1-棕榈-sn-甘油-3-磷酸乙醇胺 | 53862-35-4

• 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-棕榈-sn-甘油-3-磷酸乙醇胺
• 英文名称: 1-O-hexadecanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
• 英文别名: 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphatidylethanolamine；1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine；1-hexadecanoyl-sn-glycero-3-phosphoethanolamine；1-palmitoyl-sn-glycero-3-phosphoethanolamine；LysoPE(16:0/0:0)；palmitoyl-LPE；2-azaniumylethyl [(2R)-3-hexadecanoyloxy-2-hydroxypropyl] phosphate
• CAS: 53862-35-4
• 化学式: C₂₁H₄₄NO₇P
• 分子量: 453.557
• InChiKey: YVYMBNSKXOXSKW-HXUWFJFHSA-N

物化性质

• 溶解度：
  氯仿：微溶； DMF：微溶； DMSO：微溶
• 物理描述：
  Solid
• 碰撞截面：
  206.89 Ų [M-H]- [CCS Type: TW, Method: calibrated with phosphatidylcholines (ESI+) and phosphatidylethanolamines (ESI-) doubly charged cardiolipins calibrated with poly-DL-alanine]
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  8

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1-棕榈-sn-甘油-3-磷酸乙醇胺 在 4-二甲氨基吡啶 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 120.0h， 生成 1-palmitoyl-2-(5-hexenoyl)-sn-glycero-3-phosphatidyl-(2-trimethylsilanylethoxycarbonylamino)ethanol
  参考文献：
  名称：

  Total Syntheses of Bioactive Oxidized Ethanolamine Phospholipids

  摘要：

  GraphicsTruncated ethanolamine phospholipids containing aldehyde functionality, e.g. OVPE, and the corresponding acids, are generated by oxidative cleavage of polyunsaturated phospholipids. To confirm their identities and facilitate studies of the chemistry and biological actions of these analogues of biologically active phosphatidylcholines, e.g. OVPC, total syntheses were developed. An efficient general strategy was used that features selective N-protection of 2-lysophosphatidylethanolamine, and generation of the target compounds by mild deprotection of stable precursors.

  DOI：

  10.1021/ol034729z
• 作为产物：
  描述：

  (S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-hexadecanoate 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 、 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-棕榈-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

• Synthesis of a Polymerizable Metal-Ion-Chelating Lipid for Fluid Bilayers
  作者：Sang Won Jeong、David F. O'Brien

  DOI：10.1021/jo0100796

  日期：2001.7.1

  Hydrated lipid structures, such as liposomes, that display tethered metal-ion-chelating groups have proven useful in peptide and protein binding, as well as 2D protein crystallization through molecular recognition of accessible histidine sites in proteins and peptides. Polymerizable metal-ion-chelating lipids bearing a reactive diacetylene group have been described. These interesting compounds can

  表现出束缚的金属离子螯合基团的水合脂质结构（例如脂质体）已证明可用于肽和蛋白质结合，以及通过分子识别蛋白质和肽中可接近的组氨酸位点来进行2D蛋白质结晶。已经描述了带有反应性二乙炔基的可聚合的金属离子螯合脂质。这些有趣的化合物可以在固相中聚合。在此，我们描述了可用于脂质双层的流体（即类似液体）相的第一种可聚合金属离子螯合脂质的设计。1-棕榈酰基-2- [8-[（E，E）-2'，4'-己二酰氧基]辛酰基] -sn-甘油-3-N- [11- [N'，N'-bis [描述了羧甲基]亚氨基] -3,6,9-三氧杂十二烷酰基]磷脂酰乙醇胺（1）。螯合剂亚氨基二乙酸酯（IDA）通过基于低聚（乙二醇）的间隔基连接到具有末端2，4-己二酰基（山梨酰基）的可聚合磷脂酰乙醇胺（PE）。设计脂质1-Cu复合物，使其与相应的可聚合基质脂质（bis-SorbPC）结合，形成可以通过各种聚合方法稳定的功能化脂质体。
• Myeloperoxidase-derived 2-chlorohexadecanal forms Schiff bases with primary amines of ethanolamine glycerophospholipids and lysine
  作者：Kristin R. Wildsmith、Carolyn J. Albert、Fong-Fu Hsu、Jeff L.-F. Kao、David A. Ford

  DOI：10.1016/j.chemphyslip.2005.12.003

  日期：2006.2

  adducts with ethanolamine glycerophospholipids and Fmoc-lysine. Utilizing electrospray ionization mass spectrometry, chlorinated adducts were observed that are apparent Schiff base adducts. Reduction of these Schiff base adducts with sodium cyanoborohydride resulted in a novel, stable adduct produced by the elimination of HCl. NMR further confirmed this structure. 2-ClHDA adducts with ethanolamine glycerophospholipids

  大量研究表明，髓过氧化物酶，炎症和动脉粥样硬化之间存在相关性。MPO衍生的反应性氯化物（RCS）攻击膜缩醛磷脂，释放出包括2-氯十六醛（2-ClHDA）的α-氯脂肪醛（alpha-Cl-FALD）。α-Cl-FALD的分子靶标是未知的。目前的研究表明2-ClHDA与乙醇胺甘油磷脂和Fmoc-赖氨酸的加合物。利用电喷雾电离质谱法，观察到氯化加合物是明显的席夫碱加合物。用氰基硼氢化钠还原这些席夫碱加合物会产生一种新的稳定的加合物，该加合物通过消除HCl生成。NMR进一步证实了该结构。乙醇胺甘油磷脂的2-ClHDA加合物也是磷脂酶D（PLD）的底物。将水解产物衍生为五氟苯甲酸酯，并通过GC-MS进一步结构确认。在用2-ClHDA处理的内皮细胞中观察到2-ClHDA-N-修饰的乙醇胺甘油磷脂的多种分子种类。这些结果显示了α-Cl-FALD与伯胺的新型席夫碱加合物，这可能代表了α-Cl-FALD的重要命运。
• 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。
• Mycobacterium tuberculosis Rv3802c Encodes a Phospholipase/Thioesterase and Is Inhibited by the Antimycobacterial Agent Tetrahydrolipstatin
  作者：Sarah K. Parker、Robert M. Barkley、John G. Rino、Michael L. Vasil

  DOI：10.1371/journal.pone.0004281

  日期：——

  location in a mycolic acid synthesis gene cluster, its putative essentiality, its ubiquitous presence in actinomycetes, and its conservation in the minimal genome of Mycobacterium leprae. We expressed Rv3802 in Escherichia coli and purified the enzymatically active form. We probed its activities and inhibitors characterizing those relevant to its possible role in mycolic acid biosynthesis. In addition

  结核分枝杆菌的细胞壁是其成功成为病原体的关键。霉菌酸是这种细胞壁的关键成分。参与连接 alpha 和 mero 分枝杆菌的基因位于一个簇中，从 Rv3799c 开始并至少延伸到 Rv3804c。除了 Rv3802c 之外，由这五个基因编码的每种酶的作用都相当清楚。Rv3802 是由结核分枝杆菌基因组编码的七种推定角质酶之一。在植物病原体中，角质酶水解植物的蜡质层，角质。在严格的哺乳动物病原体中，例如结核分枝杆菌，这些蛋白质很可能执行不同的功能。在这七种中，我们选择关注 Rv3802c，因为它位于分枝杆菌酸合成基因簇中，它被认为是必不可少的，它在放线菌中无处不在，及其在麻风分枝杆菌最小基因组中的保守性。我们在大肠杆菌中表达了 Rv3802 并纯化了具有酶活性的形式。我们探讨了它的活性和抑制剂，表征了与其在分枝杆菌酸生物合成中的可能作用相关的那些。除了其报道的磷脂酶 A 活性外，Rv3802 还具有显着的硫酯酶活性，并被四氢脂抑素
• <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。