[(2R,3S,4S,5R,6R)-6-azido-4,5-dibenzoyloxy-3-hydroxyoxan-2-yl]methyl benzoate | 73108-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3S,4S,5R,6R)-6-azido-4,5-dibenzoyloxy-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 73108-20-0
• 化学式: C₂₇H₂₃N₃O₈
• 分子量: 517.495
• InChiKey: CEQABGFDWRGSQU-OYTPZHDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6R)-6-azido-4,5-dibenzoyloxy-3-hydroxyoxan-2-yl]methyl benzoate 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  使用刚性间隔垫优化铜绿假单胞菌凝集素LecA的二价抑制剂

  摘要：

  刚性间隔物：已经制备了铜绿假单胞菌凝集素LecA的最佳高效二价配体。配体由衍生自葡萄糖-三唑单元的刚性间隔基组成（见图）。间隔基单元和糖苷配基接头数量的系统变化导致效价提高了7500倍。

  DOI：

  10.1002/chem.201303463
• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷 在 吡啶 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 [(2R,3S,4S,5R,6R)-6-azido-4,5-dibenzoyloxy-3-hydroxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  A galabiose-based two-dimensional scaffold for the synthesis of inhibitors targeting Pk- and P-antigen binding proteins

  摘要：

  A disaccharide scaffold based on galabiose (Galal-4Gal) was synthesized. Four different acceptors were evaluated in the alpha-galactosylation and a relationship between the nucleophilicity, yield, and alpha/beta-selectivity was found. The scaffold contains two orthogonal derivatisation sites, i.e. at O-2' and the anomeric position, and as proof of concept, one derivatised galabioside was synthesized. Compounds based on this galabiose-scaffold are potential inhibitors of P- and P-k-antigen binding proteins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00475-1

文献信息

• Fighting <i>Shigella</i> by Blocking Its Disease-Causing Toxin
  作者：Diksha Haksar、Mostafa Asadpoor、Torben Heise、Jie Shi、Saskia Braber、Gert Folkerts、Lluis Ballell、Janneth Rodrigues、Roland J. Pieters

  DOI：10.1021/acs.jmedchem.1c00152

  日期：2021.5.13

  Shiga toxin is an AB5 toxin produced by Shigella species, while related toxins are produced by Shiga toxin-producing Escherichia coli (STEC). Infection by Shigella can lead to bloody diarrhea followed by the often fatal hemolytic uremic syndrome (HUS). In the present paper, we aimed for a simple and effective toxin inhibitor by comparing three classes of carbohydrate-based inhibitors: glycodendrimers

  志贺毒素是志贺氏菌物种产生的AB 5毒素，而相关毒素则是由产生志贺毒素的大肠杆菌产生的（STEC）。志贺氏菌感染可导致血性腹泻，然后导致致命的溶血性​​尿毒症综合征（HUS）。在本文中，我们通过比较三类基于碳水化合物的抑制剂（糖类树状聚合物，糖聚合物和寡糖）来寻找一种简单有效的毒素抑制剂。我们观察到多价抑制剂的效力明显增强，其中二价和四价化合物分别抑制在毫摩尔和微摩尔范围内。但是，基于galabiose的聚合物抑制剂在显示纳摩尔抑制作用的系列中是最有效的。海藻酸盐和壳聚糖低聚糖也抑制志贺氏菌毒素，可在志贺氏菌爆发期间用作预防药物。
• Assembly of Divalent Ligands and Their Effect on Divalent Binding to <i>Pseudomonas aeruginosa</i> Lectin LecA
  作者：Guangyun Yu、Anna Chiara Vicini、Roland J. Pieters

  DOI：10.1021/acs.joc.8b02727

  日期：2019.3.1

  to optimize dynamics and enhance interactions with the protein. Affinities of the divalent ligands were measured by ITC, and Kd's as low as 12 nM were determined, notably for a compounds with either a rigid (phenyl) or flexible (butyl) unit at the core. Introducing a phenyl aglycon moiety next to the galactoside ligands on both termini did indeed lead to a higher enthalpy of binding, which was more than

  制备二价配体作为有问题的铜绿假单胞菌病原体粘附蛋白的抑制剂。桥接两个结合位点使得能够同时结合两个半乳糖部分，这大大增强了结合。葡萄糖，三唑和芳基的交替基序显示具有刚性，溶解性和易于合成的正确组合。间隔物相对于核心单元以及糖苷配基部分是变化的，以试图优化动力学并增强与蛋白质的相互作用。通过ITC测量二价配体的亲和力，并确定低至12 nM的Kd，特别是对于在核心具有刚性（苯基）或柔性（丁基）单元的化合物。在两个末端的半乳糖苷配体旁边引入苯基糖苷配基部分的确确实导致了更高的结合焓，这被熵成本所补偿。将根据热力学以及对预期和观察到的多价效应的理论计算来讨论结果。
• Optimizing Divalent Inhibitors of<i>Pseudomonas aeruginosa</i>Lectin LecA by Using A Rigid Spacer
  作者：Francesca Pertici、Nico J. de Mol、Johan Kemmink、Roland J. Pieters

  DOI：10.1002/chem.201303463

  日期：2013.12.9

  Rigid spacers: Optimal highly potent divalent ligands of the P. aeruginosa lectin LecA have been prepared. The ligands consist of a rigid spacer derived from glucose–triazole units (see figure). Systematic variation of the number of spacer units and the aglycon linker led to a 7500‐fold enhancement in potency.

  刚性间隔物：已经制备了铜绿假单胞菌凝集素LecA的最佳高效二价配体。配体由衍生自葡萄糖-三唑单元的刚性间隔基组成（见图）。间隔基单元和糖苷配基接头数量的系统变化导致效价提高了7500倍。
• A galabiose-based two-dimensional scaffold for the synthesis of inhibitors targeting Pk- and P-antigen binding proteins
  作者：Jörgen Ohlsson、Ulf J. Nilsson

  DOI：10.1016/s0040-4039(03)00475-1

  日期：2003.3

  A disaccharide scaffold based on galabiose (Galal-4Gal) was synthesized. Four different acceptors were evaluated in the alpha-galactosylation and a relationship between the nucleophilicity, yield, and alpha/beta-selectivity was found. The scaffold contains two orthogonal derivatisation sites, i.e. at O-2' and the anomeric position, and as proof of concept, one derivatised galabioside was synthesized. Compounds based on this galabiose-scaffold are potential inhibitors of P- and P-k-antigen binding proteins. (C) 2003 Elsevier Science Ltd. All rights reserved.