(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-3-O-(4-bromo)benzyl-1-thio-β-D-glucopyranoside | 1421767-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-3-O-(4-bromo)benzyl-1-thio-β-D-glucopyranoside
• CAS: 1421767-95-4
• 化学式: C₃₈H₄₁BrO₅S
• 分子量: 689.711
• InChiKey: NOUJPJGROJSHGC-KUDKMFMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.16
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-3-O-(4-bromo)benzyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸 、 TES 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2-methyl-5-tert-butylphenyl) 2,6-di-O-benzyl-3-O-(4-bromo)benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Immunological Evaluation of a Synthetic Clostridium difficile Oligosaccharide Conjugate Vaccine Candidate and Identification of a Minimal Epitope

  摘要：

  Clostridium difficile is the cause of emerging nosocomial infections that result in abundant morbidity and mortality worldwide. Thus, the development of a vaccine to kill the bacteria to prevent this disease is highly desirable. Several recently identified bacterial surface glycans, such as PS-I and PS-II, are promising vaccine candidates to preclude C difficile infection. To circumvent difficulties with the generation of natural PS-I due to its low expression levels in bacterial cultures, improved chemical synthesis protocols for the pentasaccharide repeating unit of PS-I and oligosactharide substructures were utilized to produce large quantities of well-defined PS-I related glycans. The analysis of stool and serum samples obtained from C. difficile patients using glycan microarrays of synthetic oligosaccharide epitopes revealed humoral immune responses to the PS-I related glycan epitopes. Two different vaccine candidates were evaluated in the mouse model. A synthetic PS-I repeating unit CRM197 conjugate was immunogenic in mice and induced immunoglobulin class switching as well as affinity maturation. Microarray screening employing PS-I repeating unit substructures revealed the disaccharide Rha-(1 -> 3)-Glc as a minimal epitope. A CRM197-Rha-(1 -> 3)-Glc disaccharide conjugate was able to elicit antibodies recognizing the C. difficile PS-I pentasaccharide. We herein demonstrate that glycan microarrays exposing defined oligosaccharide epitopes help to determine the minimal immunogenic epitopes of complex oligosaccharide antigens. The synthetic PS-I pentasaccharide repeating unit as well as the Rha-(1 -> 3)-Glc disaccharide are promising novel vaccine candidates against C difficile that are currently in preclinical evaluation.

  DOI：

  10.1021/ja401410y
• 作为产物：
  描述：

  S-(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-1-thio-ß-D-glucopyranoside 、 对溴溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以1.55 g的产率得到(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-3-O-(4-bromo)benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Immunological Evaluation of a Synthetic Clostridium difficile Oligosaccharide Conjugate Vaccine Candidate and Identification of a Minimal Epitope

  摘要：

  Clostridium difficile is the cause of emerging nosocomial infections that result in abundant morbidity and mortality worldwide. Thus, the development of a vaccine to kill the bacteria to prevent this disease is highly desirable. Several recently identified bacterial surface glycans, such as PS-I and PS-II, are promising vaccine candidates to preclude C difficile infection. To circumvent difficulties with the generation of natural PS-I due to its low expression levels in bacterial cultures, improved chemical synthesis protocols for the pentasaccharide repeating unit of PS-I and oligosactharide substructures were utilized to produce large quantities of well-defined PS-I related glycans. The analysis of stool and serum samples obtained from C. difficile patients using glycan microarrays of synthetic oligosaccharide epitopes revealed humoral immune responses to the PS-I related glycan epitopes. Two different vaccine candidates were evaluated in the mouse model. A synthetic PS-I repeating unit CRM197 conjugate was immunogenic in mice and induced immunoglobulin class switching as well as affinity maturation. Microarray screening employing PS-I repeating unit substructures revealed the disaccharide Rha-(1 -> 3)-Glc as a minimal epitope. A CRM197-Rha-(1 -> 3)-Glc disaccharide conjugate was able to elicit antibodies recognizing the C. difficile PS-I pentasaccharide. We herein demonstrate that glycan microarrays exposing defined oligosaccharide epitopes help to determine the minimal immunogenic epitopes of complex oligosaccharide antigens. The synthetic PS-I pentasaccharide repeating unit as well as the Rha-(1 -> 3)-Glc disaccharide are promising novel vaccine candidates against C difficile that are currently in preclinical evaluation.

  DOI：

  10.1021/ja401410y