Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist

[Image: see text] 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 inacce...

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Autores principales: Swarbrick, Joanna M., Potter, Barry V. L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2012
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3343700/
https://www.ncbi.nlm.nih.gov/pubmed/22283398
http://dx.doi.org/10.1021/jo202319f
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author Swarbrick, Joanna M.
Potter, Barry V. L.
author_facet Swarbrick, Joanna M.
Potter, Barry V. L.
author_sort Swarbrick, Joanna M.
collection PubMed
description [Image: see text] 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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spelling pubmed-33437002012-05-04 Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist Swarbrick, Joanna M. Potter, Barry V. L. J Org Chem [Image: see text] 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. American Chemical Society 2012-01-25 2012-05-04 /pmc/articles/PMC3343700/ /pubmed/22283398 http://dx.doi.org/10.1021/jo202319f Text en Copyright © 2012 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Swarbrick, Joanna M.
Potter, Barry V. L.
Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist
title Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist
title_full Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist
title_fullStr Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist
title_full_unstemmed Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist
title_short Total Synthesis of a Cyclic Adenosine 5′-Diphosphate Ribose Receptor Agonist
title_sort total synthesis of a cyclic adenosine 5′-diphosphate ribose receptor agonist
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3343700/
https://www.ncbi.nlm.nih.gov/pubmed/22283398
http://dx.doi.org/10.1021/jo202319f
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