L-(+)-2-Linoleoyl-3-oleoyl-glycerin-1-phosphorsaeure-(2-amino-aethylester) | 1188-56-3

• 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: L-(+)-2-Linoleoyl-3-oleoyl-glycerin-1-phosphorsaeure-(2-amino-aethylester)
• 英文别名: 1-Oleoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine；2-azaniumylethyl (2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphate；2-azaniumylethyl [(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropyl] phosphate
• CAS: 1188-56-3
• 化学式: C₄₁H₇₆NO₈P
• 分子量: 742.03
• InChiKey: GKAFCSRKMWFPSJ-RJXNKANHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  51
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2-二油酰基-sn-甘油 、 L-(+)-2-Linoleoyl-3-oleoyl-glycerin-1-phosphorsaeure-(2-amino-aethylester) 生成 1,2-Dioleoyl-3-linoleoyl-sn-glycerol 、 1-油酰基-2-羟基-sn-甘油-3-磷酸乙醇胺
  参考文献：
  名称：

  Saccharomyces cerevisiae phospholipid:diacylglycerol acyl transferase (PDAT) devoid of its membrane anchor region is a soluble and active enzyme retaining its substrate specificities

  摘要：

  A N-terminal deleted version of the Saccharomyces cerevisiae phospholipid:diacylglycerol acyltransferase (ScPDAT), lacking the predicted membrane-spanning region, was fused in frame with alpha-factor secretion signal and expressed in Pichia pastoris under the control of the methanol inducible alcohol oxidase promoter. This resulted in a truncated, soluble and highly active PDAT protein secreted into the culture medium of the recombinant cells. The soluble as well as native membrane bound enzymes was shown to be glycosylated and extensive deglycosylation severely lowered the activity. The production of a soluble and extracellular PDAT allowed us to investigate substrate preferences of the enzyme without interference of endogenous lipids and enzymes. Similar to the membrane bound counterpart, the highest activity was achieved with acyl groups at sn-2 position of phosphatidylethanolamine as acyl donor and 1,2-diacylglycerols as acyl acceptor. The soluble enzyme was also able to catalyze, at a low rate, a number of transacylation reactions between various neutral lipids and between polar lipids and neutral lipids others than diacylglycerols, including acylation of long chain alcohols. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbalip.2007.10.007
• 作为产物：
  描述：

  L-2-Linoleoyl-3-oleoyl-glycerin-1-phosphorsaeure-(2-phthalimido-ethylester) 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 L-(+)-2-Linoleoyl-3-oleoyl-glycerin-1-phosphorsaeure-(2-amino-aethylester)
  参考文献：
  名称：

  Investigations in the field of complex lipids

  摘要：

  DOI：

  10.1007/bf00567534

文献信息

• 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。
• Derivate des Glycerophosphocholins und Glycerophosphoethanolamins, ihre Herstellung und Verwendung
  申请人：CHEMIE LINZ AKTIENGESELLSCHAFT

  公开号：EP0161519B1

  公开（公告）日：1988-06-29
• US4622180A
  申请人：——

  公开号：US4622180A

  公开（公告）日：1986-11-11
• US4717512A
  申请人：——

  公开号：US4717512A

  公开（公告）日：1988-01-05
• Volkova,L.V. et al., Journal of General Chemistry of the USSR, <hi>1965</hi>, vol. 35, p. 82 - 83
  作者：Volkova,L.V. et al.

  DOI：——

  日期：——