2-氯-4-硝基苯基-a-D-吡喃甘露糖苷 | 65446-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-4-硝基苯基-a-D-吡喃甘露糖苷
• 英文名称: 2-chloro-4-nitrophenyl α-D-mannopyranoside
• 英文别名: 2-chloro-4-nitrophenyl-α-D-mannopyranoside；o-Chlor-p-nitrophenyl α-D-mannopyranose；(2R,3S,4S,5S,6R)-2-(2-Chloro-4-nitrophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2R,3S,4S,5S,6R)-2-(2-chloro-4-nitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 65446-24-4
• 化学式: C₁₂H₁₄ClNO₈
• 分子量: 335.698
• InChiKey: PJCVBKZRKNFZOD-GCHJQGSQSA-N

物化性质

• 沸点：
  591.2±50.0 °C(Predicted)
• 密度：
  1.675±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-氯-4-硝基苯基-a-D-吡喃甘露糖苷 在 N,N′-{1,3-bis[(pyridine-2-ylmethyl)amino]propan-2-al}atodicopper(II)(μ-acetato)diperchlorate 、 水 、 4-羟乙基哌嗪乙磺酸 作用下， 以 aq. buffer 为溶剂， 生成 D-甘露糖
  参考文献：
  名称：

  CHIRAL BINUCLEAR METAL COMPLEXES FOR STEREOSELECTIVE GLYCOSIDE HYDROLYSIS OF SACCHARIDES

  摘要：

  本文揭示了一类手性双核金属配合物，用于在接近生理pH值的水溶液中对糖类进行立体选择性水解，更具体地说，是手性双核过渡金属配合物催化剂，可以区分糖类的对映异构体和α-和β-糖苷键。这些手性双核金属配合物包括来源于手性二胺建筑块的席夫碱型配体和双核过渡金属核心，每个都可以根据选择性进行变化。金属核心是一种路易斯酸性金属离子，例如铜、锌、镧、铁和镍。席夫碱可以是从脂肪线性、脂肪环状二胺醇或芳香醛衍生的还原或非还原的席夫碱。配体可以是从吡啶甲醛、苯甲醛、线性或环状二胺或二胺醇衍生的五齿或七齿配体。

  公开号：

  US20170275303A1
• 作为产物：
  描述：

  2-chloro-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 以71%的产率得到2-氯-4-硝基苯基-a-D-吡喃甘露糖苷
  参考文献：
  名称：

  区分水溶液中差向异构糖苷和α-和β-糖苷键的双核铜（II）配合物

  摘要：

  合成了两种手性双核铜（II）配合物，并首次将其表征为在接近中性pH的水溶液中水解芳基糖苷和二糖的有效化学选择性催化剂。在这些条件下，通过29倍不同的反应速率和3倍不同的催化剂熟练度观察到了差向异构体芳基α-吡喃葡萄糖苷。此外，α-和β的性质有很大的区别作为模型化合物的芳基糖苷中的β-糖苷键是显而易见的，但在选定的二糖中也注意到。详细讨论了配合物的手性和碳水化合物构型的作用对与催化剂相互作用的影响。最后，金属配合物催化水解的推定机理是从实验证据中得出的，该实验证据表明C-2处羟基的去质子化是糖苷水解的先决条件。

  DOI：

  10.1016/j.jcat.2015.12.026

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。
• GLYCOSYLTRANSFERASE REVERSIBILITY FOR SUGAR NUCLEOTIDE SYNTHESIS AND MICROSCALE SCANNING
  申请人：Thorson Jon S.

  公开号：US20130004979A1

  公开（公告）日：2013-01-03

  The present invention generally relates to materials and methods for exploiting glycosyltransferase reversibility for nucleotide diphosphate (NDP) sugar synthesis. The present invention provides engineered glycosyltransferase enzymes characterized by improved reaction reversibility and expanded sugar donor specificity as compared to corresponding non-mutated glycosyltransferase enzymes. Such reagents provide advantageous routes to NDP sugars for subsequent use in a variety of biomedical applications, including enzymatic and chemo-enzymatic glycorandomization.

  本发明一般涉及利用糖基转移酶可逆性合成核苷酸二磷酸（NDP）糖的材料和方法。本发明提供了改良反应可逆性并扩展糖供体特异性的工程糖基转移酶酶，与相应的非突变糖基转移酶酶相比，具有更好的反应可逆性和扩展的糖供体特异性。这些试剂提供了有利的NDP糖路线，用于随后在各种生物医学应用中使用，包括酶促和化学酶促糖随机化。
• Chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides
  申请人：BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS

  公开号：US10870103B2

  公开（公告）日：2020-12-22

  Disclosed herein is a class of chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides, and more particular chiral binuclear transition metal complex catalysts that discriminate epimeric glycosides and α- and β-glycosidic bonds of saccharides in aqueous solutions at near physiological pHs. The chiral binuclear metal complexes include a Schiff-base-type ligand derived from a chiral diamino building block, and a binuclear transition metal core, each which can be varied for selectivity. The metal core is a Lewis-acidic metal ion, such as copper, zinc, lanthanum, iron and nickel. The Schiff-base may be a reduced or non-reduced Schiff-base derived from aliphatic linear, aliphatic cyclic diamino alcohols or aromatic aldehydes. The ligand can be a penta- or heptadentate ligand derived from pyridinecarbaldehydes, benzaldehydes, linear or cyclic diamines or diamino alcohols.

  本文公开了一类用于立体选择性水解糖类和苷类的手性双核金属配合物，尤其是手性双核过渡金属配合物催化剂，该催化剂可在接近生理 pH 值的水溶液中分辨糖类的外嵌糖苷和 α 和 β-糖苷键。手性双核金属配合物包括一个由手性二氨基结构单元衍生的希夫碱配体和一个双核过渡金属核心，每个配体的选择性都可以改变。金属核为路易斯酸性金属离子，如铜、锌、镧、铁和镍。希夫碱可以是还原型或非还原型希夫碱，由脂肪族线性、脂肪族环状二元醇或芳香族醛衍生而来。配体可以是五齿或七齿配体，由吡啶羧醛、苯醛、线性或环状二胺或二元醇衍生而来。
• Target Selectivity of FimH Antagonists
  作者：Meike Scharenberg、Oliver Schwardt、Said Rabbani、Beat Ernst

  DOI：10.1021/jm3010338

  日期：2012.11.26

  Mannose-based FimH antagonists are considered new therapeutics for the treatment of urinary tract. infections (UTIs). They prevent the adhesion of uropathogenic Escherichia coli (UPEC) to urothelial cell surfaces triggered by the lectin FimH, which is located at the tip of bacterial type I pili. Because all reported FimH antagonists are alpha-D-mannosides, they are also potential ligands of mannose receptors of the human host system. We therefore investigated the selectivity range of five FimH antagonists belonging to different compound families by comparing their affinities for FimH and eight human mannose receptors. On the basis of the detected selectivity range of approximately 5 orders of magnitude, no adverse side effects resulting from nonselective binding to the human receptors have to be expected. FimH antagonists can therefore be further considered as potential therapeutics for the., treatment of UTI.
• CHIRAL BINUCLEAR METAL COMPLEXES FOR STEREOSELECTIVE HYDROLYSIS OF SACCHARIDES AND GLYCOSIDES
  申请人：BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS

  公开号：US20210101138A1

  公开（公告）日：2021-04-08

  Disclosed herein is a class of chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides, and more particular chiral binuclear transition metal complex catalysts that discriminate epimeric glycosides and α- and β-glycosidic bonds of saccharides in aqueous solutions at near physiological pHs. The chiral binuclear metal complexes include a Schiff-base-type ligand derived from a chiral diamino building block, and a binuclear transition metal core, each which can be varied for selectivity. The metal core is a Lewis-acidic metal ion, such as copper, zinc, lanthanum, iron and nickel. The Schiff-base may be a reduced or non-reduced Schiff-base derived from aliphatic linear, aliphatic cyclic diamino alcohols or aromatic aldehydes. The ligand can be a penta- or heptadentate ligand derived from pyridinecarbaldehydes, benzaldehydes, linear or cyclic diamines or diamino alcohols.