Development of Separation Material for Saccharide on the Basis of Surface Imprinting Procedure

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Recognition and separation of saccharides have been the focus of much recent attention. Boronic acid is a powerful tool for this purpose since it can form a stable complex (cyclic ester) with saccharides, especially with those comprising a cis-diol group. On the other hand, microspheres from synthetic polymers have become of interest in functional materials development. In the present work, we have prepared polymer microspheres having phenylboronic acid groups on their surface and carried out their characterizations. The polymer microspheres were prepared by emulsion polymerization of stirene, butyl acrylate, and m-acrylamidophenylboronic acid. The microsphere was swollen in an alkaline aqueous suspension by adding methylethylketone so that phenylboronic acid sites in the resin would migrate out to the aqueous-organic interface in their ionized forms. D-Glucose was bound onto the microsphere while 1-methyl-alpha-D-glucoside was not, due to their different molecular structures. The adsorption of D-glucose was performed by complex (ester) formation between phenylboronic acid moiety and cis-diol group of D-glucose. Although some preliminary experiments and theoretical calculations were performed for introduction of the imprinting structure, we have not yet got the imprinted microspheres for a specific structure of saccharide with a good reproducibility. However, the data and calculations give a clue in understanding the chemical behaviors of phenylboronic acid-modified microspheres as well as the operational parameters in the preparation of saccharide-imprinted structures. The material is expected to be useful for separation and concentration of biological constituents comprising a cis-diol group, e.g., glyco-and nucleo proteins, nucleic acids as well as saccharides.