Campus Units
Chemistry
Document Type
Article
Publication Version
Accepted Manuscript
Publication Date
2017
Journal or Book Title
Journal of the American Chemical Society
Volume
139
Issue
2
First Page
829
Last Page
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.
Copyright Owner
American Chemical Society
Copyright Date
2016
Language
en
File Format
application/pdf
Recommended Citation
Gunasekara, Roshan W. and Zhao, Yan, "A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water" (2017). Chemistry Publications. 1093.
https://lib.dr.iastate.edu/chem_pubs/1093
Included in
Materials Chemistry Commons, Nanoscience and Nanotechnology Commons, Organic Chemistry Commons
Comments
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see DOI: 10.1021/jacs.6b10773. Posted with permission.