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Issue 1, 2011
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Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor

Christelle Moreau,a  Gloria A. Ashamu,a  Victoria C. Bailey,a  Antony Galione,b  Andreas H. Gusec  and  Barry V. L. Potter*a 
Author affiliations

* Corresponding authors

a Wolfson Laboratory of Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Bath, UK
E-mail: b.v.l.potter@bath.ac.uk
Fax: +44 1225 386114
Tel: +44 1225 386639

b Department of Pharmacology, University of Oxford, Mansfield Road, Oxford, UK

c Institute of Biochemistry and Molecular Biology I: Cellular Signal Transduction, University Medical Center Hamburg-Eppendorf, Germany

Abstract

Novel 8-substituted base and sugar-modified analogues of the Ca2+ 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 1H 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.

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

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Publication details

The article was received on 07 Jul 2010, accepted on 14 Sep 2010 and first published on 25 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00396D
Citation: Org. Biomol. Chem., 2011,9, 278-290
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    Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor

    C. Moreau, G. A. Ashamu, V. C. Bailey, A. Galione, A. H. Guse and B. V. L. Potter, Org. Biomol. Chem., 2011, 9, 278
    DOI: 10.1039/C0OB00396D

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