8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides.
8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides.
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8-羟基喹啉作为人工受体的构建模块：吡喃糖苷识别中的结合偏好
DOI：
10.1039/c0ob00960a
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发表时间：
2011
影响因子：
3.2
通讯作者：
C. Geffert
中科院分区：
文献类型：
--
作者：
M. Mazik;C. Geffert
制备了含有三取代三乙苯核的8-羟基喹啉受体1-3，并对其与糖苷的结合性能进行了评价。1H NMR和荧光滴定以及两相体系的结合研究，如固体碳水化合物在极性介质中的溶解和糖从水溶液到有机溶剂的相转移，揭示了β-与α-异头体在苷识别中的结合偏好。与先前描述的三臂氨基吡啶受体相比，化合物1和2对β-半乳糖苷的亲和力显著增加。受体2包含两个8-羟基喹啉单位，被证明是β-半乳糖苷最有效的受体。含有一个8-羟基喹啉基团的化合物3是β-葡萄糖苷的高效受体，并且比以喹啉为基础的化合物4的受体更强，这表明喹啉羟基在络合物的形成中起着重要的作用。
8-Hydroxyquinoline-based receptors 1–3, containing a trisubstituted triethylbenzene core, were prepared and their binding properties towards glycosides were evaluated. 1H NMR and fluorescence titrations as well as binding studies in two-phase systems, such as dissolution of solid carbohydrates in apolar media and phase transfer of sugars from aqueous into organic solvents, revealed β- vs. α-anomer binding preferences in the recognition of glycosides. Compared to the previously described three-armed aminopyridine-based receptor, compounds 1 and 2 showed significantly increased affinity to β-galactoside. Receptor 2, incorporating two 8-hydroxyquinoline units, was shown to be the most effective receptor for β-galactoside. Compound 3, bearing one 8-hydroxyquinoline group, was found to be a highly effective receptor for β-glucoside and shown to be a more powerful receptor than the quinoline-based compound 4, indicating an important role of the quinoline hydroxy group in the complex formation.
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