Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor

Novel 8-substituted base and sugar-modified analogues of the Ca(2+) mobilizing second messenger cyclic adenosine 5′-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational an...

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Autores principales: Moreau, Christelle, Ashamu, Gloria A., Bailey, Victoria C., Galione, Antony, Guse, Andreas H., Potter, Barry V. L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2011
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3172588/
https://www.ncbi.nlm.nih.gov/pubmed/20976353
http://dx.doi.org/10.1039/c0ob00396d
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author Moreau, Christelle
Ashamu, Gloria A.
Bailey, Victoria C.
Galione, Antony
Guse, Andreas H.
Potter, Barry V. L.
author_facet Moreau, Christelle
Ashamu, Gloria A.
Bailey, Victoria C.
Galione, Antony
Guse, Andreas H.
Potter, Barry V. L.
author_sort Moreau, Christelle
collection PubMed
description Novel 8-substituted base and sugar-modified analogues of the Ca(2+) mobilizing second messenger cyclic adenosine 5′-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by (1)H NMR spectroscopy revealed that a C2′ endo/syn conformation of the “southern” ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor.
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spelling pubmed-31725882011-09-26 Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor Moreau, Christelle Ashamu, Gloria A. Bailey, Victoria C. Galione, Antony Guse, Andreas H. Potter, Barry V. L. Org Biomol Chem Chemistry Novel 8-substituted base and sugar-modified analogues of the Ca(2+) mobilizing second messenger cyclic adenosine 5′-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by (1)H NMR spectroscopy revealed that a C2′ endo/syn conformation of the “southern” ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor. Royal Society of Chemistry 2011-01-07 2010-10-25 /pmc/articles/PMC3172588/ /pubmed/20976353 http://dx.doi.org/10.1039/c0ob00396d Text en This journal is © The Royal Society of Chemistry 2010 http://creativecommons.org/licenses/by-nc/2.0/uk/ This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Moreau, Christelle
Ashamu, Gloria A.
Bailey, Victoria C.
Galione, Antony
Guse, Andreas H.
Potter, Barry V. L.
Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor
title Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor
title_full Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor
title_fullStr Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor
title_full_unstemmed Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor
title_short Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor
title_sort synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a c2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cadpr receptor
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3172588/
https://www.ncbi.nlm.nih.gov/pubmed/20976353
http://dx.doi.org/10.1039/c0ob00396d
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