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.
• Synthesis of ganglioside epitopes for oligosaccharide specific immunoadsorption therapy of Guillian-Barré syndrome
  作者：Søren M. Andersen、Chang-Chun Ling、Ping Zhang、Kate Townson、Hugh J. Willison、David R. Bundle

  DOI：10.1039/b400029c

  日期：——

  Guillain-Barré syndrome is a postinfectious, autoimmune neuropathy resulting in neuromuscular paralysis. Auto-antibodies, often induced by bacterial infection, bind to human gangliosides possessing monosialoside and diasialoside epitopes and impair the function of nerve junctions, where these ganglioside structures are highly enriched. Truncated gangliosides representive of GD3, GQ1b and GM2 epitopes have been synthesized as methyl glycosides and as a glycosides of an eleven carbon tether. The synthetic oligosaccharide ligands are structural mimics of these highly complex ganglioside epitopes and via their ability to neutralize or remove auto-antibodies have the potential for therapy, either as soluble blocking ligands administered systemically, or as immuno-affinity ligands for use as extracorporeal immunoadsorbents.

  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。