Generating Selective Saccharide Binding Affinity of Phenyl Boronic Acids by using Single-Walled Carbon Nanotube Corona Phases
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mit Chemistry European Fin 1 13 2015_light_mit.pdf
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Author(s)
Mu, Bin
Ahn, Jiyoung
McNicholas, Thomas P.
Strano, Michael S.
Date Issued
February 2015
Journal
Chemistry - A European Journal
Publisher
Wiley Blackwell
Citation
Mu, Bin, Jiyoung Ahn, Thomas P. McNicholas, and Michael S. Strano. “Generating Selective Saccharide Binding Affinity of Phenyl Boronic Acids by Using Single-Walled Carbon Nanotube Corona Phases.” Chem. Eur. J. 21, no. 12 (February 2, 2015): 4523–4528.
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Author's final manuscript
Abstract
Saccharides recognition is challenging due to their low affinity for substrates, yet this recognition is critical for human immunity and glycobiology. Herein, we demonstrate that a polymer or surfactant corona phase surrounding a single-walled carbon nanotube can substantially modify the selectivity of pre-adsorbed phenyl-boronic acids (PBA) for mono-, di-, and poly-saccharides. A library of 17 PBAs including carboxy, nitro, and amino PBA with ortho-, meta-, or para- substitutions are used to generate 144 distinct corona phases. Six in particular demonstrate significantly increased selectivity to specific saccharides including ribose (0.42 mol per total mol), arabinose (0.36), and glucose (0.25), but unusually diminished binding to fructose (0.02). Recognition proceeds by saccharide adsorption into the corona, followed by PBA reaction in a consecutive second order reaction. The results extend to larger saccharides, such as glycosaminoglycans, suggesting promise for protein glycosylation.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
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DOI of Published Version
https://doi.org/10.1002/chem.201500175
