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Reference type: Journal
Authors: Gunasekara RW, Zhao Y
Article Title: A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water.
Publication date: 2017
Journal: Journal of the American Chemical Society
Volume: 139
Issue: (2)
Page numbers: 829-835.
DOI: 10.1021/jacs.6b10773

Abstract: 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 on the basis of their monosaccharide building blocks, glycosidic linkages, chain length, as well as additional functional groups that could interact with the nanoparticles
Template and target information: monosaccharides, d-aldohexoses, glucose, mannose, galactose, oligosaccharides


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