1-棕榈酰基-sn-甘油-3-磷酸钠盐 | 7220-34-0

• 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-sn-甘油-3-磷酸钠盐
• 英文名称: 16:0 LPA
• 英文别名: 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphate；1-palmitoyl lysophosphatidic acid；lysophosphatidic acid；1-O-Palmitoyl-L-glycerin-3-phosphat；(2R)-2-hydroxy-3-(phosphonooxy)propyl hexadecanoate；[(2R)-2-hydroxy-3-phosphonooxypropyl] hexadecanoate
• CAS: 7220-34-0
• 化学式: C₁₉H₃₉O₇P
• 分子量: 410.488
• InChiKey: YNDYKPRNFWPPFU-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-棕榈酰基-sn-甘油-3-磷酸钠盐 在 Tris buffer 、 水 、 sodium chloride 作用下， 生成 2-油酰-1-棕榈锡甘油-3-磷酸胆碱
  参考文献：
  名称：

  Liposome-mediated enzymatic synthesis of phosphatidylcholine as an approach to self-replicating liposomes

  摘要：

  The four enzymes of the salvage pathway for phosphatidylcholine synthesis sn-glycerol-3-phosphate acyltransferase, 1-acyl-sn-glycerol-3-phosphate acyltransferase, phosphatidate phosphatase, and cytidinediphosphocholine phosphocholinetransferase were simulataneously bound to soybean phosphatidylcholine liposomes. Evidence is presented that the entire enzyme chain is reconstituted in the liposomes, and that synthesis is preferentially localized in the proteliposomal membrane where the enzymes are present in an active bound form. Various phosphatidylcholines, differing in the alkyl group of the fatty acid moieties, can be synthesized in this way and incorporated into the host liposomes, with a corresponding change of the equilibrium size of the liposomes. The present system can then also be seen as a self-reproducing liposome, and the implication of this for chemical autopoiesis is briefly discussed.

  DOI：

  10.1021/ja00021a043
• 作为产物：
  描述：

  1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-glycerol 在 四氮唑 、 盐酸 、 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 反应 64.0h， 生成 1-棕榈酰基-sn-甘油-3-磷酸钠盐
  参考文献：
  名称：

  A new approach to the synthesis of lysophospholipids: preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate

  摘要：

  A new stereospecific synthesis of lysophosphatidic acid and lysophosphatidylcholine is reported. The sequence relies on p-nitrophenyl-D-glycerate as a chiral synthon, including chemoselective reduction of the active ester function without affecting other carboxylic ester groups present in the molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.161

文献信息

• Synthesis of phosphatidic acids <i>via</i> cobalt(salen) catalyzed epoxide ring-opening with dibenzyl phosphate
  作者：Ruben L. H. Andringa、Marijn Jonker、Adriaan J. Minnaard

  DOI：10.1039/d2ob00168c

  日期：——

  With a CoIII(salen)OTs catalyst, dibenzyl phosphate ring-opens a variety of terminal epoxides with excellent regio-selectively and yields up to 85%. The reaction is used in a highly efficient synthesis of enantiopure mixed-diacyl phosphatidic acids, including a photoswitchable phosphatidic acid mimic.

  在 CoIII(salen)OTs 催化剂的作用下，磷酸二苄酯能够以优异的区域选择性对多种末端环氧化物进行开环，收率高达 85%。该反应用于高效合成对映体纯混合二酰基磷脂酸，包括光可切换磷脂酸模拟物。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Efficient Synthesis of Phospholipids from Glycidyl Phosphates
  作者：Jan Lindberg、Johan Ekeroth、Peter Konradsson

  DOI：10.1021/jo010734+

  日期：2002.1.1

  New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O-palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.
• Stoffel,W.; Wolf,G.D., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1966, vol. 347, p. 94 - 101
  作者：Stoffel,W.、Wolf,G.D.

  DOI：——

  日期：——
• Cost-Effective and Large-Scale Synthesis of 16:0 Lysophosphatidic Acid
  作者：James E. East、Timothy L. Macdonald

  DOI：10.1080/00397911.2011.587080

  日期：2012.12.15

  Lysophosphatidic acid (LPA) is a bioactive compound that has gained attention because of its role in neoplastic diseases. Popularity of the compound has necessitated the use of large quantities of the phospholipid for in vivo and in vitro testing, but methods for generating LPA require the use of costly procedures, namely phosphoramidite coupling reagents. Additionally there has been no reported large-scale synthesis of LPA. In the present study we report the cost-effective and large-scale synthesis of 16: 0 LPA.