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Org Biomol Chem
2011 Jan 07;91:278-90. doi: 10.1039/c0ob00396d.
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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.
Moreau C
,
Ashamu GA
,
Bailey VC
,
Galione A
,
Guse AH
,
Potter BV
.
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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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