propyl α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside | 1091625-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Glc(a1-3)Rha(a1-2)Rha(a1-3)Rha(a1-3)GlcNAc(b)-O-Pr；N-[(2R,3R,4R,5S,6R)-4-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5R,6S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-propoxyoxan-3-yl]acetamide
• CAS: 1091625-90-9
• 化学式: C₃₅H₆₁NO₂₃
• 分子量: 863.862
• InChiKey: DMQMEGAQKBRFBT-OJKQKBNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  59
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  364
• 氢给体数：
  13
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  allyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→3)-(4-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 10% Pd on charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 以70%的产率得到propyl α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  从普通四糖中间体合成弗氏志贺菌血清型 3a 和 X O-抗原的两个四糖和四个五糖片段

  摘要：

  所得受体与 D 供体的糖基化，以及随后的部分或全部脱保护，得到支链五糖 D(E)ABAcC 和 D(E)ABC。所有目标都是志贺氏菌 3a 的 O 抗原的一部分，这是一种流行的血清型。非 O-乙酰化寡糖由 S.flexneri 血清型 X O-抗原共有。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800693

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。
• Efficient Iterative Synthesis of O-Acetylated Tri- to Pentadecasaccharides Related to the Lipopolysaccharide of<i>Shigella flexneri</i>Type 3 a through Di- and Trisaccharide Glycosyl Donors
  作者：Zhaoyu Hu、Aileen F. Bongat White、Laurence A. Mulard

  DOI：10.1002/asia.201600819

  日期：2017.2.16

  iteration with di‐ and trisaccharide building blocks provided fragments made of up to three mono‐O‐acetylated polysaccharide repeating units. Pd(OH)2‐mediated hydrogenation/hydrogenolysis enabled the concomitant removal or conversion of up to 31 protecting groups of 4 different origins to provide the targets as propyl glycosides. Oligosaccharides comprising the octasaccharide segment were shown to display

  可以通过针对细菌表面多糖的抗体来实现针对细菌感染（包括志贺菌病）的保护。为了开发针对志贺氏菌病的候选疫苗，我们在此报告了五糖，十糖和十五糖以及三糖，八糖和十三糖的合成，分别作为表面多糖的末端链和链内片段的弗氏志贺菌3，一个流行的血清型。合成过程依赖于三氯乙酰亚氨酸酯糖基化反应的效率，因此用二糖和三糖构建单元进行迭代可提供由最多三个单-O-乙酰化多糖重复单元组成的片段。钯（OH）2介导的氢化/氢解作用可同时除去或转化多达4个不同来源的31个保护基团，从而将目标物作为丙基糖苷提供。包含八糖链段的寡糖在溶液中显示出高构象相似性。
• Synthesis of Two Tetra- and Four Pentasaccharide Fragments of<i>Shigella flexneri</i>Serotypes 3a and X O-Antigens from a Common Tetrasaccharide Intermediate
  作者：Julien Boutet、Laurence A. Mulard

  DOI：10.1002/ejoc.200800693

  日期：2008.11

  Ac→2]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→}n ((E)ABAcCD)n polymer were synthesized as their propyl glycosides by use of a common fully protected (E)ABAcC intermediate (9). Tetrasaccharide 9 derived from the condensation of an EA donor and a BAcC acceptor. Partial and full deprotection gave free tetrasaccharides (E)ABAcC and (E)ABC, respectively. Alternatively, 9 was converted into a trichloroacetimidate

  所得受体与 D 供体的糖基化，以及随后的部分或全部脱保护，得到支链五糖 D(E)ABAcC 和 D(E)ABC。所有目标都是志贺氏菌 3a 的 O 抗原的一部分，这是一种流行的血清型。非 O-乙酰化寡糖由 S.flexneri 血清型 X O-抗原共有。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)