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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.

SUBMITTER: Swarbrick JM

PROVIDER: S-EPMC3343700 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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

Swarbrick Joanna M JM Potter Barry V L BV

The Journal of organic chemistry 20120131 9

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 stereos ...[more]

PMID: 22283398

Similar Datasets

Cyclic adenosine 5'-diphosphate ribose analogs without a "southern" ribose inhibit ADP-ribosyl cyclase-hydrolase CD38.

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Synthesis of Terminal Ribose Analogues of Adenosine 5'-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2.

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Ticagrelor inverse agonist activity at the P2Y<sub>12</sub> receptor is non-reversible versus its endogenous agonist adenosine 5´-diphosphate.

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| S-EPMC5489420 | biostudies-literature

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| S-EPMC5564845 | biostudies-literature

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