(R)-(-)-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine | 97802-53-4

• 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: (R)-(-)-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine
• 英文别名: 1-(1Z-hexadecenyl)-sn-glycero-3-phosphocholine；lysoplasmenylcholine；1-(1-enyl-palmitoyl)-GPC(P-16:0)；pLPC；LysoPC(P-16:0/0:0)；[(2R)-3-[(Z)-hexadec-1-enoxy]-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 97802-53-4
• 化学式: C₂₄H₅₀NO₆P
• 分子量: 479.638
• InChiKey: HTZINLFNXLXRBC-CQLBIITFSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  棕榈酸酐 、 (R)-(-)-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到(R)-(-)-2-hexadecanoyl-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine
  参考文献：
  名称：

  Direct Synthesis of Plasmenylcholine from Allyl-Substituted Glycerols

  摘要：

  We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxyprotected 1-allylglycerol precursors with s-BuLi at -65 to -80degreesC. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.

  DOI：

  10.1021/jo026826w
• 作为产物：
  描述：

  (S)-1-(allyloxy)propane-2,3-diol 在 咪唑 、 四丁基氟化铵 、 仲丁基锂 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 环己烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 49.25h， 生成 (R)-(-)-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine
  参考文献：
  名称：

  Direct Synthesis of Plasmenylcholine from Allyl-Substituted Glycerols

  摘要：

  We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxyprotected 1-allylglycerol precursors with s-BuLi at -65 to -80degreesC. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.

  DOI：

  10.1021/jo026826w

文献信息

• The Highly Selective Production of 2-Arachidonoyl Lysophosphatidylcholine Catalyzed by Purified Calcium-independent Phospholipase A2γ
  作者：Wei Yan、Christopher M. Jenkins、Xianlin Han、David J. Mancuso、Harold F. Sims、Kui Yang、Richard W. Gross

  DOI：10.1074/jbc.m502358200

  日期：2005.7

  Herein, we report the heterologous expression of the human peroxisomal 63-kDa calcium-independent phospholipase A(2)gamma (iPLA(2)gamma) isoform in Sf9 cells, purification of the N-terminal His-tagged enzyme by affinity chromatography, and the identification of its remarkable substrate selectivity that results in the highly selective generation of 2-arachidonoyl lysophosphatidylcholine. Mass spectrometric analyses demonstrated that purified iPLA(2)gamma hydrolyzed saturated or monounsaturated aliphatic groups readily from either the sn-1 or sn-2 positions of phospholipids. In addition, purified iPLA(2)gamma effectively liberated arachidonic acid from the sn-2 position of plasmenylcholine substrates. In contrast, incubation of iPLA(2)gamma with 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine resulted in the rapid release of palmitic acid and the selective accumulation of 2-arachidonoyl lysophosphatidylcholine (LPC), which was not metabolized further by iPLA(2)gamma. The putative regiospecificity of the 2-arachidonoyl LPC product was authenticated by its diagnostic fragmentation pattern during tandem mass spectrometric analysis. To identify the physiological relevance of iPLA(2)gamma-mediated 2-arachidonoyl LPC production utilizing naturally occurring membranes, we incubated purified rat hepatic peroxisomes with iPLA(2)gamma and similarly identified the selective accumulation of 2-arachidonoyl LPC. Furthermore, tandem mass spectrometric analysis demonstrated that 2-arachidonoyl LPC is a natural product in human myocardium, a tissue in which iPLA(2)gamma expression is robust. Because 2-arachidonoyl LPC represents a key branch point intermediate that can potentially lead to a variety of bioactive molecules in eicosanoid signaling (e.g. arachidonic acid, 2-arachidonoylglycerol), these results have uncovered a novel eicosanoid selective pathway through iPLA(2)gamma-mediated 2-arachidonoyl LPC production to amplify and diversify the repertoire of biologic lipid second messengers in response to cellular stimulation.
• The Genomic Organization, Complete mRNA Sequence, Cloning, and Expression of a Novel Human Intracellular Membrane-associated Calcium-independent Phospholipase A2
  作者：David J. Mancuso、Christopher M. Jenkins、Richard W. Gross

  DOI：10.1074/jbc.275.14.9937

  日期：2000.4

  During the sequencing of the long arm of chromosome 7 in the Human Genome Project, a predicted protein product of 40 kDa was identified, which contained two similar to 10-amino acid segments homologous to the ATP and lipase consensus sequences present in the founding members of a family of calcium-independent phospholipases A(2). Detailed inspection of the identified sequence (residues 79,671-109,912 GenBank(TM) accession no. AC005058) demonstrated that it represented only a partial sequence of a larger undefined polypeptide product. Accordingly, we identified the complete genomic organization of this putative phospholipase A, through analyses of previously published expressed sequence tags, PCR of human heart cDNA, and 5'-rapid amplification of cDNA ends. Polymerase chain reaction and Northern blotting demonstrated a 3.4-kilobase message, which encoded a polypeptide with a maximum calculated molecular weight of 88476.9, This 3,4-kilobase message was present in multiple human parenchymal tissues including heart, skeletal muscle, placenta, brain, liver, and pancreas. Cloning and expression of the protein encoded by this message in Sf9 cells resulted in the production of two proteins of apparent molecular masses of 77 and 63 kDa as assessed by Western analyses utilizing immunoaffinity-purified antibody. Membranes from Sf9 cells expressing recombinant protein released fatty acid from sn-2-radiolabeled phosphatidylcholine and plasmenylcholine up to 10-fold more rapidly than controls. The initial rate of fatty acid release from the membrane fraction was 0.3 nmol/mg min. The recombinant protein was entirely calcium-independent, had a pH optimum of 8.0, was inhibited by (E)-6-(bromomethylene)-3-(1-naphthalenyl)-2H-tetrahydropyran (IC50 = 3 mu M), and was predominantly present in the membrane-associated fraction. Collectively, these results describe the genomic organization, complete mRNA sequence, and sn-a-lipase activity of a novel intracellular calcium-independent membrane-associated phospholipase A(2).
• IN VITRO VERFAHREN ZUR ERKENNUNG UND DIAGNOSTIK AKUTER KORONARER SYNDROME
  申请人：Frei, Ulrich

  公开号：EP1104547A1

  公开（公告）日：2001-06-06
• US5277913A
  申请人：——

  公开号：US5277913A

  公开（公告）日：1994-01-11
• US7294496B1
  申请人：——

  公开号：US7294496B1

  公开（公告）日：2007-11-13