beta-D-Glcp-(1->3)-[beta-D-Glcp-(1->3)-beta-D-GalpNAc-(1->4)-alpha-D-Glcp-(1->4)]-beta-D-GalpNAc-(1->3)-alpha-D-ManpO[CH2]5NH2 | 1352618-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: beta-D-Glcp-(1->3)-[beta-D-Glcp-(1->3)-beta-D-GalpNAc-(1->4)-alpha-D-Glcp-(1->4)]-beta-D-GalpNAc-(1->3)-alpha-D-ManpO[CH2]5NH2
• 英文别名: N-[(2S,3R,4R,5R,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5R,6R)-2-(5-aminopentoxy)-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)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 1352618-38-2
• 化学式: C₄₅H₇₉N₃O₃₁
• 分子量: 1158.12
• InChiKey: RXCBAMIEGINJBX-NDEAUSGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11
• 重原子数：
  79
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  539
• 氢给体数：
  20
• 氢受体数：
  32

反应信息

• 作为反应物：
  描述：

  beta-D-Glcp-(1->3)-[beta-D-Glcp-(1->3)-beta-D-GalpNAc-(1->4)-alpha-D-Glcp-(1->4)]-beta-D-GalpNAc-(1->3)-alpha-D-ManpO[CH2]5NH2 、 方酸二乙酯 以 乙醇 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  A Possible Oligosaccharide-Conjugate Vaccine Candidate for Clostridium difficile Is Antigenic and Immunogenic

  摘要：

  Nosocomial infections with the Gram-positive pathogen Clostridium difficile pose a major risk for hospitalized patients and result in significant costs to health care systems. Here, we present the chemical synthesis of a PS-II hapten of a cell wall polysaccharide of hypervirulent ribotype 027 of C. difficile. Mice were immunized with a conjugate consisting of the synthetic hexasaccharide and the diphtheria toxoid variant CRM197. The immunogenicity of the glycan repeating unit was demonstrated by the presence of specific IgG antibodies in the serum of immunized mice. Murine monoclonal antibodies interact with the synthetic hexasaccharide, as determined by microarray analysis. Finally, we found that specific IgA antibodies in the stool of hospital patients infected with C. difficile recognize the synthetic PS-II hexasaccharide hapten.

  DOI：

  10.1016/j.chembiol.2011.03.009
• 作为产物：
  描述：

  在 甲醇 、 potassium hydroxide 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 beta-D-Glcp-(1->3)-[beta-D-Glcp-(1->3)-beta-D-GalpNAc-(1->4)-alpha-D-Glcp-(1->4)]-beta-D-GalpNAc-(1->3)-alpha-D-ManpO[CH2]5NH2
  参考文献：
  名称：

  A Possible Oligosaccharide-Conjugate Vaccine Candidate for Clostridium difficile Is Antigenic and Immunogenic

  摘要：

  Nosocomial infections with the Gram-positive pathogen Clostridium difficile pose a major risk for hospitalized patients and result in significant costs to health care systems. Here, we present the chemical synthesis of a PS-II hapten of a cell wall polysaccharide of hypervirulent ribotype 027 of C. difficile. Mice were immunized with a conjugate consisting of the synthetic hexasaccharide and the diphtheria toxoid variant CRM197. The immunogenicity of the glycan repeating unit was demonstrated by the presence of specific IgG antibodies in the serum of immunized mice. Murine monoclonal antibodies interact with the synthetic hexasaccharide, as determined by microarray analysis. Finally, we found that specific IgA antibodies in the stool of hospital patients infected with C. difficile recognize the synthetic PS-II hexasaccharide hapten.

  DOI：

  10.1016/j.chembiol.2011.03.009

文献信息

• A Possible Oligosaccharide-Conjugate Vaccine Candidate for Clostridium difficile Is Antigenic and Immunogenic
  作者：Matthias A. Oberli、Marie-Lyn Hecht、Pascal Bindschädler、Alexander Adibekian、Thomas Adam、Peter H. Seeberger

  DOI：10.1016/j.chembiol.2011.03.009

  日期：2011.5

  Nosocomial infections with the Gram-positive pathogen Clostridium difficile pose a major risk for hospitalized patients and result in significant costs to health care systems. Here, we present the chemical synthesis of a PS-II hapten of a cell wall polysaccharide of hypervirulent ribotype 027 of C. difficile. Mice were immunized with a conjugate consisting of the synthetic hexasaccharide and the diphtheria toxoid variant CRM197. The immunogenicity of the glycan repeating unit was demonstrated by the presence of specific IgG antibodies in the serum of immunized mice. Murine monoclonal antibodies interact with the synthetic hexasaccharide, as determined by microarray analysis. Finally, we found that specific IgA antibodies in the stool of hospital patients infected with C. difficile recognize the synthetic PS-II hexasaccharide hapten.