A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water.
A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water.
复制标题
选择性识别水中单糖和低聚糖的通用方法。
DOI：
10.1021/jacs.6b10773
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发表时间：
2017-01-18
影响因子：
15
通讯作者：
Zhao Y
中科院分区：
文献类型：
--
作者：
Gunasekara RW;Zhao Y
碳水化合物的分子识别在生物学中起着至关重要的作用，但很难用人工合成的受体来实现。通过碳水化合物的共价印迹在硼罗索功能化交联胶束中，我们制备了多种单糖和低聚糖的纳米颗粒受体。硼唑功能单体通过顺式1,2-二醇、顺式3,4-二醇和反式4,6-二醇结合糖模板。蛋白质大小的纳米颗粒对水中具有亚毫摩尔结合亲和力的d -醛己糖具有优异的选择性，并完全区分了三种生物学上重要的己糖（葡萄糖、甘露糖和半乳糖）。由于疏水相互作用增强，糖苷与非极性糖基表现出更强的结合。低聚糖是根据它们的单糖构建块、糖苷键、链长以及可以与纳米颗粒相互作用的附加官能团来区分的。
Molecular recognition of carbohydrates plays vital roles in biology but has been difficult to achieve with synthetic receptors. Through covalent imprinting of carbohydrates in boroxole-functionalized cross-linked micelles, we prepared nanoparticle receptors for a wide variety of mono- and oligosaccharides. The boroxole functional monomer bound the sugar templates through cis-1,2-diol, cis-3,4-diol, and trans-4,6-diol. The protein-sized nanoparticles showed excellent selectivity for D-aldohexoses in water with submillimolar binding affinities and completely distinguished the three biologically important hexoses (glucose, mannose, and galactose). Glycosides with nonpolar aglycon showed stronger binding due to enhanced hydrophobic interactions. Oligosaccharides were distinguished based on their monosaccharide building blocks, glycosidic linkages, chain length, as well as additional functional groups that could interact with the nanoparticles.