Novel 3',5'-cyclic nucleotide analogue: adenosine 3',5'-cyclic boranomonophosphate.
A general procedure for the first synthesis of a 3',5'-cyclic boranomonophosphate was established. Specifically, adenosine 3',5'-cyclic boranomonophosphosphate (cyclic AMPB, 4c), a P-borane (BH(3)) analogue of adenosine 3',5'-cyclic monophosphate (cAMP), was synthesized via a phosphite approach in good yield. The method is also applicable for syntheses of natural cAMP and its phosphorothioate analogue. The two diasteromers of cyclic AMPB 4c were separated, and their chemical structures were established via spectroscopic methods.
Department of Chemistry, Box 90346, Duke University, Durham, North Carolina 27708-0346, USA.
J
J
Lin
K
K
He
B R
BR
Shaw
D001896:Boron Compounds / Q000032:analysis* / Q000138:chemical synthesis; D000242:Cyclic AMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010710:Phosphates; D013237:Stereoisomerism
D001896:Boron Compounds; D007202:Indicators and Reagents; D010710:Phosphates; D000242:Cyclic AMP; C035638:thiophosphoric acid