Regioselective 1-alkylation of 2'-deoxyguanosine.
A method has been found for the regioselective alkylation of the nitrogen at the 1-position of 2'-deoxyguanosine. This consists in the reaction, in tetrahydrofuran solution, of a fully protected form of dG, namely the 3'5'-O-bis(tert-butyldimethylsilyl)-N2-dimethylaminomethylene derivative, with an alkyl halide in the presence of cesium carbonate. The yields of these previously unavailable derivatives of 2'-deoxyguanosine range from good to excellent. Confirmation of the structure of these substances comes from a comparison of their spectroscopic properties with those of the known 1-methyl homologue. In particular, the UV spectra of these new derivatives and the known 1-methyl homologue are essentially identical.
Huang
Yanhe
Y
Department of Pharmacological Sciences, State University of New York at Stony Brook, 11794-3400, USA.
Johnson
Francis
F
D000478:Alkylation; D003849:Deoxyguanosine / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet
D005663:Furans; D006842:Hydrocarbons, Brominated; C402368:N(7)-aminoguanosine; D006151:Guanosine; C018674:tetrahydrofuran; D003849:Deoxyguanosine