Design and synthesis of 4″,6″-unsaturated cyclic ADP-carbocyclic ribose as a Ca<sup>2+</sup>-mobilizing agent
Kudoh T., Weber K., Guse AH., Potter BVL., Hashii M., Higashida H., Arisawa M., Matsuda A., Shuto S.
4″,6″-Didehydro-cADPcR (3), an unsaturated carbocyclic ribose analog of a Ca 2+ -mobilizing second messenger cyclic ADP-ribose (cADPR), was designed and successfully synthesized using a key intramolecular condensation reaction forming the 18-membered pyrophosphate ring structure with a S-phenyl phosphorothioate-type substrate. Biological evaluation showed that 4″,6″-didehydro-cADPcR is a potent Ca 2+ -mobilizing agent in T cells. © 2008 Elsevier Ltd. All rights reserved.