[(2R,3R,4R,5R,6S)-6-[(2S,3S,4R)-2-(hexacosanoylamino)-3,4-dihydroxyoctadecoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] benzoate | 1309198-94-4

• 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: [(2R,3R,4R,5R,6S)-6-[(2S,3S,4R)-2-(hexacosanoylamino)-3,4-dihydroxyoctadecoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 1309198-94-4
• 化学式: C₅₇H₁₀₃NO₁₀
• 分子量: 962.446
• InChiKey: XBYXNZJOQBTXDN-NJXTZYGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.7
• 重原子数：
  68
• 可旋转键数：
  47
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 氢气 、 palladium(II) hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以18 mg的产率得到[(2R,3R,4R,5R,6S)-6-[(2S,3S,4R)-2-(hexacosanoylamino)-3,4-dihydroxyoctadecoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] benzoate
  参考文献：
  名称：

  Introduction of aromatic group on 4′-OH of α-GalCer manipulated NKT cell cytokine production

  摘要：

  The glycosphingolipid alpha-GalCer has been found to influence mammalian immune system significantly through the natural killer T cells. Unfortunately, the pre-clinical and clinical studies revealed several critical disadvantages that prevented the therapeutic application of alpha-GalCer in treating cancer and other diseases. Recently, the detailed illustration of the CD1d/alpha-GalCer/NKT TCR complex crystal structural, together with other latest structural and biological understanding on glycolipid ligands and NKT cells, provided a new platform for developing novel glycolipid ligands with optimized therapeutic effects. Here, we designed a series of novel aromatic group substituted alpha-GalCer analogues. The biological activity of these analogues was characterized and the results showed the unique substitution group manipulated the immune responses of NKT cells. Computer modeling and simulation study indicated the analogues had unique binding mode when forming CD1d/glycolipid/NKT TCR complex, comparing to original alpha-GalCer. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.11.061