Glycopolymeric inhibitors of ?-glucuronidase. II. Synthesis of glycopolymers containing pendantL-gulonic moieties and effects of the carboxyl group in the glycopolymers upon the activity of ?-glucuronidase

Abstract

A new styrene derivative having an L-gulonic moiety, N-(p-vinylbenzyl)-6-L-gulonamide (VB-6-Glco, 3) was synthesized from L-gulono-1,4-lactone and p-vinylbenzylamine. The styrene derivative (3) was subjected to the radical homopolymerization and copolymerization with acrylamide and acrylic acid. The hydrolysis of p-nitrophenyl β-D-glucuronide with β-glucuronidase was scarcely inhibited in the presence of the glycopolymer prepared from 3 and acrylamide (P(VB-6-Glco-co-AAm), 4), whereas the glycopolymer prepared from 3 and acrylic acid (P(VB-6-Glco-co-AAK), 5) was found to suppress the enzyme activity strongly as well as a polystyrene derivative having pendant D-glucaric moieties (P(VB-6-GlcaH-co-AAm), 6). From the kinetic analysis of the hydrolysis, the glycopolymers 6 and 5 were postulated to inhibit the enzyme competitively and uncompetitively, respectively. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 2773–2779, 1999