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Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
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2016 (English)In: ACS Applied Materials and Interfaces, ISSN 1944-8244, E-ISSN 1944-8252, Vol. 8, no 41, 28136-28142 p.Article in journal (Refereed) Published
Abstract [en]

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 F-19 NMR (F-19 qNMR) technique; for example, the density of D-mannose (Man) on Man-SNPs was 2.5 +/- 0.2 x 10(-16) nmol/nm(2). 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.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 8, no 41, 28136-28142 p.
Keyword [en]
carbohydrates, glyconanomaterials, coupling chemistry, perfluoroaryl azides, F-19 qNMR
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-196604DOI: 10.1021/acsami.6b07471ISI: 000385992400081Scopus ID: 2-s2.0-84992189531OAI: oai:DiVA.org:kth-196604DiVA: diva2:1047708
Note

QC 20161118

Available from: 2016-11-18 Created: 2016-11-17 Last updated: 2016-11-18Bibliographically approved

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