sodium (2R,3R,4S,5S,6R)-4,5-dihydroxy-2-(((2R,3R,4S,5R,6R)-5-hydroxy-4-(((2S,4S,6S,8S,10R,12R,14R,16R,17R)-17-hydroxy-2,4,6,8,10,12,14,16-octamethyldotriacontanoyl)oxy)-6-(hydroxymethyl)-3-(palmitoyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl sulfate | 1456778-36-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: sodium (2R,3R,4S,5S,6R)-4,5-dihydroxy-2-(((2R,3R,4S,5R,6R)-5-hydroxy-4-(((2S,4S,6S,8S,10R,12R,14R,16R,17R)-17-hydroxy-2,4,6,8,10,12,14,16-octamethyldotriacontanoyl)oxy)-6-(hydroxymethyl)-3-(palmitoyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl sulfate
• CAS: 1456778-36-1
• 化学式: C₆₈H₁₂₉O₁₇S*Na
• 分子量: 1273.82
• InChiKey: VUBILPPMLGZEKJ-QIVKAJHXSA-M

反应信息

• 作为产物：
  描述：

  在 DOWEX Na⁺ ion-exchange column 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 以27.2 mg的产率得到sodium (2R,3R,4S,5S,6R)-4,5-dihydroxy-2-(((2R,3R,4S,5R,6R)-5-hydroxy-4-(((2S,4S,6S,8S,10R,12R,14R,16R,17R)-17-hydroxy-2,4,6,8,10,12,14,16-octamethyldotriacontanoyl)oxy)-6-(hydroxymethyl)-3-(palmitoyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl sulfate
  参考文献：
  名称：

  CD1b Tetramers Identify T Cells that Recognize Natural and Synthetic Diacylated Sulfoglycolipids from Mycobacterium tuberculosis

  摘要：

  Mycobacterial cell wall lipids bind the conserved CD1 family of antigen-presenting molecules and activate T cells via their T cell receptors (TCRs). Sulfoglycolipids (SGLs) are uniquely synthesized by Mycobacterium tuberculosis, but tools to study SGL-specific T cells in humans are lacking. We designed a novel hybrid synthesis of a naturally occurring SGL, generated CD1b tetramers loaded with natural or synthetic SGL analogs, and studied the molecular requirements for TCR binding and T cell activation. Two T cell lines derived using natural SGLs are activated by synthetic analogs independently of lipid chain length and hydroxylation, but differentially by saturation status. By contrast, two T cell lines derived using an unsaturated SGL synthetic analog were not activated by the natural antigen. Our data provide a bioequivalence hierarchy of synthetic SGL analogs and SGL-loaded CD1b tetramers. These reagents can now be applied to large-scale translational studies investigating the diagnostic potential of SGL-specific T cell responses or SGL-based vaccines.

  DOI：

  10.1016/j.chembiol.2018.01.006