title: Total synthesis of a cyclic adenosine 5'-diphosphate ribose receptor agonist.
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.
authors.affiliation: Wolfson Laboratory of Medicinal Chemistry, University of Bath, Department of Pharmacy and Pharmacology, Claverton Down, Bath BA2 7AY, UK.
authors.forename: Joanna M
authors.initials: JM
authors.lastname: Swarbrick
authors.forename: Barry V L
authors.initials: BV
authors.lastname: Potter
mesh_terms: D002118:Calcium / Q000737:chemistry* / Q000378:metabolism*; D036563:Cyclic ADP-Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D006801:Humans; D019169:Jurkat Cells / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D036563:Cyclic ADP-Ribose; D002118:Calcium