxidative stress mediated particularly by neutrophilic granulocytes. At inflammatory loci, hypochlorous acid (HOCl) is generated by myeloperoxidase. HOCl reacts with a large variety of molecules and induces (among other reactions) the formation of lysophosphatidylcholine (LPC) from polyunsaturated phosphatidylcholines (PC).As liver tissue contains huge amounts of polyunsaturated PC species enhanced LPC concentrations are detectable under these conditions. However, human liver contains also major amounts of polyunsaturated phosphatidylethanolamine (PE). It is so far widely unknown, if PE oxidation by HOCl leads to the generation of LPE in a similar way as observed in the case of PC. Using MALDI-TOF mass spectrometry (MS) and P-31 NMR spectroscopy, LPC generation from unsaturated PC could be verified in the presence of HOCl. In contrast, unsaturated PE led exclusively to chlorohydrins and other oxidation products but not to LPE.Although these data were obtained with a quite simple model system, it is obvious that LPC is a much more suitable biomarker of oxidative stress than LPE: LPC is more readily generated and also more sensitively detectable by means of mass spectrometry and other spectroscopic methods. Nevertheless, it will also be shown that the nitrile of LPE is also generated. However, this compound is exclusively detectable as negative ion. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2009.09.002
• 作为产物：
  描述：

  O-<2-(N-(tert-butyloxycarbonyl)amino)ethyl> O-methyl O-(1'-O-palmitoyl-sn-3'-glyceryl) phosphate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 6.0h， 生成 1-棕榈酰基-2-亚油酰基PE
  参考文献：
  名称：

  General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols

  摘要：

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.

  DOI：

  10.1021/jo00096a023

文献信息

• Functional associative coatings for nanoparticles
  申请人：Hainfeld James F.

  公开号：US20080089836A1

  公开（公告）日：2008-04-17

  Described herein are nanoparticles that are coated with a bilayer of molecules formed from surface binding molecules and amphiphatic molecules. The bilayer coating self assembles on the nanoparticles from readily available materials/molecules. The modular design of the bilayer coated nanoparticles provides a means for readily and efficiently optimizing the properties of the bilayer coated nanoparticle compositions. Also described herein are uses of such nanoparticles in medicine, laboratory techniques, industrial and commerical applications.

  本文描述了一种纳米颗粒，其表面涂覆有由表面结合分子和两亲分子形成的双层分子层。该双层涂层可以自组装在纳米颗粒上，使用易得的材料/分子。双层涂层纳米颗粒的模块化设计提供了一种方便和高效地优化其性质的方法。此外，本文还描述了这种纳米颗粒在医学、实验室技术、工业和商业应用中的用途。
• 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。
• <i>Drosophila</i>Lysophospholipid Acyltransferases Are Specifically Required for Germ Cell Development
  作者：Josefa Steinhauer、Miguel A. Gijón、Wayne R. Riekhof、Dennis R. Voelker、Robert C. Murphy、Jessica E. Treisman

  DOI：10.1091/mbc.e09-05-0382

  日期：2009.12.15

  Enzymes of the membrane-bound O-acyltransferase (MBOAT) family add fatty acyl chains to a diverse range of protein and lipid substrates. A chromosomal translocation disrupting human MBOAT1 results in a novel syndrome characterized by male sterility and brachydactyly. We have found that the Drosophila homologues of MBOAT1, Oysgedart (Oys), Nessy (Nes), and Farjavit (Frj), are lysophospholipid acyltransferases. When expressed in yeast, these MBOATs esterify specific lysophospholipids preferentially with unsaturated fatty acids. Generating null mutations for each gene allowed us to identify redundant functions for Oys and Nes in two distinct aspects of Drosophila germ cell development. Embryos lacking both oys and nes show defects in the ability of germ cells to migrate into the mesoderm, a process guided by lipid signals. In addition, oys nes double mutant adult males are sterile due to specific defects in spermatid individualization. oys nes mutant testes, as well as single, double, and triple mutant whole adult animals, show an increase in the saturated fatty acid content of several phospholipid species. Our findings suggest that lysophospholipid acyltransferase activity is essential for germline development and could provide a mechanistic explanation for the etiology of the human MBOAT1 mutation.

  膜结合O-酰转移酶（MBOAT）家族的酶可以向多种蛋白质和脂质底物中加入脂肪酰基。破坏人类MBOAT1的染色体易位导致一种新的综合症，其特征为男性不育和短指。我们发现果蝇MBOAT1的同源物Oysgedart（Oys）、Nessy（Nes）和Farjavit（Frj）是溶解磷脂酰基转移酶。当在酵母中表达这些MBOAT时，它们会选择性地酯化特定的溶解磷脂酰基，特别是不饱和脂肪酸。通过产生每个基因的空突变，我们确定了Oys和Nes在果蝇生殖细胞发育的两个不同方面中具有冗余功能。缺乏oys和nes的胚胎显示出生殖细胞进入中胚层的能力受到缺陷，这是由脂质信号引导的过程。此外，oys nes双突变体成年雄性不育，由于精子个体化的特定缺陷。oys nes突变体睾丸以及单个、双重和三重突变体的整个成年动物显示出多种磷脂酰基中饱和脂肪酸含量的增加。我们的发现表明，溶解磷脂酰基转移酶活性对生殖细胞发育至关重要，并可以为人类MBOAT1突变的病因提供机制解释。
• Positional specificity of lysosomal phospholipase A2
  作者：Akira Abe、Miki Hiraoka、James A. Shayman

  DOI：10.1194/jlr.m600183-jlr200

  日期：2006.10

  5-fold higher than that of 1-O-palmitoyl-NAS. Thus, Lpla2 can act on acyl groups at both sn-1 and sn-2 positions of POPC and OPPC. When 1-palmitoyl-2-unsaturated acyl-sn-glycero-3-phosphocholines were used as acyl donors, the transacylation of the acyl group from the sn-2 position to NAS was preferred to that of the palmitoyl group from the sn-1 position. An exception was observed for 1-palmitoyl-2-ar

  溶酶体磷脂酶A（2）（Lpla2）在肺泡巨噬细胞中高度表达，并可能介导表面活性剂的磷脂代谢。对这种磷脂酶特性的研究与磷脂酶A（1）和磷脂酶A（2）活性的存在是一致的。通过生产由Lpla2的转酰酶活性产生的O-酰基化合物来研究这些活性。将含有POPC和N-乙酰基鞘氨醇（NAS）的脂质体与从稳定转染了小鼠Lpla2基因的MDCK细胞获得的可溶性级分一起孵育。Lpla2生产了两个1-O-酰基-NAS，1-O-棕榈酰基-NAS和1-O-油酰基-NAS。1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的2.5倍。当使用1-油酰基-2-棕榈酰基-sn-甘油-3-磷酸胆碱（OPPC）时，1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的5倍。因此，Lpla2可以在POPC和OPPC的sn-1和sn-2位置同时作用于酰基。当使用1-棕榈酰基-2-不饱和酰基-sn-甘油-3-磷酸胆碱作为
• Formation of molecular species of mitochondrial cardiolipin. 1. A novel transacylation mechanism to shuttle fatty acids between sn-1 and sn-2 positions of multiple phospholipid species
  作者：Ashim Malhotra、Yang Xu、Mindong Ren、Michael Schlame

  DOI：10.1016/j.bbalip.2009.01.004

  日期：2009.4

  of phospholipase A(2) because it requires only trace amounts of lysophospholipids. We show that purified tafazzin reacts with various phospholipid classes and with various acyl groups both in sn-1 and sn-2 position. Expression studies in Sf9 insect cells suggest that the effect of tafazzin on cardiolipin species is dependent on the cellular environment and not on enzymatic substrate specificity. Our

  线粒体心磷脂对其酰基进行了广泛的重塑，以产生均匀取代的物种，例如四亚油酰心磷脂，但这种重塑的机制尚未阐明，除了它需要 tafazzin 之外。在这里，我们显示纯化的重组果蝇 tafazzin 通过正向和反向转移的组合在心磷脂和磷脂酰胆碱之间交换酰基。在没有磷脂酶 A(2) 的情况下，酰基交换是可能的，因为它只需要微量的溶血磷脂。我们表明纯化的 tafazzin 与各种磷脂类以及 sn-1 和 sn-2 位置的各种酰基反应。Sf9 昆虫细胞中的表达研究表明，tafazzin 对心磷脂种类的影响取决于细胞环境，而不是酶底物特异性。我们的数据表明，tafazzin 催化磷脂之间的一般酰基交换，这提出了一个问题，即心磷脂中的模式形成是否是多种磷脂物种之间酰基平衡分布的结果。