Efficient syntheses of 5'-deoxy-5'-fluoroguanosine and -inosine.
Substitution of oxygen with a weak hydrogen bond acceptor such as fluorine provides a single-atom modification that can have grave effects on the chemical and medicinal properties of nucleoside analogues. To that end, we present a simple and high-yielding method for the novel synthesis of 5'-deoxy-5'-fluoroguanosine and 5'-deoxy-5'-fluoroinosine utilizing an intramolecular electron-withdrawing approach. The properties of the resulting modified nucleosides, as well as the halogenated intermediates, are notable for their similarity to nucleoside analogues used in the treatment of cancer, as well as enzyme inhibitors designed to target parasitic protozoa.
Spitale
Robert C
RC
Department of Biochemistry & Biophysics, University of Rochester Medical Center, 601 Elmwood Avenue, Box 712, Rochester, New York 14642, USA.
Heller
Moriah G
MG
Pelly
Amanda J
AJ
Wedekind
Joseph E
JE
D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007288:Inosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009690:Nucleic Acid Conformation; D013237:Stereoisomerism
C525408:5'-deoxy-5'-fluoroguanosine; C525409:5'-deoxy-5'-fluoroinosine; D006151:Guanosine; D007288:Inosine