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

Reference:

Swarbrick, J. M. and Potter, B. V. L., 2012. Total synthesis of a cyclic adenosine 5′-diphosphate ribose receptor agonist. Journal of Organic Chemistry, 77 (9), pp. 4191-4197.

Related documents:

Official URL:

http://dx.doi.org/10.1021/jo202319f

Related URLs:

• http://dx.doi.org/10.1021/jo202319f

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.

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