Issue 1, 2011
From the journal:

Organic & Biomolecular Chemistry

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  

* 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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Article information

DOI
https://doi.org/10.1039/C0OB00396D
Article type
Paper
Submitted
07 Jul 2010
Accepted
14 Sep 2010
First published
25 Oct 2010
This article is Open Access

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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