2-aminoethyl α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→3)-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→2)-(3-O-acetyl-α-L-rhamnopyranosyl)-(1→2)-α-L-rhamnopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside | 1349064-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→3)-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→2)-(3-O-acetyl-α-L-rhamnopyranosyl)-(1→2)-α-L-rhamnopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-aminoethyl alpha-L-rhamnosyl-(1->2)-alpha-L-rhamnosyl-(1->3)-[alpha-D-glucosyl-(1->4)]-alpha-L-rhamnosyl-(1->3)-6-O,N-diacetyl-beta-D-glucosaminyl-(1->2)-3-O-acetyl-alpha-L-rhamnosyl-(1->2)-alpha-L-rhamnosyl-(1->3)-[alpha-D-glucosyl-(1->4)]-alpha-L-rhamnosyl-(1->3)-N-acetyl-beta-D-glucosaminide；[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-(2-aminoethoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-hydroxy-6-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl]oxy-4-acetyloxy-5-hydroxy-6-methyloxan-3-yl]oxy-4-[(2S,3R,4S,5S,6S)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-6-methyl-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxyoxan-2-yl]methyl acetate
• CAS: 1349064-45-4
• 化学式: C₇₀H₁₁₇N₃O₄₇
• 分子量: 1752.69
• InChiKey: HNOCXQTWTVVYEK-SQZBZXTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.7
• 重原子数：
  120
• 可旋转键数：
  31
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  746
• 氢给体数：
  24
• 氢受体数：
  48

反应信息

• 作为产物：
  描述：

  2-azidoethyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→4)]-(α-L-rhamnopyranosyl)-(1→3)-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→2)-(3-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-Lrhamnopyranosyl)-(1→3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→4)]-(α-L-rhamnopyranosyl)-(1→3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 盐酸 、 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 以48%的产率得到2-aminoethyl α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→3)-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→2)-(3-O-acetyl-α-L-rhamnopyranosyl)-(1→2)-α-L-rhamnopyranosyl-(1→3)-[α-D-glucopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  弗氏志贺氏菌2a O特异性多糖的非化学计量O-乙酰化：合成和抗原性†

  摘要：

  来自弗氏志贺氏菌2a的O抗原的合成功能模拟物被认为是对抗地方性志贺氏菌病的有前途的疫苗成分。在此，首次解决了多糖非化学计量的二-O-乙酰化对抗原性的影响。从十个关键的保护性十糖合成了三个十糖，它们代表了O抗原的相关内部单-和二-O-乙酰化分布，其目的是定制后期的位点选择性O-乙酰化。后者通过涉及亚氨酸酯糖基化化学的收敛途径获得。对五种保护性mIgG的结合研究表明，没有一种乙酸盐能显着增加广泛的抗体识别能力。然而，五种抗体之一具有独特的结合模式。带IC50在微摩尔至亚微摩尔范围mIgG F22-4例示了显着的紧密结合抗体针对的医学重要性的中性多糖的多样化O-乙酰化和非O-乙酰化的片段。

  DOI：

  10.1039/c3ob42586j