Synthetic study on carbocyclic analogs of cyclic ADP-ribose, a novel second messenger: an efficient synthesis of cyclic IDP-carbocyclic-ribose.
An efficient synthesis of cyclic IDP-carbocyclic-ribose, as a stable mimic for cyclic ADP-ribose, was achieved. 8-Bromo-N1-carbocyclic-ribosylinosine derivative 10, prepared from N1-(2,4-dinitrophenyl)inosine derivative 5 and an optically active carbocyclic amine 6, was converted to 8-bromo-N1-carbocyclic-ribosylinosine bisphosphate derivative 15. Treatment of 15 with I2 in the presence of molecular sieves in pyridine gave the desired cyclic product 16 quantitatively, which was deprotected and reductively debrominated to give the target cyclic IDP-carbocyclic-ribose (3).
Fukuoka
M
M
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Shuto
S
S
Minakawa
N
N
Ueno
Y
Y
Matsuda
A
A
D000246:Adenosine Diphosphate Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D036563:Cyclic ADP-Ribose; D015195:Drug Design; D007202:Indicators and Reagents; D007290:Inosine Diphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007292:Inosine Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D015290:Second Messenger Systems
D007202:Indicators and Reagents; D007292:Inosine Nucleotides; C107267:cyclic IDP-ribose; D036563:Cyclic ADP-Ribose; D000246:Adenosine Diphosphate Ribose; D007290:Inosine Diphosphate