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As a stable analog of the second messenger cyclic ADP-ribose (cADPR), we designed 4″-azidoethyl-cyclic ADP-carbocylic-ribose (N3-cADPcR). For the synthesis of N3-cADPcR, 1β-amino-2,3-O-isoproplylidene-4α-azidoethyl carbocyclic-ribose (4) having a chiral quaternary stereogenic center is required as the key unit. We successfully synthesized the desired unit 4 via construction of the quaternary stereogenic...
We previously showed that 3″-deoxy-cyclic ADP-carbocyclic-ribose (3″-deoxy-cADPcR, 4) is a stable and highly potent analogue of cyclic ADP-ribose (cADPR, 1), a Ca 2+ -mobilizing second messenger. From these results, we designed and synthesized other 3″-modified analogues of cADPcR having a substituent at the 8-position and found that this modification at the 8-position made them partial agonists...
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