S-(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-1-thio-ß-D-glucopyranoside | 1334540-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-1-thio-ß-D-glucopyranoside
• 英文别名: (2-methyl-5-tert-butylphenyl)4,6-O-benzylidene-2-O-benzyl-1-thio-β-D-glucopyranoside
• CAS: 1334540-41-8
• 化学式: C₃₁H₃₆O₅S
• 分子量: 520.69
• InChiKey: OISZLUOUFARGED-QAZKHYNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  S-(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-1-thio-ß-D-glucopyranoside 在 三氟甲磺酸 、 TES 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 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：

  (2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-ß-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以1.77 g的产率得到S-(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-1-thio-ß-D-glucopyranoside
  参考文献：
  名称：

  Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: synthesis of the cell-surface polysaccharide PS-I repeating unit

  摘要：

  克劳斯特里迪姆·迪菲西尔株核糖型027是一种高度毒力病原体，导致了最近严重的医院感染暴发。作为开发基于碳水化合物的预防性疫苗的基础，我们通过对四种单糖构件进行线性组合，合成了该株特有的PS-I五糖细胞壁重复单元。

  DOI：

  10.1039/c1cc13614c

文献信息

• Oligosaccharides and oligosaccharides-protein conjugates derived from clostridium difficile polysaccharide PS-I, methods of synthesis and uses thereof, in particular as vaccines and diagnostic tools
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2554549A1

  公开（公告）日：2013-02-06

  The invention relates to a synthetic oligosaccharide representing part of the repeating unit of the Clostridium difficile glycopolymer PS-I and having the sequence of the pentasaccharide α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→2)-α-D-Glcp or a synthetic fragment or derivative thereof. Preferably, the claimed synthetic oligosaccharide bears at least one linker L for conjugation to a carrier protein or for immobilization on a surface. Further aspects of the invention relate to advantageous methods for synthesizing said synthetic oligosaccharide and oligosaccharide-protein conjugate as well as to uses thereof, in particular as vaccines and diagnostic tools. A preferred method for synthesizing the pentasaccharide is shown below.

  该发明涉及一种合成的寡糖，代表Clostridium difficile糖聚合物PS-I的重复单元的一部分，并具有五糖基序列α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→2)-α-D-Glcp或其合成片段或衍生物。优选，所述的合成寡糖至少带有一个连接体L，用于与载体蛋白结合或在表面上固定。该发明的其他方面涉及有利的合成所述合成寡糖和寡糖-蛋白共轭物的方法，以及它们的用途，特别是作为疫苗和诊断工具。下面显示了一种合成五糖基的首选方法。
• [EN] VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE SEROTYPE 8<br/>[FR] VACCINS CONTRE STREPTOCOCCUS PNEUMONIAE SÉROTYPE 8
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2016046420A1

  公开（公告）日：2016-03-31

  The present invention relates to synthetic saccharides of general formula (I) that are related to Streptococcuspneumoniae serotype 8 capsular polysaccharide, conjugates thereof and the use of said saccharides and conjugates for raising a protective immune response in a human and/or animal host. Furthermore, the synthetic saccharide structures of general formula (I) are useful as marker in immunological assays for detection of antibodies against Streptococcuspneumoniae bacteria.

  本发明涉及一般式（I）的合成糖苷，与肺炎链球菌8型蒽聚糖有关，以及它们的结合物，以及利用所述糖苷和结合物在人类和/或动物宿主中引发保护性免疫反应。此外，一般式（I）的合成糖苷结构可用作免疫学检测中的标记，用于检测针对肺炎链球菌细菌的抗体。