1,2-己酰磷脂酰胆碱 | 53892-41-4

• 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-己酰磷脂酰胆碱
• 英文名称: Dicaproylphosphatidylcholine
• 英文别名: Dihexanoyl-lecithin；2,3-di(hexanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 53892-41-4
• 化学式: C₂₀H₄₀NO₈P
• 分子量: 453.513
• InChiKey: DVZARZBAWHITHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-己酰磷脂酰胆碱 在 phospholipase/lipase MPlaG 、 水 作用下， 以 aq. buffer 为溶剂， 反应 12.0h， 生成 2-hexanoyl-lysophosphatidylcholine
  参考文献：
  名称：

  NOVEL GENE DERIVED FROM MUD FLAT METAGENOME AND NOVEL PROTEIN OBTAINED THEREFROM SHOWING COACTIVITY OF PHOSPHOLIPASE AND LIPASE

  摘要：

  公开号：

  EP2784160B1
• 作为产物：
  描述：

  N-hexanoylimidazole 、 2,3-二羟丙基(2-(三甲基铵)乙基)磷酸酯 以 重水 、 乙腈 为溶剂， 反应 4.0h， 以36%的产率得到1,2-己酰磷脂酰胆碱
  参考文献：
  名称：

  水中核苷、核苷酸和甘油-3-磷酸胆碱的选择性酰化

  摘要：

  2',3'-二-O-乙酰基-核苷酸-5'-磷酸、2',3'-二-O-乙酰-核苷酸-5'-三磷酸和2',3',5的方便选择性合成'-tri-O-乙酰基-核苷在水中得到了开发。此外，还阐明了长链选择性甘油-3-磷酸胆碱二酰化。这些反应对环境无害、快速、收率高，并且产物易于纯化。重要的是，该反应可能表明关键代谢物的选择性酰化以促进它们并入原代谢中的益生元似是而非的反应途径。

  DOI：

  10.1055/s-0036-1588626
• 作为试剂：
  描述：

  在 乙二胺四乙酸 、 三羟甲基氨基甲烷盐酸盐 1,2-己酰磷脂酰胆碱 、 phosphoinositide-specific phospholipase C-δ1 、 calcium chloride 作用下， 以 重水 为溶剂， 生成 D-myo-Inositol-1,5-bisphosphate
  参考文献：
  名称：

  New aspects of formation of 1,2-cyclic phosphates by phospholipase C-δ1

  摘要：

  Phosphoinositide-specific phospholipase C-delta1 (PI-PLC-delta1) cleaves phosphatidylinositol 4,5-bisphosphate (PI-4,5-P-2, 1), 5-phosphate (PI-5-P, 2) and 4-phosphate (PI-4-P, 3) to form the mixture of the corresponding 4,5-, 5- and 4-phosphorylated inositol 1,2-cyclic phosphate (IcP) and 1-phosphate (IP) (4-6 and 7-9, respectively). In this work, we have studied the rates of the cleavage and the ratios of the cyclic-to-acyclic phosphate products under various pH and Ca2+ concentration conditions using P-31 NMR to monitor the reactions. In agreement with the previous report (Kim et al. Biochim. Biophys. Acta 1989, 163, 177), our results indicate that the IcP/IP ratios strongly depend on the reaction conditions, with the cyclic phosphate products formed predominantly at low pH (pH 5.0) and high calcium concentration (5 mM). Surprisingly, however, we have found that at pH 8.0 and 5 mM Ca2+, PI-5-P rather than PI-4,5-P2 is the most preferred substrate with the highest V-max. The cleavage of PI-5-P generated also more cyclic phosphate product than the other two substrates. In addition, we have studied the analogous reaction of phosphorothioate analogues of 1 with the sulfur placed in the nonbridging (10) or bridging (13) positions. We have found that the phosphorothioate analogue 10 produced exclusively the cyclic product 11, whereas the analogue 13 afforded exlusively the acyclic product 7. These results are discussed in terms of the mechanism of PI-PLC, where the cyclic product is formed by 'leaking' from the active site before its subsequent hydrolysis. The potential significance of the cyclic products in the signaling pathways is also discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00150-0

文献信息

• Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water
  作者：Matthew Powner、Christian Fernández-García

  DOI：10.1055/s-0036-1588626

  日期：——

  2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their

  2',3'-二-O-乙酰基-核苷酸-5'-磷酸、2',3'-二-O-乙酰-核苷酸-5'-三磷酸和2',3',5的方便选择性合成'-tri-O-乙酰基-核苷在水中得到了开发。此外，还阐明了长链选择性甘油-3-磷酸胆碱二酰化。这些反应对环境无害、快速、收率高，并且产物易于纯化。重要的是，该反应可能表明关键代谢物的选择性酰化以促进它们并入原代谢中的益生元似是而非的反应途径。
• NOVEL GENE DERIVED FROM MUD FLAT METAGENOME AND NOVEL PROTEIN OBTAINED THEREFROM SHOWING COACTIVITY OF PHOSPHOLIPASE AND LIPASE
  申请人：Korea Research Institute of Bioscience and Biotechnology

  公开号：EP2784160B1

  公开（公告）日：2016-01-13