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Updated: Aug 13, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Regioselective 1-alkylation of 2'-deoxyguanosine
1Department of Pharmacological Sciences, State University of New York at Stony Brook, 11794-3400, USA.
Abstract:
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.
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