Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles
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
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.
carbohydrates, glyconanomaterials, coupling chemistry, perfluoroaryl azides, F-19 qNMR
IdentifiersURN: urn:nbn:se:kth:diva-196604DOI: 10.1021/acsami.6b07471ISI: 000385992400081ScopusID: 2-s2.0-84992189531OAI: oai:DiVA.org:kth-196604DiVA: diva2:1047708
QC 201611182016-11-182016-11-172016-11-18Bibliographically approved