Synthesis of a New Polymer Containing Uridine and Galactose as Pendent Groups

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Abstract
A new styrene compound containing a derivatized undine unit, that is, 2′,3′-O-isopropylideneuridine 5′-p-styrenesulfonate (1), was synthesized and polymerized with AIBN as an initiator. Removal of protecting isopropylidene groups from the obtained polymer gave uridine-containing polystyrene. Uridine-containing polystyrene was synthesized also by the polymerization of the deprotected monomer (2), which had been prepared by removal of isopropylidene group from 1. Copolymerization of 1 with a styrene monomer having a galactosyl moiety, that is, N-p-vinylbenzyl-4-O-(β- d -galactopyranosy)- d -gluconamide1 (3), was carried out in dimethyl sulfoxide. However, the deprotection of the obtained copolymer failed, because the lactonamide portion was severed in the process of deisopropylidenation. On the other hand, the copolymerization of 2 with 3 in dimethylformamide and in water with AIBN as an initiator gave the target copolymer which contained both uridine and galactose residues. Polymers and copolymers were characterized by 1H NMR spectroscopy.