ethyl [methyl(3-O-acetyl-2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]-(1->3)-2,4,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside | 1352813-72-9

• 分子结构分类: 有机化合物
• 英文名称: ethyl [methyl(3-O-acetyl-2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]-(1->3)-2,4,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside
• CAS: 1352813-72-9
• 化学式: C₅₂H₄₈O₁₇S
• 分子量: 977.009
• InChiKey: DWWUQSMPJHWURC-VMEQMFCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  70.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-β-D-glucopyranoside 、 ethyl [methyl(3-O-acetyl-2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]-(1->3)-2,4,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到2-azidoethyl [methyl(3-O-acetyl-2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]-(1->3)-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Molecular Recognition Studies of the HNK-1 Trisaccharide and Related Oligosaccharides. The Specificity of Monoclonal Anti-HNK-1 Antibodies as Assessed by Surface Plasmon Resonance and STD NMR

  摘要：

  The human natural killer cell carbohydrate, HNK-1, plays function-conducive roles in peripheral nerve regeneration and synaptic plasticity. It is also the target of autoantibodies in polyneuropathies. It is thus important to synthesize structurally related HNK-1 carbohydrates for optimizing its function-conducive roles, and for diagnosis and neutralization of autoantibodies in the fatal Guillain-Barre syndrome. As a first step toward these goals, we have synthesized several HNK-1 carbohydrate derivatives to assess the specificity of monoclonal HNK-1 antibodies from rodents: 2-aminoethyl glycosides of selectively O-sulfated trisaccharide corresponding to the HNK-1 antigen, its nonsulfated analogue, and modified structures containing 3-O-fucosyl or 6-O-sulfo substituents in the N-acetylglucosamine residues. These were converted, together with several related oligosaccharides, into biotin-tagged probes to analyze the precise carbohydrate specificity of two anti-HNK-1 antibodies by surface plasmon resonance that revealed a crucial role of the glucuronic acid in antibody binding. The contribution of the different oligosaccharide moieties in the interaction was shown by saturation transfer difference (STD) NMR of the complex consisting of the HNK-1 pentasaccharide and the HNK-1 412 antibody.

  DOI：

  10.1021/ja2083015
• 作为产物：
  描述：

  [methyl(3-O-acetyl-2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]-(1->3)-2,4,6-tri-O-benzoyl-D-galactopyranose 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl [methyl(3-O-acetyl-2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]-(1->3)-2,4,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Molecular Recognition Studies of the HNK-1 Trisaccharide and Related Oligosaccharides. The Specificity of Monoclonal Anti-HNK-1 Antibodies as Assessed by Surface Plasmon Resonance and STD NMR

  摘要：

  The human natural killer cell carbohydrate, HNK-1, plays function-conducive roles in peripheral nerve regeneration and synaptic plasticity. It is also the target of autoantibodies in polyneuropathies. It is thus important to synthesize structurally related HNK-1 carbohydrates for optimizing its function-conducive roles, and for diagnosis and neutralization of autoantibodies in the fatal Guillain-Barre syndrome. As a first step toward these goals, we have synthesized several HNK-1 carbohydrate derivatives to assess the specificity of monoclonal HNK-1 antibodies from rodents: 2-aminoethyl glycosides of selectively O-sulfated trisaccharide corresponding to the HNK-1 antigen, its nonsulfated analogue, and modified structures containing 3-O-fucosyl or 6-O-sulfo substituents in the N-acetylglucosamine residues. These were converted, together with several related oligosaccharides, into biotin-tagged probes to analyze the precise carbohydrate specificity of two anti-HNK-1 antibodies by surface plasmon resonance that revealed a crucial role of the glucuronic acid in antibody binding. The contribution of the different oligosaccharide moieties in the interaction was shown by saturation transfer difference (STD) NMR of the complex consisting of the HNK-1 pentasaccharide and the HNK-1 412 antibody.

  DOI：

  10.1021/ja2083015