Studies on Synthetic Nucleotides

Part III. The Synthesis of 3-β-D-Ribofuranosyladenine 5'-Phosphate (The Synthesis and the Structure of 3-β-D-Ribofuranosyladenine 5'-Phosphate)

Abstract

A direct synthetic method of adenine nucleotides has been described. Treatment of adenine with 2, 3-di-O-benzoyl-5-diphenylphosphoryl-D-ribofuranosyl bromide in acetonitrile at 40°C, followed by removal of the protecting groups gave AMP and 3-iso-AMP. The structure and configuration in glycosidic center of the latter was established by UV and NMR spectral studies. Furthermore, treatment of 3-iso-AMP with 5'-nucleotidase gave the nucleoside, which is identical with 3-isoadenosine in its physical properties.