allyl 2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranoside | 1061181-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranoside
• 英文别名: N-[(4aR,6R,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2,2,2-trichloroacetamide
• CAS: 1061181-52-9
• 化学式: C₁₄H₂₀Cl₃NO₆
• 分子量: 404.675
• InChiKey: OSZXKDKGRKHJPR-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 allyl (α-L-rhamnopyranosyl)-(1→3)-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside
  参考文献：
  名称：

  Programmed chemo-enzymatic synthesis of the oligosaccharide component of a carbohydrate-based antibacterial vaccine candidate

  摘要：

  报道了一种强大的化学酶合成方法，用于合成第一个基于合成糖基疫苗候选物的十五糖肽半抗原，以对抗地方性志贺菌痢疾。

  DOI：

  10.1039/c4cc08805k
• 作为产物：
  描述：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 在 吡啶 、 甲醇 、 camphor-10-sulfonic acid 、 sodium methylate 、 TMSOTf 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 allyl 2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] PROTECTED TETRASACCHARIDES, THEIR PROCESS OF PREPARATION AND THEIR USE AS TRANSGLUCOSYLASE ACCEPTOR SUBSTRATES IN THE CHEMO-ENZYMATIC SYNTHESIS OF SHIGELLA FLEXNERI SPECIFIC OLIGOSACCHARIDES
  [FR] TÉTRAHOLOSIDES PROTÉGÉS, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION EN TANT QUE SUBSTRATS ACCEPTEURS DE TRANSGLUCOSYLASE DANS LA SYNTHÈSE CHIMIO-ENZYMATIQUE D'OLIGOSACCHARIDES SHIGELLA FLEXNERI SPÉCIFIQUES

  摘要：

  本发明提供了受保护的四糖，它们的制备方法以及它们在合成寡糖中的应用，特别是从菌群弯曲杆菌（Shigella flexneri）中的O-抗原片段，例如la、lb、2a、2b、3a、X、4a、4b、5a、5b、7a或7b的片段。

  公开号：

  WO2019007999A1

文献信息

• Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X
  申请人：Mulard Laurence

  公开号：US08815239B2

  公开（公告）日：2014-08-26

  The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present invention relates to novel glycoconjugated compounds comprising oligosaccharides or polysaccharides described hereinafter, to the method for synthesizing these oligosaccharides or polysaccharides and glycoconjugates, to derivatives of these oligosaccharides or polysaccharides, to compositions containing same, and also to the use of the glycoconjugates for vaccination purposes. Finally, the present invention relates to methods for diagnosing a Shigella flexneri infection using one or more oligosaccharides or polysaccharides or conjugates thereof.

  本发明涉及从糖类衍生的化合物，其重现志贺氏菌弗氏菌血清型3a和X的表位，并且涉及将其用于制备疫苗组合物。更具体地，本发明涉及包括下文描述的寡糖或多糖的新型糖结合化合物，用于合成这些寡糖或多糖和糖结合物的方法，这些寡糖或多糖的衍生物，含有这些衍生物的组合物，以及将糖结合物用于疫苗目的的用途。最后，本发明涉及使用一个或多个寡糖或多糖或其结合物诊断志贺氏菌弗氏菌感染的方法。
• GLYCOCONJUGATES AND USE THEREOF AS VACCINE AGAINST SHIGELLA FLEXNERI SEROTYPE 3A AND X
  申请人：Mulard Laurence

  公开号：US20100239584A1

  公开（公告）日：2010-09-23

  The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present invention relates to novel glycoconjugated compounds comprising oligosaccharides or polysaccharides described hereinafter, to the method for synthesizing these oligosaccharides or polysaccharides and glycoconjugates, to derivatives of these oligosaccharides or polysaccharides, to compositions containing same, and also to the use of the glycoconjugates for vaccination purposes. Finally, the present invention relates to methods for diagnosing a Shigella flexneri infection using one or more oligosaccharides or polysaccharides or conjugates thereof.

  本发明涉及从糖类衍生的化合物，这些化合物重现Shigella flexneri血清型3a和X的表位，并且用于制备疫苗组合物。更具体地，本发明涉及包含下文描述的寡糖或多糖的新型糖结合化合物，用于合成这些寡糖或多糖和糖结合物的方法，这些寡糖或多糖的衍生物，含有这些化合物的组合物，以及将糖结合物用于疫苗目的的用途。最后，本发明涉及使用一个或多个寡糖或多糖或其共轭物诊断Shigella flexneri感染的方法。
• Detailed Investigation of the Immunodominant Role of O-Antigen Stoichiometric O-Acetylation as Revealed by Chemical Synthesis, Immunochemistry, Solution Conformation and STD-NMR Spectroscopy for<i>Shigella flexneri</i> 3a
  作者：Julien Boutet、Pilar Blasco、Catherine Guerreiro、Françoise Thouron、Sylvie Dartevelle、Farida Nato、F. Javier Cañada、Ana Ardá、Armelle Phalipon、Jesús Jiménez-Barbero、Laurence A. Mulard

  DOI：10.1002/chem.201600567

  日期：2016.7.25

  bacillary dysentery. Its O‐antigen has the 2)‐[α‐d‐Glcp‐(1→3)]‐α‐l‐Rhap‐(1→2)‐α‐l‐Rhap‐(1→3)‐[Ac→2]‐α‐l‐Rhap‐(1→3)‐[Ac→6]≈40 %‐β‐d‐GlcpNAc‐(1→} ([(E)ABAcCAcD]) repeating unit, and the non‐O‐acetylated equivalent defines S. flexneri X. Propyl hepta‐, octa‐, and decasaccharides sharing the (E′)A′BAcCD(E)A sequence, and their non‐O‐acetylated analogues were synthesized from a fully protected BAcCD(E)A allyl

  弗氏志贺氏菌 3a引起细菌性痢疾。其O-抗原具有2） - [α- d -Glc p - （1→3）] - α-升-RHA p - （1→2）-α-升-RHA p - （1→3） ‐ [Ac→2] ‐α ‐ l ‐Rha p ‐（1→3）‐ [Ac→6] ≈40％ ‐β‐ d ‐Glc p NAc‐（1→}（[[E）AB Ac C Ac d]）的重复单元，并且所述非ö -acetylated等效限定弗氏志贺菌 X.丙基七- ，八，十糖和共享（E'）A'B AC CD（E）序列，和它们的非Ø从完全保护的B Ac CD（E）A烯丙基糖苷合成‐乙酰化的类似物。逐步引入正交保护的单糖和二糖亚氨酸酯供体，然后进行两步脱保护过程。通过抑制酶联免疫吸附测定（ELISA）和STD-NMR光谱研究了与二十六个弗氏链球菌3a型和X二糖结合至十糖的单克隆抗体。表位作图显示，2 C-乙酸盐主导了单克隆IgG和IgM抗体的识别，而B
• GLYCOCONJUGATES AND USE THEREOF AS VACCINE AGAINST SHIGELLA FLEXNERI SEROTYPE 3a AND X
  申请人：INSTITUT PASTEUR

  公开号：US20150050282A1

  公开（公告）日：2015-02-19

  The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present invention relates to novel glycoconjugated compounds comprising oligosaccharides or polysaccharides described hereinafter, to the method for synthesizing these oligosaccharides or polysaccharides and glycoconjugates, to derivatives of these oligosaccharides or polysaccharides, to compositions containing same, and also to the use of the glycoconjugates for vaccination purposes. Finally, the present invention relates to methods for diagnosing a Shigella flexneri infection using one or more oligosaccharides or polysaccharides or conjugates thereof.

  本发明涉及从糖衍生物中复制Shigella flexneri 3a和X血清型表位的化合物，以及用于制备疫苗组分的使用方法。更具体地说，本发明的主题涉及新型糖连接化合物，包括下文描述的寡糖或多糖，以及合成这些寡糖或多糖和糖连接物的方法，这些寡糖或多糖的衍生物，含有它们的组合物，以及将糖连接物用于疫苗接种目的的用途。最后，本发明涉及使用一种或多种寡糖或多糖或其共轭物来诊断Shigella flexneri感染的方法。
• Efficient route to orthogonally protected precursors of 2-acylamino-2-deoxy-3-O-substituted-β-d-glucopyranose derivatives and use thereof
  作者：Julien Boutet、Tae Hee Kim、Catherine Guerreiro、Laurence A. Mulard

  DOI：10.1016/j.tetlet.2008.06.052

  日期：2008.9

  An efficient route to two 3-O-acyl-2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-D-glucopyranosyl trichloroacetimidate donors is reported. As demonstrated for the 3-O-acetyl derivative, these building blocks are exquisite beta-D-glucosamine donors when reacted either with simple alcohols or with complex oligosaccharides. Besides, their protection pattern is compatible with selective deprotection and subsequent chain elongation at O-3 of the newly incorporated glucosamine residue. (C) 2008 Elsevier Ltd. All rights reserved.