TY - JOUR
T1 - Generating Selective Saccharide Binding Affinity of Phenyl Boronic Acids by using Single-Walled Carbon Nanotube Corona Phases
AU - Mu, Bin
AU - Ahn, Jiyoung
AU - McNicholas, Thomas P.
AU - Strano, Michael S.
N1 - Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/3/16
Y1 - 2015/3/16
N2 - 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 phenylboronic 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.
AB - 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 phenylboronic 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.
KW - Cophmores
KW - Molecular recognition
KW - Nanotubes
KW - Phenylboronic acid
KW - Sensors
UR - http://www.scopus.com/inward/record.url?scp=84924079899&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84924079899&partnerID=8YFLogxK
U2 - 10.1002/chem.201500175
DO - 10.1002/chem.201500175
M3 - Article
C2 - 25644377
AN - SCOPUS:84924079899
SN - 0947-6539
VL - 21
SP - 4523
EP - 4528
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 12
ER -