1-O-palmitoyl-2-arachidonoyl-glycerol | 65886-78-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-O-palmitoyl-2-arachidonoyl-glycerol
• 英文别名: 1-Palmitoyl-2-arachidonoyl-sn-glycerol；[(2S)-1-hexadecanoyloxy-3-hydroxypropan-2-yl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 65886-78-4
• 化学式: C₃₉H₆₈O₅
• 分子量: 616.966
• InChiKey: YJEMDFYSDGNQNM-NDUZERMISA-N

物化性质

• 沸点：
  669.4±55.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  44
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氯乙基二氯磷酸 、 1-O-palmitoyl-2-arachidonoyl-glycerol 、 三甲胺 在 三乙胺 、 水 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 72.0h， 以63.5%的产率得到2-花生四烯酰-1-棕榈酰-sn-甘油-3-磷酸胆碱
  参考文献：
  名称：

  Synthesis of a Small Library of Mixed-Acid Phospholipids from D-Mannitol as a Homochiral Starting Material.

  摘要：

  描述了一种使用新保护策略合成一系列含有多不饱和脂肪酸的混酸磷脂。具体而言，分别用BCl3和354 nm的光去除的保护基团是苄基和甲基α-(2, 4-二硝基苯基)乙酸。

  DOI：

  10.1248/cpb.47.1659
• 作为产物：
  描述：

  花生四烯酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 1-O-palmitoyl-2-arachidonoyl-glycerol
  参考文献：
  名称：

  Synthesis of a Small Library of Mixed-Acid Phospholipids from D-Mannitol as a Homochiral Starting Material.

  摘要：

  描述了一种使用新保护策略合成一系列含有多不饱和脂肪酸的混酸磷脂。具体而言，分别用BCl3和354 nm的光去除的保护基团是苄基和甲基α-(2, 4-二硝基苯基)乙酸。

  DOI：

  10.1248/cpb.47.1659

文献信息

• RAMESHA, CHAKKODABYLU S.;PICKETT, WALTER C.;KRISHNA, MURTHY D. V., J. CHROMATOGR. BIOMED. APPL., 491,(1989) N, C. 37-48
  作者：RAMESHA, CHAKKODABYLU S.、PICKETT, WALTER C.、KRISHNA, MURTHY D. V.

  DOI：——

  日期：——
• Characterization of the Human LPIN1-encoded Phosphatidate Phosphatase Isoforms
  作者：Gil-Soo Han、George M. Carman

  DOI：10.1074/jbc.m110.117747

  日期：2010.5

  The human LPIN1 gene encodes the protein lipin 1, which possesses phosphatidate (PA) phosphatase (3-sn-phosphatidate phosphohydrolase; EC 3.1.3.4) activity (Han, G.-S., Wu, W.-I., and Carman, G. M. (2006) J. Biol. Chem. 281, 9210-9218). In this work, we characterized human lipin 1 alpha, beta, and gamma isoforms that were expressed in Escherichia coli and purified to near homogeneity. PA phosphatase activities of the alpha, beta, and gamma isoforms were dependent on Mg2+ or Mn2+ ions at pH 7.5 at 37 degrees C. The activities were inhibited by concentrations of Mg2+ and Mn2+ above their optimums and by Ca2+, Zn2+, N-ethylmaleimide, propranolol, and the sphingoid bases sphingosine and sphinganine. The activities were thermally labile at temperatures above 40 degrees C. The alpha, beta, and gamma activities followed saturation kinetics with respect to the molar concentration of PA (K-m values of 0.35, 0.24, and 0.11 mM, respectively) but followed positive cooperative (Hill number similar to 2) kinetics with respect to the surface concentration of PA (K-m values of 4.2, 4.5, and 4.3 mol %, respectively) in Triton X-100/PA-mixed micelles. The turnover numbers (k(cat)) for the alpha, beta, and gamma isoforms were 68.8 +/- 3.5, 42.8 +/- 2.5, and 5.7 +/- 0.2 s(-1), respectively, whereas their energy of activation values were 14.2, 15.5, and 18.5 kcal/mol, respectively. The isoform activities were dependent on PA as a substrate and required at least one unsaturated fatty acyl moiety for maximum activity.
• Diacylglycerol Kinase ϵ Is Selective for Both Acyl Chains of Phosphatidic Acid or Diacylglycerol
  作者：Michael Lung、Yulia V. Shulga、Pavlina T. Ivanova、David S. Myers、Stephen B. Milne、H.Alex Brown、Matthew K. Topham、Richard M. Epand

  DOI：10.1074/jbc.m109.050617

  日期：2009.11

  The phosphatidylinositol ( PI) cycle mediates many cellular events by controlling the metabolism of many lipid second messengers. Diacylglycerol kinase epsilon (DGK epsilon) has an important role in this cycle. DGK epsilon is the only DGK isoform to show inhibition by its product phosphatidic acid (PA) as well as substrate specificity for sn-2 arachidonoyl-diacylglycerol (DAG). Here, we show that this inhibition and substrate specificity are both determined by selectivity for a combination of the sn-1 and sn-2 acyl chains of PA or DAG, respectively, preferring the most prevalent acyl chain composition of lipids involved specifically in the PI cycle, 1-stearoyl-2-arachidonoyl. Although the difference in rate for closely related lipid species is small, there is a significant enrichment of 1-stearoyl-2-arachidonoyl PI because of the cyclical nature of PI turnover. Wealso show that the inhibition of DGK epsilon by PA is competitive and that the deletion of the hydrophobic segment and cationic cluster of DGK epsilon does not affect its selectivity for the acyl chains of PA or DAG. Thus, this active site not only recognizes the lipid headgroup but also a combination of the two acyl chains in PA or DAG. We propose a mechanism of DGK epsilon regulation where its dual acyl chain selectivity is used to negatively regulate its enzymatic activity in a manner that ensures DGK epsilon remains committed to the PI turnover cycle. This novel mechanism of enzyme regulation within a signaling pathway could serve as a template for the regulation of enzymes in other pathways in the cell.
• METHODS OF TREATING RENAL DISEASE
  申请人：The Regents of the University of California

  公开号：EP3823610A1

  公开（公告）日：2021-05-26
• [EN] METHODS OF TREATING RENAL DISEASE<br/>[FR] MÉTHODES DE TRAITEMENT D'UNE MALADIE RÉNALE
  申请人：UNIV CALIFORNIA

  公开号：WO2020018554A1

  公开（公告）日：2020-01-23

  Disclosed herein, inter alia, are methods of treating renal disease (e.g., chronic kidney disease or end stage renal disease).