PURINE THIOGLYCOSIDES .I. S-GLYCOSIDES OF 6-MERCAPTOPURINE

The preparation of a series of S-glycosides of 6-mercaptopurine is described. Two routes of synthesis were employed, the reaction of a 6-halogenopurine with a thioglvcose derivative, and the reaction of 6-mercaptopurine with a halogenoacylated sugar, followed by deacylation. Thioglycoside configurations were assigned by analogy with known alkyl and aryl thioglycosides. The purine thioglycosides are readily oxidized to sulfones. 6-Purinyl α-D-glucothiopyranoside is hydrolvzed in acid solution, and in neutral solution by a previously unrecognized thioglycosidase which is widely distributed in plant and animal tissues. Several other purinyl thioglycosides also are substrates for this enzyme. © 1968, American Chemical Society. All rights reserved.