Chemical synthesis of all-trans retinoyl beta-glucuronide.

Chemical synthesis of all-trans retinoyl beta-glucuronide.

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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 verona wig 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 cent dyyni UV-visible, infrared, and 1H-NMR spectra, by elementary analysis, by mass spectra, and by its susceptibility to hydrolysis by bacterial beta-glucuronidase.