title: Efficient syntheses of [2-(15)N]guanosine and 2'-deoxy[2-(15)N]guanosine derivatives.
abstract: Nucleophilic substitution of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine, prepared from guanosine, with N-tert-butyldimethylsilyl[(15)N]-phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[(15)N]phthalimidopurine derivative. Treatment of this with sodium 2-cyanoethoxide yielded the [2-(15)N]guanosine derivative. The 2'-deoxy[2-(15)N]guanosine derivative was also efficiently synthesized through a similar procedure.
authors.affiliation: Laboratory of Pharmaceutical Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Kazuo
authors.initials: K
authors.lastname: Kamaike
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Kayama
authors.forename: Mitsuhisa
authors.initials: M
authors.lastname: Isobe
authors.forename: Etsuko
authors.initials: E
authors.lastname: Kawashima
mesh_terms: D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009587:Nitrogen Isotopes
chemical_list: D009587:Nitrogen Isotopes; D003849:Deoxyguanosine