Abstract
Potential affinity probes for adenylyl cyclase were synthesized that take advantage of the enzyme's sensitivity to “P”-site-mediated inhibition by 2′,5′-dideoxyadenosine analogs and its tolerance for large 3′-ribose substitutions. We report the synthesis of a series of 3′-substituted 2′,5′-dideoxyadenosine analogs. The syntheses involved the intermediate formation of symmetric anhydrides that were then coupled to 2′,5′-dideoxyadenosine by base-catalyzed esterification at the 3′-ribose position.