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Relative reactivities for monofunctional nitrogen mustard alkylation of nucleic acid components

1968; Elsevier BV; Volume: 166; Issue: 2 Linguagem: Inglês

10.1016/0005-2787(68)90222-0

1879-3002

Charles C. Price, G. Maurice Gaucher, Prasadarao Koneru, Rhchiro Shibakawa, John R. Sowa, Masao Yamaguchi,

RNA Interference and Gene Delivery

Quantitative studies of alkylation of nucleic acid bases have led to values for relative nucleophilicities of their reactive centers toward the diethylethylenimonium ion. The alkylation of native, double-helix DNA by diethylethylenimonium ion for 2 h at 40° and pH 7, followed by hydrolysis, dialysis and chromatography, showed only 7-alkylated guanine. After 48 h, considerable N6-alkylated adenine was also obtained. Since complete denaturation and extensive degradation of DNA occurred under the latter conditions, initially denatured DNA was alkylated for 2 h and found to give about equal amounts of both compounds. The alkylation of guanine in native DNA proceeded at a rate 50-fold greater and in denatured DNA at a rate 7-fold greater than in monomeric guanine ribosides and ribotides. While adenine units in native DNA are unreactive, in denatured DNA they react at a rate 5 times those in poly A.