title: Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles.
abstract: 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 quantitative19F NMR (19F qNMR) technique; for example, the density of d-mannose (Man) on Man-SNPs was 2.5 ± 0.2 × 10-16nmol/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.
authors.affiliation: Department of Chemistry, KTH-Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
authors.forename: Na
authors.initials: N
authors.lastname: Kong
authors.affiliation: Department of Chemistry, KTH-Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
authors.forename: Sheng
authors.initials: S
authors.lastname: Xie
authors.affiliation: Department of Chemistry, KTH-Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
authors.forename: Juan
authors.initials: J
authors.lastname: Zhou
authors.affiliation: Instituto de Química Física Rocasolano , Consejo Superior de Investigaciones Científicas, and Centro de Investigación Biomédica en Red de Enfermedades Respiratorias (CIBERES), ISCIII, Madrid, Spain.
authors.forename: Margarita
authors.initials: M
authors.lastname: Menéndez
authors.affiliation: Instituto de Química Física Rocasolano , Consejo Superior de Investigaciones Científicas, and Centro de Investigación Biomédica en Red de Enfermedades Respiratorias (CIBERES), ISCIII, Madrid, Spain.
authors.forename: Dolores
authors.initials: D
authors.lastname: Solís
authors.affiliation: Department of Chemistry, University of Massachusetts Lowell , 1 University Avenue, Lowell, Massachusetts 01854, United States.
authors.forename: JaeHyeung
authors.initials: J
authors.lastname: Park
authors.affiliation: Department of Chemistry, KTH-Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
authors.forename: Giampiero
authors.initials: G
authors.lastname: Proietti
authors.affiliation: Department of Chemistry, KTH-Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
authors.forename: Olof
authors.initials: O
authors.lastname: Ramström
authors.affiliation: Department of Chemistry, KTH-Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.|Department of Chemistry, University of Massachusetts Lowell , 1 University Avenue, Lowell, Massachusetts 01854, United States.
authors.forename: Mingdi
authors.initials: M
authors.lastname: Yan
keywords: 19F qNMR; carbohydrates; coupling chemistry; glyconanomaterials; perfluoroaryl azides