p-[N-(2-ethoxy-3,4-dioxocyclobut-1-enyl)amino]phenyl α-D-mannopyranoside | 916849-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-[N-(2-ethoxy-3,4-dioxocyclobut-1-enyl)amino]phenyl α-D-mannopyranoside
• 英文别名: 3-ethoxy-4-[[4-(α-D-mannopyranosyloxy)phenyl]amino]-3-cyclobutene-1,2-dione；3-ethoxy-4-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanilino]cyclobut-3-ene-1,2-dione
• CAS: 916849-16-6
• 化学式: C₁₈H₂₁NO₉
• 分子量: 395.366
• InChiKey: CPHPCOAFZWCOON-GNELUTOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  p-[N-(2-ethoxy-3,4-dioxocyclobut-1-enyl)amino]phenyl α-D-mannopyranoside 、 L-苯基丙氨酸叔丁酯 反应 0.75h， 以100%的产率得到tert-butyl (3,4-dioxo-2-((4-(((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)amino)cyclobut-1-en-1-yl)-L-phenylalaninate
  参考文献：
  名称：

  方酸单酰胺甘露糖苷作为细菌凝集素FimH的配体：共价抑制还是没有？

  摘要：

  特定抗粘剂的候选人：方酸（SA）单酰胺具有非特异性地与胺交联的能力。已经显示，甘露聚糖SA单酰胺充当细菌凝集素FimH的特异性抑制剂，并且在凝集素的碳水化合物结合位点（CRD）内未发生共价生物缀合。

  DOI：

  10.1002/cbic.201000774
• 作为产物：
  描述：

  方酸二乙酯 、 4-氨基苯基-alpha-D-吡喃甘露糖苷 以 甲醇 为溶剂， 反应 24.0h， 以63%的产率得到p-[N-(2-ethoxy-3,4-dioxocyclobut-1-enyl)amino]phenyl 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

• Mannose-Functionalized Mesoporous Silica Nanoparticles for Efficient Two-Photon Photodynamic Therapy of Solid Tumors
  作者：Magali Gary-Bobo、Youssef Mir、Cédric Rouxel、David Brevet、Ilaria Basile、Marie Maynadier、Ophélie Vaillant、Olivier Mongin、Mireille Blanchard-Desce、Alain Morère、Marcel Garcia、Jean-Olivier Durand、Laurence Raehm

  DOI：10.1002/anie.201104765

  日期：2011.11.25

  Multifunctionalized mesoporous silica nanoparticles induce significant reduction of tumor size upon two‐photon excitation in the near‐infrared region while being nontoxic under daylight illumination. These nanoparticles were further tested for in vivo two‐photon photodynamic therapy (TPE‐PDT). A 70 % regression of tumor size after a single treatment was observed in athymic mice bearing tumor xenografts.

  Zap'em！多功能的介孔二氧化硅纳米粒子在近红外区域中受到两光子激发后，可显着减小肿瘤大小，而在日光照射下则无毒。这些纳米颗粒进一步进行了体内双光子光动力疗法（TPE-PDT）的测试。在携带肿瘤异种移植物的无胸腺小鼠中，单次治疗后观察到肿瘤大小降低了70％。
• Glycoarrays by a New Tandem Noncovalent-Covalent Modification of Polystyrene Microtiter Plates and their Interrogation with Live Cells
  作者：Carsten Grabosch、Katharina Kolbe、Thisbe K. Lindhorst

  DOI：10.1002/cbic.201200365

  日期：2012.9.3

  Glycoarrays—easier than ever: Glycoarrays were fabricated on polystyrene microtiter plates with great ease by using a tandem process that combined hydrophobic adsorption and thiourea bridging. They were validated by testing specific bacterial adhesion and its inhibition.

  糖阵列比以往任何时候都更容易：通过结合疏水吸附和硫脲桥联的串联工艺，可以在聚苯乙烯微量滴定板上轻松制造糖阵列。通过测试特定的细菌粘附及其抑制作用来验证它们。
• Squaric Acid Monoamide Mannosides as Ligands for the Bacterial Lectin FimH: Covalent Inhibition or Not?
  作者：Carsten Grabosch、Mirja Hartmann、Jörn Schmidt-Lassen、Thisbe K. Lindhorst

  DOI：10.1002/cbic.201000774

  日期：2011.5.2

  acid (SA) monoamides have the ability to crosslink unspecifically to amines. It has been shown that mannosidic SA monoamides serve as specific inhibitors of the bacterial lectin FimH and that no covalent bioconjugation within the lectin's carbohydrate binding site (CRD) occurs.

  特定抗粘剂的候选人：方酸（SA）单酰胺具有非特异性地与胺交联的能力。已经显示，甘露聚糖SA单酰胺充当细菌凝集素FimH的特异性抑制剂，并且在凝集素的碳水化合物结合位点（CRD）内未发生共价生物缀合。
• 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。