1-octadecyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine | 86271-71-8

• 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: 1-octadecyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 86271-71-8
• 化学式: C46H86NO7P
• 分子量: 796.1
• InChiKey: GBNPCIWXLWZJGA-IGBSIYCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  55
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-hydroxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate 、 花生四烯酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以28 mg的产率得到1-octadecyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  10.3390/pharmaceutics16060762

  摘要：

  DOI：

  10.3390/pharmaceutics16060762

文献信息

• A Single Enzyme Catalyzes Both Platelet-activating Factor Production and Membrane Biogenesis of Inflammatory Cells
  作者：Hideo Shindou、Daisuke Hishikawa、Hiroki Nakanishi、Takeshi Harayama、Satoshi Ishii、Ryo Taguchi、Takao Shimizu

  DOI：10.1074/jbc.m609641200

  日期：2007.3

  Platelet-activating factor (PAF) is a potent proinflammatory lipid mediator eliciting a variety of cellular functions. Lipid mediators, including PAF are produced from membrane phospholipids by enzymatic cascades. Although a G protein-coupled PAF receptor and degradation enzymes have been cloned and characterized, the PAF biosynthetic enzyme, aceyl-CoAdyso-PAF acetyltransferase, has not been identified. Here, we cloned lyso-PAF acetyltransferase, which is critical in stimulus-dependent formation of PAF. The enzyme is a 60-kDa microsomal protein with three putative membrane-spanning domains. The enzyme was induced by bacterial endotoxin (lipopolysaccharide), which was suppressed by dexamethasone treatment. Surprisingly, the enzyme catalyzed not only biosynthesis of PAF from lyso-PAF but also incorporation of arachidonoyl-CoA to produce PAF precursor membrane glycerophospholipids (lysophosphatidylcholine acyltransferase activity). Under resting conditions, the enzyme prefers arachidonoyl-CoA and contributes to membrane biogenesis. Upon acute inflammatory stimulation with lipopolysaccharide, the activated enzyme utilizes acetyl-CoA more efficiently and produces PAF. Thus, our findings provide a novel concept that a single enzyme catalyzes membrane biogenesis of inflammatory cells while producing prophlogistic mediator in response to external stimuli.
• Orally administered peptides to ameliorate atherosclerosis
  申请人：The Regents of the University of California

  公开号：EP2198877B1

  公开（公告）日：2013-10-16
• 10.3390/pharmaceutics16060762
  作者：Kikuchi, Shuhei、Iwasaki, Yugo、Yoshioka, Mina、Hino, Kodai、Morita, Shin-Ya、Tada, Ryu、Uchimura, Yasuhiro、Kubo, Yoshinori、Kobayashi, Tomoya、Kinoshita, Yusuke、Hayashi, Masahiro、Furusho, Yoshio、Tamiaki, Hitoshi、Ishiyama, Hiroaki、Kuroda, Minoru、Udagawa, Jun

  DOI：10.3390/pharmaceutics16060762

  日期：——