Glyconanoparticles are emerging probes for unravelling complex carbohydrate-carbohydrate or carbohydrate-protein interactions [1]. Gold glyconanoparticles consist of an inorganic core of Au0surrounded by an organic shell comprising a linker region to which carbohydrate ligands are attached.The correct presentation of carbohydrate ligands on the surface of nanoparticles reflects a balance between optimal multivalent display of the glycan ligands for their interaction partners and suitable physico-chemical properties of the nanoparticles that confers biocompatibility. To this end, we have designed linkers for self-assembly on gold glyconanoparticles that are flexible yet allow controlled physical repositioning of the glycan ligands within the organic shell. Incorporation of azobenzene units into the linkers facilitates a reversible transition between E- and Z- configurations by near-UV irradiation that affects a reorganization of the linkers [2]. When assembled on nanoparticle surfaces these linkers may cause steric diversion or contraction of the glycan display, e.g., that can lead to formation or breaking of weak interactions of the ligands.We report here our initial findings in assembling and evaluating this novel class of glyconanoparticles using azobenzene-linked a-mannosides.[1] Larsen, K.; Thygesen, M. B.; Guillaumie, F.; Willats, W. G. T.; Jensen, K. J. Solid-phase chemical tools for glycobiology, Carbohydr. Res. 2006  , 341, 1209-1234.[2] Chandrasekaran, V.; Lindhorst, T. K. Sweet switches: azobenzene glycoconjugates synthesized by click chemistry, Chem. Commun. 2012  , 48, 7519-7521.

Photo-switchable glycan ligands on gold nanoparticles

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.