Efficient synthesis of [2-15N]guanosine and 2'-deoxy[2'-15N]guanosine derivatives using N-(tert-butyldimethylsilyl)[15N]phthalimide as a 15N-labeling reagent.
Nucleophilic aromatic substitution of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine with N-(tert-butyldimethylsilyl) [15N]phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[15N]phthalimidopurine derivative, which was subsequently converted to the [2-15N]guanosine derivative. The 2'-deoxy[2'-15N]guanosine derivative was also efficiently synthesized through a similar procedure.
Kamaike
Kazuo
K
School of Pharmarcy, Tokyo University of Pharmarcy and Life Sciences, Hachioji, Tokyo, Japan. kamaikek@ps.toyaku.ac.jp
Kayama
Yoshihiro
Y
Mitsuhisa
Isobe
I
Etsuko
Kawashima
K
D003849:Deoxyguanosine / Q000138:chemical synthesis* / Q000737:chemistry; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009587:Nitrogen Isotopes; D010797:Phthalimides / Q000737:chemistry*
C509131:N-(tert-butyldimethylsilyl)(15N)phthalimide; D009587:Nitrogen Isotopes; D010797:Phthalimides; D006151:Guanosine; D003849:Deoxyguanosine