Total synthesis of a cyclic adenosine 5′-diphosphate ribose receptor agonist

Joanna M. Swarbrick, Barry V. L. Potter

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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 languageEnglish
Pages (from-to)4191-4197
JournalJournal of Organic Chemistry
Volume77
Issue number9
DOIs
Publication statusPublished - 2012

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