Abstract
3-O-β-D-Glucopyranosiduronyl-D-glucaro-1, 4-lactone (VI), a new masked inhibitor of β-glucuronidase, was synthesized by the fusion of dimethyl 2, 4-O-benzylidene-5-O-acetyl-D-glucarate (I) and methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate (II) in the presence of mercuric cyanide, followed by removal of the protecting groups and lactonization. The chemical structure of VI was confirmed to be 3-O-β-D-glucopyranosiduronyl-D-glucaro-1, 4-lactone from the chemical and physical data of the products (III, IV, V, and VI) obtained in the course of its synthesis. The inhibitory effect of VI on β-glucuronidase in vitro was also examined.
