(2S,3R,4E)-2-Azido-3-(pivaloyloxy)-4-octadecen-1-ol | 114275-43-3

• 分子结构分类: 有机化合物
• 英文名称: (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-4-octadecen-1-ol
• 英文别名: [(E,2S,3R)-2-azido-1-hydroxyoctadec-4-en-3-yl] 2,2-dimethylpropanoate
• CAS: 114275-43-3
• 化学式: C₂₃H₄₃N₃O₃
• 分子量: 409.613
• InChiKey: HZMLWZSBRDXJTC-BWMVHVDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  29.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  95.29
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2,6-di-O-pivaloyl-α-D-glucopyranosyl) trichloroacetimidate 、 (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-4-octadecen-1-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以83%的产率得到O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2,6-di-O-pivaloyl-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-azido-3-O-pivaloyl-4-octadecene-1,3-diol
  参考文献：
  名称：

  N-修饰的神经节苷脂GM3衍生物的合成

  摘要：

  神经节苷脂GM3及其衍生物具有许多重要的生物学功能。使用亚磷酸二乙酯保护的唾液酸作为糖基供体，并用3,2'，3'，4'-未保护的乳糖作为糖基受体，以优异的异头立体选择性组装了含唾液酸的三糖。将该三糖进一步与神经酰胺前体偶联以产生鞘氨醇1。基于该关键中间体，顺利合成了唾液酸残基的氮或神经酰胺部分的氮具有修饰的两个不同系列的N-修饰的GM3类似物和GM3本身。

  DOI：

  10.1016/j.tet.2011.12.019
• 作为产物：
  描述：

  <2(S),3(R),4E>-2-azido-1,3-O-isopropylidene-4-octadecene-1,3-diol 在 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 113.0h， 生成 (2S,3R,4E)-2-Azido-3-(pivaloyloxy)-4-octadecen-1-ol
  参考文献：
  名称：

  Zimmermann, Peter; Schmidt, Richard R., Liebigs Annalen der Chemie, 1988, p. 663 - 668

  摘要：

  DOI：

文献信息

• Influence of Gb3 glycosphingolipids differing in their fatty acid chain on the phase behaviour of solid supported membranes: chemical syntheses and impact of Shiga toxin binding
  作者：Ole M. Schütte、Annika Ries、Alexander Orth、Lukas J. Patalag、Winfried Römer、Claudia Steinem、Daniel B. Werz

  DOI：10.1039/c4sc01290a

  日期：——

  The Shiga toxin B subunit (STxB), which is involved in cell membrane attachment and trafficking of Shiga holotoxin, binds specifically to the glycosphingolipid Gb3. In biological membranes, Gb3 glycosphingolipids differ in their fatty acid composition and there is strong evidence that the fatty acid alters the binding behaviour of STxB as well as the intracellular routing of the Shiga toxin/Gb3 complex. To analyse the binding of STxB to different Gb3s, we chemically synthesized saturated, unsaturated, α-hydroxylated Gb3s and a combination thereof, all based on a C24-fatty acid chain starting from monosaccharide building blocks, sphingosine and the respective fatty acids. These chemically well-defined Gb3s were inserted into solid supported phase-separated lipid bilayers composed of DOPC/sphingomyelin/cholesterol as a simple mimetic of the outer leaflet of animal cell membranes. By fluorescence- and atomic force microscopy the phase behaviour of the bilayer as well as the lateral organization of bound STxB were analysed. The fatty acid of Gb3 significantly alters the ratio between the ordered and disordered phase and induces a third intermediate phase in the presence of unsaturated Gb3. The lateral organization of STxB on the membranes varies significantly. While STxB attached to membranes with Gb3s with saturated fatty acids forms protein clusters, it is more homogeneously bound to membranes containing unsaturated Gb3s. Large interphase lipid redistribution is observed for α-hydroxylated Gb3 doped membranes. Our results clearly demonstrate that the fatty acid of Gb3 strongly influences the lateral organization of STxB on the membrane and impacts the overall membrane organization of phase-separated lipid membranes.

  志贺毒素B亚基（STxB）参与细胞膜附着和志贺毒素的转运，特异性地结合到糖神经酰胺Gb3上。在生物膜中，Gb3糖神经酰胺的脂肪酸组成不同，有强有力的证据表明脂肪酸改变STxB的结合行为以及志贺毒素/Gb3复合物的细胞内运输途径。为了分析STxB与不同Gb3的结合，我们化学合成了饱和、不饱和、α-羟基化的Gb3及其组合，所有这些都基于从单糖构建块、鞘氨醇和相应的脂肪酸开始的C24脂肪酸链。这些化学上定义明确的Gb3被插入到由DOPC/鞘磷脂/胆固醇组成的固相分离脂质双层中，作为动物细胞膜外叶的简单模拟物。通过荧光显微镜和原子力显微镜分析了双层的相行为以及STxB结合的侧向组织。Gb3的脂肪酸显著改变了有序和无序相的比例，并在存在不饱和Gb3的情况下诱导了第三种中间相。STxB在膜上的侧向组织显著变化。当STxB附着在含有饱和脂肪酸Gb3的膜上时形成蛋白质簇，它更均匀地结合到含有不饱和Gb3的膜上。观察到α-羟基化Gb3掺杂膜的大相间脂质重分布。我们的结果清楚地表明，Gb3的脂肪酸强烈影响STxB在膜上的侧向组织，并影响相分离脂质膜的整体膜组织。
• Synthesis of Gb ₃ Glycosphingolipids with Labeled Head Groups: Distribution in Phase‐Separated Giant Unilamellar Vesicles
  作者：Jeremias Sibold、Katharina Kettelhoit、Loan Vuong、Fangyuan Liu、Daniel B. Werz、Claudia Steinem

  DOI：10.1002/anie.201910148

  日期：2019.12.2

  sphingosine backbone. The synthetic Gb3 glycosphingolipids were reconstituted into coexisting liquid-ordered (lo )/liquid-disordered (ld ) giant unilamellar vesicles (GUVs), and STx binding was verified by fluorescence microscopy. Gb3 with the C24:0 fatty acid partitioned mostly in the lo phase, while the unsaturated C24:1 fatty acid distributes more into the ld phase. The α-hydroxylation does not influence

  受体脂质Gb3负责将志贺毒素（STx）特异性内化到细胞中。Gb3的头基定义了STx结合的特异性，并且具有不同脂肪酸的主链有望影响其在膜内的定位，从而影响膜的组织和蛋白质的内在化。为了研究这种影响，合成了一组标有BODIPY荧光团标记在头部基团上的Gb3糖鞘脂。将C24脂肪酸，饱和的，不饱和的，α-羟基化的衍生物及其组合连接至鞘氨醇主链。合成的Gb3糖鞘脂被重构为共存的液体有序（lo）/液体无序（ld）巨型单层囊泡（GUVs），并通过荧光显微镜验证了STx的结合。带有C24的Gb3：0脂肪酸主要在lo相中分配，而不饱和C24：1脂肪酸则更多地分配到ld相中。α-羟基化不影响其分配。
• ZIMMERMANN, PETER;BOMMER, RENE;BAR, THOMAS;SCHMIDT, RICHARD R., J. CARBOHYDR. CHEM., 7,(1988) N 12, 435-452
  作者：ZIMMERMANN, PETER、BOMMER, RENE、BAR, THOMAS、SCHMIDT, RICHARD R.

  DOI：——

  日期：——
• ZIMMERMANN, PETER;SCHMIDT, RICHARD R., LIEBIGS ANN. CHEM.,(1988) N 7, 663-667
  作者：ZIMMERMANN, PETER、SCHMIDT, RICHARD R.

  DOI：——

  日期：——