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Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles
A new conjugation method for the immobilization of carbohydrates on
nanomaterials was demonstrated simply by mixing perfluorophenyl azide-functionalized
silica nanoparticles (SNPs), an amine-derivatized carbohydrate, and phenylacetaldehyde
under ambient conditions without any catalyst. The density of carbohydrates on the
glyconanoparticles was determined using the quantitative 19F NMR (19F qNMR)
technique; for example, the density of D-mannose (Man) on Man-SNPs was 2.5 ± 0.2 ×
10¿16 nmol/nm2. The glyconanoparticles retained their binding affinity and selectivity
toward cognate lectins. The apparent dissociation constant of the glyconanoparticles was
measured by a fluorescence competition assay, where the binding affinity of Man-SNPs
was almost 4 orders of magnitude higher than that of Man with concanavalin A. Moreover,
even with a ligand density of 2.6 times lower than Man-SNPs synthesized by the coppercatalyzed
azide¿alkyne cycloaddition, the binding affinity of Man-SNPs prepared by the
current method was more than 4 times higher.
KEYWORDS: carbohydrates, glyconanomaterials, couplingPeer Reviewe