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Stable cyclic adenosine 5'-diphosphate ribose (cADPR) analogues are chemical biology tools that can probe the Ca(2+) release mechanism and structure-activity relationships of this emerging potent second messenger. However, analogues with an intact "northern" ribose have been inaccessible due to the difficulty of generating the sensitive N1-ribosyl link. We report the first total synthesis of the membrane permeant, hydrolytically stable, cADPR receptor agonist 8-Br-N1-cIDPR via regio- and stereoselective N1-ribosylation of protected 8-bromoinosine.

Original publication

DOI

10.1021/jo202319f

Type

Journal article

Journal

J Org Chem

Publication Date

04/05/2012

Volume

77

Pages

4191 - 4197

Keywords

Calcium, Cyclic ADP-Ribose, Humans, Jurkat Cells, Stereoisomerism, Structure-Activity Relationship