Selective inhibition of gastrointestinal beta-glucuronidase by polyvinylbenzyl D-glucaro(1,4)lactonate: attachment of D-glucaro(1,4)lactone to polyvinylbenzyl chloride.
D-Glucaro(1,4)lactone, a potent beta-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 degrees C for 7 d in the presence of a catalyst, caesium iodide.
Sacco
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Environmental Health Sciences Program, School of Public Health, University of Massachusetts, Amherst 01003.
McEwen
W E
WE
Calabrese
E J
EJ
D002586:Cesium / Q000737:chemistry; D004064:Digestive System / Q000201:enzymology*; D005937:Glucaric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D005966:Glucuronidase / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D011145:Polyvinyls / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared
D011145:Polyvinyls; C080605:polyvinylbenzyl glucaro(1,4)lactonate; D002586:Cesium; C009194:saccharolactone; C080604:polyvinylbenzyl chloride; D005966:Glucuronidase; D005937:Glucaric Acid