2'-N-(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)-aminoethyl α-D-mannopyranoside

• 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: 2'-N-(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)-aminoethyl α-D-mannopyranoside
• 英文别名: 4-ethoxy-2,3-dioxocyclobut-1-enyl-amino-ethyl-α-D-mannopyranoside；monovalent mannosyl squarate；3-ethoxy-4-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]cyclobut-3-ene-1,2-dione
• 化学式: C₁₄H₂₁NO₉
• 分子量: 347.322
• InChiKey: VZLFXQZZDPQIOZ-YXJHXQJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  三(2-氨基乙基)胺 、 2'-N-(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)-aminoethyl α-D-mannopyranoside 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以67.6%的产率得到tris-2-{N-[4-N-(α-D-mannopyranosyloxyethyl)-2,3-dioxocyclobut-1-enyl]aminoethyl}amine
  参考文献：
  名称：

  寡糖模拟物的功能化和使用方二酯介导的偶联的多聚化。

  摘要：

  功能化的以碳水化合物为中心的糖簇形成了用于合成标记的寡糖和糖缀合物模拟物的起始材料，其是通过硫脲桥接，肽偶联，尤其是方二酯介导的偶联而获得的。后一种方法也可用于提供新的多价糖缀合物，其在大肠埃希菌细菌的ELISA中经测试其抗黏附特性。

  DOI：

  10.1016/j.carres.2006.12.021
• 作为产物：
  描述：

  2-aminoethyl α-D-mannopyranoside 、 方酸二乙酯 以 甲醇 为溶剂， 反应 10.0h， 以71%的产率得到2'-N-(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)-aminoethyl α-D-mannopyranoside
  参考文献：
  名称：

  Evaluation of the carbohydrate recognition domain of the bacterial adhesin FimH: design, synthesis and binding properties of mannoside ligands

  摘要：

  菌毛是细菌表面的一种蛋白质衍生附属物，介导细菌与宿主细胞糖萼的粘附。所谓的一型菌毛对α-D-甘露糖苷具有特异性，因此假设它们通过菌毛凝集素与宿主细胞表面暴露的α-D-甘露糖基残基的相互作用来介导细菌粘附。这种一型菌毛的糖类特异性粘附蛋白亚单位已被鉴定为一种称为FimH的蛋白质。这种凝集素的晶体结构是已知的，基于这些信息，本文详细讨论了甘露糖苷配体与FimH相互作用的分子细节。使用基于计算机的对接方法来评估已知配体并设计新的配体。然后，合成了一系列具有扩展配基的新型甘露糖苷，并作为一型菌毛介导细菌粘附的抑制剂在ELISA中进行了测试。获得的实验结果与分子建模提供的预测和发现进行了比较。这项研究提高了对所研究配体-受体相互作用的理解。

  DOI：

  10.1039/b610745a

文献信息

• Evaluation of the carbohydrate recognition domain of the bacterial adhesin FimH: design, synthesis and binding properties of mannoside ligands
  作者：Oliver Sperling、Andreas Fuchs、Thisbe K. Lindhorst

  DOI：10.1039/b610745a

  日期：——

  Fimbriae are proteinogeneous appendages on the surface of bacteria, which mediate bacterial adhesion to the host cell glycocalyx. The so-called type 1 fimbriae exhibit specificity for α-D-mannosides and, therefore, they are assumed to mediate bacterial adhesion via the interaction of a fimbrial lectin and α-D-mannosyl residues exposed on the host cell surface. This carbohydrate-specific adhesive protein subunit of type 1 fimbriae has been identified as a protein called FimH. The crystal structure of this lectin is known and, based on this information, the molecular details of the interaction of mannoside ligands and FimH are addressed in this paper. Computer-based docking methods were used to evaluate known ligands as well as to design new ones. Then, a series of new mannosides with extended aglycon was synthesized and tested as inhibitors of type 1 fimbriae-mediated bacterial adhesion in an ELISA. The results obtained were compared to the predictions and findings as delivered by molecular modeling. This study led to an improved understanding of the ligand–receptor interactions under investigation.

  菌毛是细菌表面的一种蛋白质衍生附属物，介导细菌与宿主细胞糖萼的粘附。所谓的一型菌毛对α-D-甘露糖苷具有特异性，因此假设它们通过菌毛凝集素与宿主细胞表面暴露的α-D-甘露糖基残基的相互作用来介导细菌粘附。这种一型菌毛的糖类特异性粘附蛋白亚单位已被鉴定为一种称为FimH的蛋白质。这种凝集素的晶体结构是已知的，基于这些信息，本文详细讨论了甘露糖苷配体与FimH相互作用的分子细节。使用基于计算机的对接方法来评估已知配体并设计新的配体。然后，合成了一系列具有扩展配基的新型甘露糖苷，并作为一型菌毛介导细菌粘附的抑制剂在ELISA中进行了测试。获得的实验结果与分子建模提供的预测和发现进行了比较。这项研究提高了对所研究配体-受体相互作用的理解。
• Can Heterocyclic γ-Peptides Provide Polyfunctional Platforms for Synthetic Glycocluster Construction?
  作者：Matthieu Simon、Lamiaa M. A. Ali、Khaled El Cheikh、Julie Aguesseau、Magali Gary-Bobo、Marcel Garcia、Alain Morère、Ludovic T. Maillard

  DOI：10.1002/chem.201802032

  日期：2018.8.6

  interest of our group concerns the design of new highly predictable and stable molecular pseudo‐peptide architectures for therapeutic applications. In such a context, we described a class of constrained heterocyclic γ‐amino acids built around a thiazole ring, named ATCs. ATC oligomers are helical molecules resulting from the formation of a highly stable C9 hydrogen‐bonding pattern. Following our program

  糖在涉及一系列称为凝集素的蛋白质家族的许多分子和细胞通讯过程中起着关键作用。与糖识别相关的低亲和力通常被相互作用的多价性质所抵消。尽管已经描述了许多多糖基化的结构，但只有少数研究集中在多价结构的拓扑变化对与凝集素蛋白相互作用的影响上。我们小组的主要兴趣之一是设计用于治疗应用的新型高度可预测且稳定的分子假肽结构。在这种情况下，我们描述了围绕噻唑环构建的一类受约束的杂环γ-氨基酸，称为ATC。ATC低聚物是螺旋分子，由高度稳定的C 9形成氢键模式。按照我们的程序，我们在这里探讨了ATC低聚物作为开发原始多价糖簇的可调支架的潜力。
• Mannose‐BSA Conjugates: Comparison Between Commercially Available Linkers in Reactivity and Bioactivity
  作者：Masayuki Izumi、Shigeyoshi Okumura、Hideya Yuasa、Hironobu Hashimoto

  DOI：10.1081/car-120023475

  日期：2003.1.8

  Mannosyl ethanolamine and BSA were conjugated together by their amino groups with various homobifunctional cross-linker reagents: disuccinimidyl carbonate (DSC), disuccinimidyl glutarate (DSG), disuccinimidyl suberate (DSS), ethylene glycolbis-(succinimidylsuccinate) (EGS), 1,5-difluoro-2,4-dinitrobenzene (DFDNB), diethyl squarate (DES), and thiophosgene (TP). The resulting mannose-BSA conjugates were subjected to an enzyme-linked lectin assay (ELLA) to investigate their affinity to concanvalin A (ConA). With these results, the seven linkers were evaluated on the basis of five criteria, i.e., cost, reactivity, sugar loading, homogeneity, and affinity to ConA. Thus, DSS, DFDNB, and DES seemed to have advantages over the other cross-linking reagents.
• Synthesis and characterization of mannosylated oligoribonucleotides
  作者：Yuyan Zhao、Kha Tram、Hongbin Yan

  DOI：10.1016/j.carres.2009.08.033

  日期：2009.11

  Oligoribonucleotide (RNA)-carbohydrate conjugates bearing mono- and divalent mannosides were readily obtained using 3,4-diethoxy-3-cyclobutene-1,2-dione as the linking agent in the presence of trace amount of triethylamine. The glycoconjugates were purified by HPLC and characterized by electrospray mass spectroscopy.

  在痕量三乙胺的存在下，使用3,4-二乙氧基-3-环丁烯-1,2-二酮作为连接剂，可以轻松获得带有一价和二价甘露糖苷的寡核糖核苷酸（RNA）-碳水化合物共轭物。糖缀合物通过HPLC纯化，并通过电喷雾质谱法表征。
• Functionalization of oligosaccharide mimetics and multimerization using squaric diester-mediated coupling
  作者：Oliver Sperling、Michael Dubber、Thisbe K. Lindhorst

  DOI：10.1016/j.carres.2006.12.021

  日期：2007.4

  Functionalized carbohydrate-centered glycoclusters formed the starting material for the synthesis of tagged oligosaccharide and glycoconjugate mimetics, which were obtained by thiourea-bridging, peptide coupling and in particular squaric diester-mediated coupling. The latter method could also be utilized to provide new multivalent glycoconjugates, which were tested for their anti-adhesive properties

  功能化的以碳水化合物为中心的糖簇形成了用于合成标记的寡糖和糖缀合物模拟物的起始材料，其是通过硫脲桥接，肽偶联，尤其是方二酯介导的偶联而获得的。后一种方法也可用于提供新的多价糖缀合物，其在大肠埃希菌细菌的ELISA中经测试其抗黏附特性。