Chemical and Pharmaceutical Bulletin p. 3410 - 3416 (1984)
Update date:2022-08-02
Topics:
Ueda
Usui
Shuto
Inoue
6,5'-Cyclo-5'-deoxyuridine, a fixed anti form of uridine, was synthetized by a radical cyclization of 5'-bromo(or iodo)-5'-deoxy-2',3'-O-isopropylidene-5-chloro(or bromo)-uridine and tri-n-butyltin hydride followed by dehydrohalogenation and deacetonation. The 5-bromo and 4-thio derivatives of the cyclouridine were also prepared and were converted to the 2',3'-cyclic phosphates. These nucleotides were hydrolyzed by pancreatic ribonuclease. The result showed that the enzyme recognizes the pyrimidine nucleotides in the anti form. 6,5'-Cyclo-5'-deoxycytidine was also synthesized by two routes.
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