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Original Articles

Synthesis of Iodo-aryl-azido Adenosine Analogs as Affinity Ligands for Adenylyl Cyclase

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Pages 1977-1989 | Received 17 Feb 1994, Accepted 21 Jun 1994, Published online: 24 Sep 2006
 

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.

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