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Nucleic Acids Research, 1974, Vol. 1, No. 12 1783-1799
© 1974

Articles

Seven-membered cyclic phosphate: synthesis and properties of S-cycloadenosine 2' 5'-cyclic phosphate and cordycepin 2', 5'-cyclic phosphate. Studies of nucleosides and nucleotides. LXIV'l). Purine cyclonucleosides 25.

Morio Ikehara and Junichi Yano

Faculty of Pharmaceutical Sciences, Osaka University Osaka, Japan

Received November 5, 1974. 8,3'-Anhydro-8-mercapto-9-ß-D-xylofuranosyladenine (8,3'-S-cycloadenosine) was phosphorylated with cyanoethyl phosphate and DCC to 5'-phosphate. After 6-amino group was benzoylated, the monophosphate was treated with DCC to give a cyclic phosphate (II). The structure of compound II was elucidated as 8,3'-S-cycloadenosine 2',5'-cyclic phosphate by UV, NMR and CD spectra, as well as enzymatic hydrolyses. When compound II was desulfurized with Raney nickel, cordycepin 2',5'-cyclic phosphate (III) was obtained. Although compound III could be obtained from cordycepin 5'-phosphate with DCC, the yield was extremely low.


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