Glycopolymeric inhibitors of ?-glucuronidase I. Synthesis and polymerization of styrene derivatives having pendantD-glucaric moieties

Abstract

Two kinds of novel vinyl monomers having D-glucaric moieties leading to a new type of glycopolymeric inhibitors of β-glucuronidase, N-p-vinylbenzyl-6-D-glucar-amide (6) and potassium N-p-vinylbenzyl-6-D-glucaramid-1-ate (8), were synthesized by the reaction of D-glucaro-6,3-lactone (3) with p-vinylbenzylamine (5) with no catalyst, and the subsequent treatment of the reaction mixture with acetic anhydride and potassium hydroxide aqueous solution, respectively. The radical copolymerization of 8 with acrylamide in various feed ratios at 60°C in 0.1N potassium chloride aqueous solution gave water-soluble copolymers (9) composed of a synthetic polymeric main chain and many pendant D-glucaric chains. The resulting glycopolymers (9) were found to inhibit the activity of β-glucuronidase strongly through a model reaction with p-nitrophenyl β-D-glucuronide (10) in acetic buffer solution (pH 4.7).