Glycopolymeric inhibitors of β-glucuronidase I. Synthesis and polymerization of styrene derivatives having pendant D-glucaric moieties

✍ Scribed by Kazuhiko Hashimoto; Ryo Ohsawa; Naohiro Imai; Masahiko Okada

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 249 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990201)37:3<303::aid-pola7>3.0.co;2-4

✦ Synopsis

Two kinds of novel vinyl monomers having D-glucaric moieties leading to a new type of glycopolymeric inhibitors of ␤-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°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 ␤-glucuronidase strongly through a model reaction with p-nitrophenyl ␤-D-glucuronide (10) in acetic buffer solution (pH 4.7).