(2-O-arachidyl-3-O-stearyl-sn-glycer-1-yl) β-D-glucopyranosyl phosphate sodium salt | 1037195-64-4

• 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: (2-O-arachidyl-3-O-stearyl-sn-glycer-1-yl) β-D-glucopyranosyl phosphate sodium salt
• 英文别名: sodium;[(2S)-2-icosanoyloxy-3-octadecanoyloxypropyl] [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate
• CAS: 1037195-64-4
• 化学式: C₄₇H₉₀O₁₃P*Na
• 分子量: 917.187
• InChiKey: ZBAFLTQEUDCKOP-VLKLTMECSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  62
• 可旋转键数：
  45
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  (2-O-arachidyl-3-O-stearyl-sn-glycer-1-yl) (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phosphate triethylammonium salt 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.08h， 以3.0 mg的产率得到(2-O-arachidyl-3-O-stearyl-sn-glycer-1-yl) β-D-glucopyranosyl phosphate sodium salt
  参考文献：
  名称：

  Syntheses of phosphatidyl-β-d-glucoside analogues to probe antigen selectivity of monoclonal antibody ‘DIM21’

  摘要：

  Herein, we report the chemical syntheses of a series of phosphatidyl-beta-D-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, beta-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody 'DIM21' (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.041

文献信息

• First synthesis of natural phosphatidyl-β-d-glucoside
  作者：Peter Greimel、Yukishige Ito

  DOI：10.1016/j.tetlet.2008.04.036

  日期：2008.5

  Herein, we report the chemical synthesis of naturally occurring mammalian phosphatidyl-β-d-glucoside (PtdGlc), in order to confirm the proposed structure and to clarify its stereochemistry. We designed a convergent synthetic strategy, suitable to prepare sensitive PtdGlc derivatives. As an initial demonstration of our strategy, we successfully prepared both PtdGlc diastereomers as well as its sensitive

  本文中，我们报告了天然存在的哺乳动物磷脂酰-β-d-葡萄糖苷（PtdGlc）的化学合成，以确认所提出的结构并阐明其立体化学。我们设计了一种收敛的合成策略，适用于制备敏感的PtdGlc衍生物。作为我们策略的初步证明，我们成功制备了PtdGlc非对映异构体及其敏感的花生四烯酸类似物。证实了天然样品中两种非对映异构体的存在。
• Syntheses of phosphatidyl-β-d-glucoside analogues to probe antigen selectivity of monoclonal antibody ‘DIM21’
  作者：Peter Greimel、Milaine Lapeyre、Yasuko Nagatsuka、Yoshio Hirabayashi、Yukishige Ito

  DOI：10.1016/j.bmc.2008.06.041

  日期：2008.8

  Herein, we report the chemical syntheses of a series of phosphatidyl-beta-D-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, beta-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody 'DIM21' (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding. (C) 2008 Elsevier Ltd. All rights reserved.