화학공학소재연구정보센터
Journal of Polymer Science Part A: Polymer Chemistry, Vol.37, No.3, 303-312, 1999
Glycopolymeric inhibitors of beta-glucuronidase I. Synthesis and polymerization of styrene derivatives having pendant D-glucaric moieties
Two kinds of novel vinyl monomers having D-glucaric moieties leading to a new type of glycopolymeric inhibitors of beta-glucuronidase, N-p-vinylbenzyl-6-D-glucaramide (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 degrees C in 0.1 N 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 p-glucuronidase strongly through a model reaction with p-nitrophenyl beta-D-glucuronide (10) in acetic buffer solution (pH 4.7).