3-aminopropyl β-D-glucopyranosyl-(1→3)-[6-O-phospho-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→3)-α-D-mannopyranoside | 1262208-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-aminopropyl β-D-glucopyranosyl-(1→3)-[6-O-phospho-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→3)-α-D-mannopyranoside
• 英文别名: 3-aminopropyl β-D-glucopyranosyl-(1->3)-[6-O-phospho-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)]-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->3)-α-D-mannopyranoside；[(2R,3S,4S,5R,6R)-6-[(2S,3R,4R,5R,6R)-3-acetamido-2-[(2R,3S,4R,5R,6R)-6-[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5R,6R)-2-(3-aminopropoxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 1262208-71-8
• 化学式: C₄₃H₇₆N₃O₃₄P
• 分子量: 1210.05
• InChiKey: YLJNOMYDOPRRIG-FPZPFVPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -15.6
• 重原子数：
  81
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  585
• 氢给体数：
  21
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  3-aminopropyl β-D-glucopyranosyl-(1→3)-[6-O-phospho-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→3)-α-D-mannopyranoside 、 己二酸 1,6-二(2,5-二氧代-1-吡咯烷基)酯 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Phosphorylation of the Synthetic Hexasaccharide Repeating Unit Is Essential for the Induction of Antibodies to Clostridium difficile PSII Cell Wall Polysaccharide

  摘要：

  Clostridium difficile is emerging worldwide as a major cause of nosocomial infections. The negatively charged PSII polysaccharide has been found in different strains of C. difficile and, thereby, represents an important target molecule for a possible carbohydrate-based vaccine. In order to identify a synthetic fragment that after conjugation to a protein carrier could be able to induce anti-PSII antibodies, we exploited a combination of chemical synthesis with immunochemistry, confocal immunofluorescence microscopy, and solid state NMR. We demonstrate that the phosphate group is crucial in synthetic glycans to mimic the native PSII polysaccharide; both native PSII and a phosphorylated synthetic hexasaccharide repeating unit conjugated to CRM197 elicit comparable immunogenic responses in mice. This finding can aid design and selection of carbohydrate antigens to be explored as vaccine candidates

  DOI：

  10.1021/cb300221f
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以99%的产率得到3-aminopropyl β-D-glucopyranosyl-(1→3)-[6-O-phospho-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→3)-α-D-mannopyranoside
  参考文献：
  名称：

  COMPOUNDS

  摘要：

  该发明提供了一种合成的C. difficile PS-II细胞壁多糖。该发明还提供了一种从C. difficile细菌细胞中纯化C. difficile PS-II多糖的方法，从而减少污染。这些多糖可以用于疫苗，特别是作为与载体蛋白结合的共轭物。

  公开号：

  US20130315959A1

文献信息

• First Synthesis of <i>C. difficile</i> PS-II Cell Wall Polysaccharide Repeating Unit
  作者：Elisa Danieli、Luigi Lay、Daniela Proietti、Francesco Berti、Paolo Costantino、Roberto Adamo

  DOI：10.1021/ol1026188

  日期：2011.2.4

  difficile is the most commonly diagnosed cause of nosocomial diarrhea with increasing incidence and mortality among elderly and hospitalized patients. We report the first synthesis of the surface polysaccharide PS-II repeating unit and its nonphosphorylated analogue, with a linker for conjugation, via a (4 + 2) convergent approach from a common AB(D)C tetrasaccharide intermediate.

  艰难梭菌是医院内腹泻的最常见诊断原因，在老年人和住院患者中发病率和死亡率均在增加。我们报告了表面多糖PS-II重复单元及其非磷酸化类似物的首次合成，并通过（4 + 2）趋同方法从一个常见的AB（D）C四糖中间体进行缀合。
• COMPOUNDS
  申请人：Costantino Paolo

  公开号：US20130315959A1

  公开（公告）日：2013-11-28

  The invention provides a synthetic C. difficile PS-II cell wall saccharide. The invention also provides a process for purifying C. difficile PS-II saccharide from C. difficile bacterial cells resulting in reduced contamination. The saccharides may be used in vaccines, particularly as conjugates with carrier proteins.

  该发明提供了一种合成的C. difficile PS-II细胞壁多糖。该发明还提供了一种从C. difficile细菌细胞中纯化C. difficile PS-II多糖的方法，从而减少污染。这些多糖可以用于疫苗，特别是作为与载体蛋白结合的共轭物。
• Phosphorylation of the Synthetic Hexasaccharide Repeating Unit Is Essential for the Induction of Antibodies to <i>Clostridium difficile</i> PSII Cell Wall Polysaccharide
  作者：Roberto Adamo、Maria R. Romano、Francesco Berti、Rosanna Leuzzi、Marta Tontini、Elisa Danieli、Emilia Cappelletti、Osman S. Cakici、Erwin Swennen、Vittoria Pinto、Barbara Brogioni、Daniela Proietti、Cesira L. Galeotti、Luigi Lay、Mario A. Monteiro、Maria Scarselli、Paolo Costantino

  DOI：10.1021/cb300221f

  日期：2012.8.17

  Clostridium difficile is emerging worldwide as a major cause of nosocomial infections. The negatively charged PSII polysaccharide has been found in different strains of C. difficile and, thereby, represents an important target molecule for a possible carbohydrate-based vaccine. In order to identify a synthetic fragment that after conjugation to a protein carrier could be able to induce anti-PSII antibodies, we exploited a combination of chemical synthesis with immunochemistry, confocal immunofluorescence microscopy, and solid state NMR. We demonstrate that the phosphate group is crucial in synthetic glycans to mimic the native PSII polysaccharide; both native PSII and a phosphorylated synthetic hexasaccharide repeating unit conjugated to CRM197 elicit comparable immunogenic responses in mice. This finding can aid design and selection of carbohydrate antigens to be explored as vaccine candidates