3-(benzyloxycarbonyl)aminopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 1236190-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(benzyloxycarbonyl)aminopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[3-(phenylmethoxycarbonylamino)propoxy]oxan-2-yl]methyl acetate
• CAS: 1236190-06-9
• 化学式: C₂₅H₃₃NO₁₂
• 分子量: 539.537
• InChiKey: IPXMVBZNTMISRM-DJCPXJLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonyl)aminopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 、 对甲苯磺酸 、 原乙酸三乙酯 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 C₂₆H₃₁NO₉
  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：

  3-(苄氧羰基氨基)-1-丙醇 、 2,3,4,6-四-O-乙酰基-α-D-吡喃甘露糖 三氯乙酰亚胺酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到3-(benzyloxycarbonyl)aminopropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  艰难梭菌PS-II细胞壁多糖重复单元的首次合成

  摘要：

  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。

  DOI：

  10.1021/ol1026188

文献信息

• 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。
• Polyene macrolide derivative
  申请人：Shionogi & Co., Ltd.

  公开号：US10246478B2

  公开（公告）日：2019-04-02

  The present invention is the following Amphotericin B derivative: wherein each symbol is defined in description. The compound of the present invention has 16th position (X) is urea structure, cyclic structure, hydroxyalkyl or substituted monoalkylcarbamoyl. The compound of the present invention has antifungal activity.

  本发明是以下两性霉素 B 衍生物： 其中各符号在说明中定义。本发明化合物的第 16 位（X）是脲结构、环状结构、羟烷基或取代的单烷基氨基甲酰基。本发明化合物具有抗真菌活性。
• POLYENE MACROLIDE DERIVATIVE
  申请人：Shionogi & Co., Ltd.

  公开号：US20190135847A1

  公开（公告）日：2019-05-09

  The present invention is the following Amphotericin B derivative: wherein each symbol is defined in description. The compound of the present invention has 16th position (X) is urea structure, cyclic structure, hydroxyalkyl or substituted monoalkylcarbamoyl. The compound of the present invention has antifungal activity.
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：NOVARTIS AG

  公开号：WO2012085668A2

  公开（公告）日：2012-06-28

  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.