PURIN-6-YL 6-DEOXY-1-THIO-β-D-GLUCOPYRANOSIDE. ENZYMOLOGY, CHEMISTRY, AND CYTOTOXICITY

Article abstract of DOI:10.1016/0008-6215(87)80106-4

Purin-6-yl 6-deoxy-1-thio-β-D-glucopyranoside (4) is a substrate for almond β-glucosidase and a weak competitive inhibitor of bovine liver β-D-glucuronidase (K_i ca. 20mM).Both 4 and purine-protonated 4 undergo hydrolysis catalyzed by dilute acid in the pH range 0.17-2.59.These results are compared with those previously obtained with ammonium (purin-6-yl 1-thio-β-D-glucopyranosid)uronate, (purin-6-yl 1-thio-β-D-glucopyranosid)uronamide, purin-6-yl 1-thio-β-D-glucopyranoside, and purin-6-yl 2-deoxy-1-thio-β-D-glucopyranoside, and it is concluded that the data support an involvement of substituents at C-5 in producing productive Mi chaelis-complex conformers.The 6-deoxyglucoside is more active than the D-glucosiduronic acid in an L1210 mouse screen.