Synthesis of Nucleotides from 8,2′-Thioanhydropurine Nucleosides

Abstract

The 5′-mono and diphosphates of the common 8,2′-thioanhydropurine nucleosides have been prepared and studied with 5′-nucleotidase. alkaline phosphatase, and adenylate kinase. Procedures for the preparation of protected anhydronucleosides and their incorporation into dianhydronucleoside monophosphates have been developed. These nucleotides have been found to be completely resistant to spleen and snake venom phosphodiesterases but are readily converted with Raney nickel into the natural 2′-deoxy-nucleotides.

Synthesis of Nucleotides from O2,2′-Cyclouridine

“…There have also been two major reports on the incorporation of 8,2'-thioanhydropurine nucleosides into dinucleoside monophosphate units (20,21).…”

“…Of course there is a significant change in electronic and H-bonding characteristics of 15 as compared to 3. Further it has been observed that the cyclopurine nucleotides are not substrates for either snake venom or spleen phosphodiesterases (20). In the cyclopurines the base is constrained in a near anti conformation.…”