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Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles.

Kong, Na; Xie, Sheng; Zhou, Juan; Menéndez, Margarita; Solís, Dolores; Park, JaeHyeung; Proietti, Giampiero; Ramström, Olof; Yan, Mingdi.
Artigo em Inglês | MEDLINE | ID: mdl-27649792
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 copper-catalyzed azide-alkyne cycloaddition, the binding affinity of Man-SNPs prepared by the current method was more than 4 times higher.
Selo DaSilva