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Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles

AuthorsKong, N.; Xie, S.; Zhou, J.; Menéndez, Margarita ; Solís, Dolores; Park, J.; Ramström, O; Yan, M
Issue Date2016
CitationACS Applied Materials and Interfaces 8: 28136- 28142 (2016)
AbstractA 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, coupling
Identifiersdoi: 10.1021/acsami.6b07471
issn: 1944-8252
Appears in Collections:(IQFR) Artículos
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