1,2-二油酰基-sn-甘油-3-磷酸乙醇胺-N,N-二甲基 | 96687-22-8

• 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: 1,2-二油酰基-sn-甘油-3-磷酸乙醇胺-N,N-二甲基
• 英文名称: (2R)-3-(((2-(dimethylamino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl dioleate
• 英文别名: 1,2-dioleoyl-sn-glycero-3-phosphocholine；DOPC；(2R)-2,3-bis{[(9Z)-octadec-9-enoyl]oxy}propyl 2-(dimethylazaniumyl)ethyl phosphate；[(2R)-2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl] 2-(dimethylazaniumyl)ethyl phosphate
• CAS: 96687-22-8
• 化学式: C₄₃H₈₂NO₈P
• 分子量: 772.1
• InChiKey: XHPZRQBHFOVLEJ-UNUIOPIBSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  53
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-甲氧基乙氧基甲基氯 、 1,2-二油酰基-sn-甘油-3-磷酸乙醇胺-N,N-二甲基 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以30%的产率得到[(2R)-3-[2-(dimethylamino)ethoxy-(2-methoxyethoxymethoxy)phosphoryl]oxy-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
  参考文献：
  名称：

  IONIZABLE COMPOUNDS AND COMPOSITIONS AND USES THEREOF

  摘要：

  这项发明涉及可离子化的化合物，以及其组合物和使用方法。这些可离子化的化合物可用于制备纳米粒子组合物，用于生物制药和治疗。更具体地说，这项发明涉及提供纳米粒子以包裹活性剂，如核酸剂，并将活性剂传递和分发到细胞、组织、器官和受试者的化合物、组合物和方法。

  公开号：

  US20160376229A1
• 作为产物：
  描述：

  N-甲基-1,2-二油酰基磷脂酰乙醇胺 、 S-腺苷蛋氨酸 生成 1,2-二油酰基-sn-甘油-3-磷酸乙醇胺-N,N-二甲基 、 氢(+1)阳离子 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  Membrane Topography of Human Phosphatidylethanolamine N-Methyltransferase

  摘要：

  In liver, phosphatidylethanolamine is converted to phosphatidylcholine through a series of three sequential methylation reactions. Phosphatidylethanolamine N-methyltransferase (PEMT) catalyzes each transmethylation reaction, and S-adenosylmethionine is the methyl group donor. Biochemical analysis of human liver revealed that the methyltransferase activity is primarily localized to the endoplasmic reticulum and mitochondria-associated membranes. Bioinformatic analysis of the predicted amino acid sequence suggested that the enzyme adopts a polytopic conformation in those membranes. To elucidate the precise membrane topography of PEMT and thereby provide the basis for in-depth functional characterization of the enzyme, we performed endoproteinase-protection analysis of epitope-tagged, recombinant protein. Our data suggest a topographical model of PEMT in which four transmembrane regions span the membrane such that both the N and C termini of the enzyme are localized external to the ER. Two hydrophilic connecting loops protrude into the luminal space of the microsomes whereas a corresponding loop on the cytosolic side remains proximate to the membrane. Further support for this model was obtained following endoproteinase-protection analysis of mutant recombinant PEMT derivatives in which specific protease cleavage sites had been genetically engineered or ablated.

  DOI：

  10.1074/jbc.m210904200

文献信息

• Localization-independent Regulation of Homocysteine Secretion by Phosphatidylethanolamine N-Methyltransferase
  作者：David J. Shields、Susanne Lingrell、Luis B. Agellon、John T. Brosnan、Dennis E. Vance

  DOI：10.1074/jbc.m504658200

  日期：2005.7

  Genetic ablation of phosphatidylethanolamine N-methyltransferase (PEMT) in mice causes a 50% reduction in plasma homocysteine (Hcy) levels. Because hyperhomocysteinemia is an independent risk factor for cardiovascular disease, resolution of the molecular basis for this reduction is of significant clinical interest. The PEMT pathway is a metabolically channeled process localized to the endoplasmic reticulum ( ER). To assess the importance of PEMT localization for Hcy homeostasis, we identified and ablated the minimal ER targeting motif. Mutagenesis of a conserved, C-terminal lysine residue ( 197) relocalized the enzyme to the Golgi, demonstrating that Lys-197 is essential for targeting PEMT to the ER. To evaluate the functional significance of PEMT localization, hepatoma cell lines were generated that stably expressed either ER- or Golgi-localized PEMT only. Intriguingly, stable expression of PEMT in either the ER or the Golgi caused increased Hcy secretion. Moreover, PEMT-mediated Hcy secretion correlated with the methyltransferase activity of the enzyme, independently of subcellular localization. Thus, our data suggest that Hcy homeostasis is regulated concomitantly with PEMT activity but independently of PEMT localization.
• BIOSENSOR
  申请人：University Of Leeds

  公开号：EP2176654B1

  公开（公告）日：2017-03-22
• Method of Localizing Lipid Double Bonds
  申请人：MICROMASS UK LIMITED

  公开号：US20170047211A1

  公开（公告）日：2017-02-16

  A method of mass spectrometry for analysing lipids and similar biological molecules is disclosed. The lipid molecules may be ionised to form a plurality of lipid parent ions and subjected to photon-induced fragmentation to form a plurality of fragment or product ions. The position of one or more unsaturated bonds in the lipid molecules may be determined by mass analysing the fragment and product ions and analysing their intensity profile.
• US9724293B2
  申请人：——

  公开号：US9724293B2

  公开（公告）日：2017-08-08
• [EN] LIPOSOMAL FORMULATIONS, AND METHODS OF USING AND PREPARING THEREOF<br/>[FR] FORMULATIONS LIPOSOMALES ET LEURS PROCÉDÉS D'UTILISATION ET DE PRÉPARATION
  申请人：GLYCOMINE INC

  公开号：WO2020205530A1

  公开（公告）日：2020-10-08

  The disclosure provides phosphorylated carbohydrate replacement therapies (CRT) that include compositions of phosphorylated carbohydrates and phospholipids, as well as methods for preparing such compositions. Such compositions are suitable for pharmaceutical delivery of phosphorylated carbohydrates to cell interior, endoplasmic reticulum, and Golgi, and can be used for treating CDG type I and CDG type II diseases as well as other metabolic disorders.