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

  • Org Biomol Chem. 2011 Jan 7;9(1):278-90. doi: 10.1039/c0ob00396d.
Christelle Moreau  1 ,  Gloria A Ashamu ,  Victoria C Bailey ,  Antony Galione ,  Andreas H Guse ,  Barry V L Potter
Affiliations
  • 1. Wolfson Laboratory of Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Bath, UK BA2 7AY.
PMID: 20976353 DOI: 10.1039/c0ob00396d
Abstract

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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