Synthetic study on carbocyclic analogues of cyclic ADP-ribose.
Cyclic ADP-ribose (cADPR, 1) is a newly discovered general mediator involved in Ca2+ signaling. Carbocyclic analogues of 1, namely, 2 and 3, were designed as a stable isosteres of 1, and their synthesis was studied. The reaction of a triflate 9 which was derived from known diol 4, and inosine derivative 10 gave desired N1-alkyl derivative 11 in 38% yield, and then it was converted to diphosphate derivative 12.
Shirato
M
M
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Shuto
S
S
Ueno
Y
Y
Matsuda
A
A
D000246:Adenosine Diphosphate Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D002118:Calcium / Q000378:metabolism; D036563:Cyclic ADP-Ribose; D007424:Intracellular Fluid; D008722:Methods; D008968:Molecular Conformation; D015394:Molecular Structure; D015290:Second Messenger Systems
D036563:Cyclic ADP-Ribose; D000246:Adenosine Diphosphate Ribose; D002118:Calcium