Synthesis of sugar-containing hydrophilic porous polymer supports via suspension polymerization

Abstract

Using different porogens and crosslinkers for 3-O-methacryloyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose, porous polymer beads having surface areas of up to 300 m²g^–1 were synthesized by suspension polymerization. After subsequent removal of the protecting groups, a hydrophilic sugar-containing resin was obtained. In the case when the initial polymer had only very small pores, after hydrolysis, an almost non-porous resin was recovered. With initially large pores, the pore structure of the resin remained unchanged. For resins with medium pore sizes, the pore volume and surface area of the unprotected resin were dependent of the degree of hydrolysis. In fact a linear relationship between surface area and degree of hydrolysis could be observed. Furthermore, this relationship was reversible, i. e. after reprotection of partly or fully hydrolyzed resins, the original pore structure of the protected polymer could be recovered. Depending on the degree of hydrolysis, porous resins of various hydrophilicity, containing reactive hydroxyl groups suitable for further derivatization have been synthesized.