1-O-(alpha-D-glucopyranosyl)-N-icosa-11,14-dienoylphytosphingosine | 952091-26-8

• 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: 1-O-(alpha-D-glucopyranosyl)-N-icosa-11,14-dienoylphytosphingosine
• 英文别名: (11Z,14Z)-N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]icosa-11,14-dienamide
• CAS: 952091-26-8
• 化学式: C₄₄H₈₃NO₉
• 分子量: 770.144
• InChiKey: WSXMIFGRYXQZQZ-ZIAYHSIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  54
• 可旋转键数：
  36
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,3R,4S,5S,6R)-2-(((2S,3S,4R)-2-amino-3,4-dihydroxyoctadecyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 、 11,14-eicosadienoyl chloride 在 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以66%的产率得到1-O-(alpha-D-glucopyranosyl)-N-icosa-11,14-dienoylphytosphingosine
  参考文献：
  名称：

  Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides

  摘要：

  alpha-Glucosyl ceramides 4 and 5 have been synthesised and evaluated for their ability to stimulate the activation and expansion of human iNKT cells. The key challenge in the synthesis of both target molecules was the stereoselective synthesis of the alpha-glycosidic linkage. Of the methods examined, glycosylation using per-TMS-protected glucosyl iodide 16 was completely alpha-selective and provided gram quantities of amine 11, from which alpha-glucosyl ceramides 4 and 5 were obtained by N-acylation. alpha-GlcCer 4, containing a C24 saturated acyl chain, stimulated a marked proliferation and expansion of human circulating iNKT cells in short-term cultures. alpha-GlcCer 5, which contains a C20 11,14-cis-diene acyl chain (C20: 2), induced extremely similar levels of iNKT cell activation and expansion. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.010

文献信息

• Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides
  作者：Peter J. Jervis、Natacha Veerapen、Gabriel Bricard、Liam R. Cox、Steven A. Porcelli、Gurdyal S. Besra

  DOI：10.1016/j.bmcl.2010.05.010

  日期：2010.6

  alpha-Glucosyl ceramides 4 and 5 have been synthesised and evaluated for their ability to stimulate the activation and expansion of human iNKT cells. The key challenge in the synthesis of both target molecules was the stereoselective synthesis of the alpha-glycosidic linkage. Of the methods examined, glycosylation using per-TMS-protected glucosyl iodide 16 was completely alpha-selective and provided gram quantities of amine 11, from which alpha-glucosyl ceramides 4 and 5 were obtained by N-acylation. alpha-GlcCer 4, containing a C24 saturated acyl chain, stimulated a marked proliferation and expansion of human circulating iNKT cells in short-term cultures. alpha-GlcCer 5, which contains a C20 11,14-cis-diene acyl chain (C20: 2), induced extremely similar levels of iNKT cell activation and expansion. (C) 2010 Elsevier Ltd. All rights reserved.