1-O-α-D-galactopyranosyl-2-N-(11-tetradecylselenoundecanoyl)-2S,3S,4R-phytosphingosine

• 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-α-D-galactopyranosyl-2-N-(11-tetradecylselenoundecanoyl)-2S,3S,4R-phytosphingosine
• 英文别名: N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-11-tetradecylselanylundecanamide
• 化学式: C₄₉H₉₇NO₉Se
• 分子量: 923.27
• InChiKey: JPXXCFIDRBZHGI-XAPODPEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.85
• 重原子数：
  60
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 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：

  糖脂 在 N-甲基吗啉 、 copper(ll) sulfate pentahydrate 、 硫酸 、 triflic azide 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 silver trifluoromethanesulfonate 、 sodium hydride 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 36.0h， 生成 1-O-α-D-galactopyranosyl-2-N-(11-tetradecylselenoundecanoyl)-2S,3S,4R-phytosphingosine
  参考文献：
  名称：

  Synthesis and Th1-immunostimulatory activity of α-galactosylceramide analogues bearing a halogen-containing or selenium-containing acyl chain

  摘要：

  A novel series of CD1d ligand alpha-galactosylceramides (alpha-GalCers) were synthesized by incorporation of the heavy atoms Br and Se in the acyl chain backbone of alpha-galactosyl-N-cerotoylphytosphingosine. The synthetic analogues are potent CD1d ligands and stimulate mouse invariant natural killer T (iNKT) cells to selectively enhance Th1 cytokine production. These synthetic analogues would be efficient X-ray crystallographic probes to disclose precise atomic positions of alkyl carbons and lipid-protein interactions in KRN7000/CD1d complexes. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.06.007

文献信息

• Synthesis and Th1-immunostimulatory activity of α-galactosylceramide analogues bearing a halogen-containing or selenium-containing acyl chain
  作者：Md. Imran Hossain、Shinya Hanashima、Takuto Nomura、Sébastien Lethu、Hiroshi Tsuchikawa、Michio Murata、Hiroki Kusaka、Shunsuke Kita、Katsumi Maenaka

  DOI：10.1016/j.bmc.2016.06.007

  日期：2016.8

  A novel series of CD1d ligand alpha-galactosylceramides (alpha-GalCers) were synthesized by incorporation of the heavy atoms Br and Se in the acyl chain backbone of alpha-galactosyl-N-cerotoylphytosphingosine. The synthetic analogues are potent CD1d ligands and stimulate mouse invariant natural killer T (iNKT) cells to selectively enhance Th1 cytokine production. These synthetic analogues would be efficient X-ray crystallographic probes to disclose precise atomic positions of alkyl carbons and lipid-protein interactions in KRN7000/CD1d complexes. (C) 2016 Elsevier Ltd. All rights reserved.