N-myristoylcerebroside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: N-myristoylcerebroside
• 英文别名: N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]tetradecanamide
• 化学式: C₃₈H₇₃NO₈
• 分子量: 672.0
• InChiKey: BDGGMKFFYWPIFU-BSUUUAJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  47
• 可旋转键数：
  31
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  肉豆蔻酸 、 神经鞘氨醇半乳糖苷 在 三乙胺 、 氯甲酸丁酯 作用下， 以 四氢呋喃 、 乙腈 、 甲醇 为溶剂， 反应 2.33h， 以60%的产率得到N-myristoylcerebroside
  参考文献：
  名称：

  Iron-mediated free-radical formation of signaling lipids in a model system

  摘要：

  It has been shown using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and its combination with thin-layer chromatography (TLC) that the action of the ascorbate/Fe2+/H2O2 oxidizing system on cardiolipin and galactocerebroside results in the formation of phosphatidic acid (PA) and ceramide (Cer), respectively. These data, when combined with results obtained on radiolysis of similar substances, allowed the conclusion that the formation of PA and Cer occurs via an OH-induced fragmentation taking place in polar moiety of the starting substrates. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.06.002

文献信息

• Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells
  作者：Jin Park、Qian Li、Young-Tae Chang、Tae Sung Kim

  DOI：10.1016/j.bmc.2005.01.027

  日期：2005.4

  Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4(+) T cells, is an important stimulus for the switch of the antibody isotype to IgE in both mice and humans. In this study we investigated the inhibitory activity of IL-4 production in activated T cells by screening ceramide derivatives prepared by solid phase combinatorial chemistry. Many ceramide derivatives significantly inhibited IL-4 production in T cells. In particular, ceramide derivatives with a lauroyl group showed strong inhibitory activities on IL-4 production in both phorbol 12-myristate 13-acetate (PMA)-activated EL4 T cells and antigen-primed cells, suggesting that they can be used as compounds for the development of anti-allergic agents. (c) 2005 Elsevier Ltd. All rights reserved.
• The Synthesis and Biological Characterization of a Ceramide Library
  作者：Young-Tae Chang、Jaehwa Choi、Sheng Ding、Eva E. Prieschl、Thomas Baumruker、Jae-Mok Lee、Sung-Kee Chung、Peter G. Schultz

  DOI：10.1021/ja017576o

  日期：2002.3.1

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.
• Iron-mediated free-radical formation of signaling lipids in a model system
  作者：Irina Yurkova、Mikhail Kisel、Juergen Arnhold、Oleg Shadyro

  DOI：10.1016/j.chemphyslip.2005.06.002

  日期：2005.10

  It has been shown using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and its combination with thin-layer chromatography (TLC) that the action of the ascorbate/Fe2+/H2O2 oxidizing system on cardiolipin and galactocerebroside results in the formation of phosphatidic acid (PA) and ceramide (Cer), respectively. These data, when combined with results obtained on radiolysis of similar substances, allowed the conclusion that the formation of PA and Cer occurs via an OH-induced fragmentation taking place in polar moiety of the starting substrates. (c) 2005 Elsevier Ireland Ltd. All rights reserved.