methyl O-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2->8)-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2->8)-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
• 英文别名: NeuAc(a2-8)NeuAc(a2-3)Gal(b1-4)b-Glc1Me；(2S,4S,5R,6R)-5-acetamido-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxyoxane-2-carboxylic acid
• 化学式: C₃₅H₅₈N₂O₂₇
• 分子量: 938.843
• InChiKey: GHSQZLNIUFDAOR-JXAFKSDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.1
• 重原子数：
  64
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  470
• 氢给体数：
  17
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以9.2 mg的产率得到methyl O-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid]-(2->8)-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ganglioside epitopes for oligosaccharide specific immunoadsorption therapy of Guillian-Barré syndrome

  摘要：

  吉兰-巴雷综合征是一种感染后自身免疫性神经病，会导致神经肌肉麻痹。自身抗体通常由细菌感染诱导，与具有单神经节苷脂和二神经节苷脂表位的人类神经节苷脂结合，损害神经连接的功能，而这些神经节苷脂结构在神经连接中高度富集。代表 GD3、GQ1b 和 GM2 表位的截短神经节苷脂已被合成为甲基糖苷和 11 个碳系的糖苷。合成的寡糖配体是这些高度复杂的神经节苷脂表位的结构模拟物，通过其中和或清除自身抗体的能力，具有治疗的潜力，既可以作为全身给药的可溶性阻断配体，也可以作为体外免疫吸附剂使用的免疫亲和配体。

  DOI：

  10.1039/b400029c

文献信息

• Two-Step Chemoenzymatic Detection of <i>N</i>-Acetylneuraminic Acid−α(2-3)-Galactose Glycans
  作者：Liuqing Wen、Yuan Zheng、Kuan Jiang、Mingzhen Zhang、Shukkoor Muhammed Kondengaden、Shanshan Li、Kenneth Huang、Jing Li、Jing Song、Peng George Wang

  DOI：10.1021/jacs.6b07132

  日期：2016.9.14

  Sialic acids are typically linked alpha(2-3) or alpha(2-6) to the galactose that located at the non-reducing terminal end of glycans, playing important but distinct roles in a variety of biological and pathological processes. However, details about their respective roles are still largely unknown due to the lack of an effective analytical technique. Herein, a two-step chemoenzymatic approach for the rapid and sensitive detection of N-acetylneuraminic acid-alpha(2-3)-galactose glycans is described.