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. 1). Purine cyclonucleosides 25.
8,3'-Anhydro-8-mercapto-9-beta-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.
D001593:Benzyl Compounds; D002854:Chromatography, Paper; D002942:Circular Dichroism; D000242:Cyclic AMP / Q000031:analogs & derivatives*; D003839:Deoxyadenosines / Q000031:analogs & derivatives*; D004590:Electrophoresis, Paper; D008968:Molecular Conformation; D009712:Nucleotides, Cyclic / Q000138:chemical synthesis*; D011687:Purines; D013056:Spectrophotometry, Ultraviolet; D013438:Sulfhydryl Compounds
D001593:Benzyl Compounds; D003839:Deoxyadenosines; D009712:Nucleotides, Cyclic; D011687:Purines; D013438:Sulfhydryl Compounds; D000242:Cyclic AMP