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Journal of Lipid Research, Vol 26, 1277-1282, Copyright © 1985 by Lipid Research, Inc.

ARTICLES

Chemical synthesis of all-trans retinoyl beta-glucuronide

AB Barua and JA Olson

All-trans retinoyl fluoride reacts with the 3,6-lactone of glucuronic acid in slightly alkaline solution to give the lactone of retinoyl beta- glucuronide, along with other retinoyl glucurono-lactones, in about 60% yield. Hydrolysis of the lactone with very dilute alkali gives the free acid, retinoyl beta-glucuronide, in about 80% yield. Pure all-trans retinoyl beta-glucuronide (overall yield: 20-25%) was obtained free from other isomeric and anomeric forms by reverse-phase high pressure liquid chromatography. Retinoyl beta-glucuronide was characterized by UV-visible, infrared, and 1H-NMR spectra, by elementary analysis, by mass spectra, and by its susceptibility to hydrolysis by bacterial beta- glucuronidase.
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				A. B. Barua and N. Sidell Retinoyl {beta}-Glucuronide: A Biologically Active Interesting Retinoid J. Nutr., January 1, 2004; 134(1): 286S - 289. [Abstract] [Full Text] [PDF]