Nucleotides. III. Syntheses of deazaadenosine 3',5'-cyclic phosphates and related nucleotides of biological interest.

Abstract

1-Deaza-(I) and 3-deazaadenosine 3', 5'-cyclic phosphate (II) (analogs of adenosine 3', 5'-cyclic phosphate) were synthesized from N6-acetyl-1-deazaadenosine (III) and 3-deazaadenosine (VI), respectively. In addition, a number of 1-and 3-deazaadenosine phosphates including 1-(XII) and 3-deazaadenosine 2', 3'-cyclic phosphate (XIII) were also prepared. Both VII and XIII were found to be hydrolyzed to the corresponding nucleoside 3'-phosphate by ribonuclease M. Both 1-deaza-(V) and 3-deazaadenosine 5'-phosphate (XI) were hydrolyzed by snake venom 5'-nucleotidase to the respective deazaadenosine and inorganic phosphate; the latter, however, was found to be hydrolyzed with much reduced rate.