5-aminopentanyl α-D-glucopyranosyl-(1→2)-α-D-glucopyranoside | 1421768-05-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-aminopentanyl α-D-glucopyranosyl-(1→2)-α-D-glucopyranoside
• 英文别名: 5-aminopentanyl D-glucopyranosyl-(1→2)-α-D-glucopyranoside；5-aminopentyl α-D-glucopyranosyl-(1→2)-α-D-glucopyranoside；alpha-D-Glcp-(1->2)-alpha-D-GlcpO[CH2]5NH2；(2R,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-(5-aminopentoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1421768-05-9
• 化学式: C₁₇H₃₃NO₁₁
• 分子量: 427.449
• InChiKey: PAHYZUOWBCCBSP-SSNABBPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  205
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N-(benzyl)benzyloxycarbonyl-5-aminopentanyl 2,6-di-O-benzyl-3-O-(4-bromobenzyl)-α-D-glucopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.5h， 以99%的产率得到5-aminopentanyl α-D-glucopyranosyl-(1→2)-α-D-glucopyranoside
  参考文献：
  名称：

  [EN] OLIGOSACCHARIDES AND OLIGOSACCHARIDE-PROTEIN CONJUGATES DERIVED FROM CLOSTRIDIUM DIFFICILE POLYSACCARIDE PS-I, METHODS OF SYNTHESIS AND USES THEREOF, IN PARTICULAR AS VACCINES AND DIAGNOSTIC TOOLS
  [FR] OLIGOSACCHARIDES ET CONJUGUÉS D'OLIGOSACCHARIDES-PROTÉINES PROVENANT DE POLYSACCARIDES PS-I DE CLOSTRIDIUM DIFFICILE, LEURS PROCÉDÉS DE SYNTHÈSE ET D'UTILISATION, EN PARTICULIER EN TANT QUE VACCINS ET OUTILS DE DIAGNOSTIC

  摘要：

  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a-L-Rhap-（1→3）-β-D-Glcp-（1→4）-[a-L-Rhap-（1→3]-a-D-Glcp-（1→2）-a-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子L，用于与载体蛋白共轭或固定在表面上。该发明的进一步方面涉及有利的合成所述合成寡糖和寡糖-蛋白共轭的方法，以及它们的用途，特别是作为疫苗和诊断工具。

  公开号：

  WO2013017254A1

文献信息

• [EN] OLIGOSACCHARIDES AND OLIGOSACCHARIDE-PROTEIN CONJUGATES DERIVED FROM CLOSTRIDIUM DIFFICILE POLYSACCARIDE PS-I, METHODS OF SYNTHESIS AND USES THEREOF, IN PARTICULAR AS VACCINES AND DIAGNOSTIC TOOLS<br/>[FR] OLIGOSACCHARIDES ET CONJUGUÉS D'OLIGOSACCHARIDES-PROTÉINES PROVENANT DE POLYSACCARIDES PS-I DE CLOSTRIDIUM DIFFICILE, LEURS PROCÉDÉS DE SYNTHÈSE ET D'UTILISATION, EN PARTICULIER EN TANT QUE VACCINS ET OUTILS DE DIAGNOSTIC
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2013017254A1

  公开（公告）日：2013-02-07

  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 a-L-Rhap- ( 1→3 ) -β-D-Glcp- ( 1→4 ) - [a-L-Rhap- ( 1→3 ] -a-D-Glcp- ( 1→2 ) -a-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.

  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a-L-Rhap-（1→3）-β-D-Glcp-（1→4）-[a-L-Rhap-（1→3]-a-D-Glcp-（1→2）-a-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子L，用于与载体蛋白共轭或固定在表面上。该发明的进一步方面涉及有利的合成所述合成寡糖和寡糖-蛋白共轭的方法，以及它们的用途，特别是作为疫苗和诊断工具。
• Total synthesis of the<i>Helicobacter pylori</i>serotype O2 O-antigen α-(1 → 2)- and α-(1 → 3)-linked oligoglucosides
  作者：Guangzong Tian、Chunjun Qin、Zhonghua Liu、Dacheng Shen、Xiaopeng Zou、Junjie Fu、Jing Hu、Peter H. Seeberger、Jian Yin

  DOI：10.1039/c9cc07915g

  日期：——

  Exploiting synergistic remote participation effects of acyl groups at the O3 and O6 positions was key to the complete α-selectivity during the total synthesis of the unique (1 → 2)- and (1 → 3)-linked α-oligoglucosides from the Helicobacter pylori O2 O-antigen. Acyl remote participation and solvent effects were found to counteract during α-stereoselective glucosylations for the first time. The resulting

  在幽门螺杆菌中完全合成独特的（1→2）-和（1→3）-连接的α-寡糖苷的过程中，利用O3和O6位置的酰基的协同远程参与作用是完全α-选择性的关键。 O2 O抗原。首次发现在α-立体选择性葡萄糖基化过程中，酰基远程参与和溶剂作用相互抵消。所得抗原是开发碳水化合物缀合物疫苗的先导。
• Immunological Evaluation of a Synthetic Clostridium difficile Oligosaccharide Conjugate Vaccine Candidate and Identification of a Minimal Epitope
  作者：Christopher E. Martin、Felix Broecker、Matthias A. Oberli、Julia Komor、Jochen Mattner、Chakkumkal Anish、Peter H. Seeberger

  DOI：10.1021/ja401410y

  日期：2013.7.3

  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.