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Selective Inhibition of Gastrointestinal β-Glucuronidase by Polyvinylbenzyl D-glucaro(1,4)lactonate: Attachment of D-Glucaro(1,4)lactone to Polyvinylbenzyl Chloride

Environmental Health Sciences Program, School of Public Health

W.E. McEwen

Department of Chemistry, University of Massachusetts, Amherst, MA 01003, USA

E.J. Calabrese

Environmental Health Sciences Program, School of Public Health

D-Glucaro(1,4)lactone, a potent β-glucuronidase inhibitor was attached via the carboxylic acid moiety to polyvinylbenzyl chloride (PVBC) using a bimolecular nucleophilic displacement reaction, First, the caesium salt of D-glucaro(1,4)lactone was prepared by titrating the carboxylic acid to neutrality with aqueous caesium bicarbonate. The polyvinylbenzyl D-glucaro(1,4)lactonate was obtained in maximum yields of between 50 and 60% when caesium D-glucaro(1,4)lactonate was incubated with PVBC in DMF at 50°C for 7 d in the presence of a catalyst, caesium iodide.

Human & Experimental Toxicology, Vol. 12, No. 2, 181-184 (1993)
DOI: 10.1177/096032719301200216


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