Cleavage of the glycosidic linkage of pyrimidine ribonucleosides by the bisulfite-oxygen system.

When a solution containing 2 mM uridine, 20 mM sodium bisulfite, 0.1 mM MnCl(2), and 100 mM sodium phosphate buffer of pH 7.0 was incubated aerobically at 37 degrees or 0 degrees , partial cleavage of the glycosidic linkage of uridine took place. About 20% of the uridine was converted to uracil by the incubation for 4 hrs. Cytosine was produced from cytidine by similar treatment with bisulfite. These reactions were caused by free radicals generated by Mn(2+)-catalyzed autoxidation of bisulfite. Glycosidic bond cleavage by the bisulfite-oxygen system was not detected for adenosine, AMP, guanosine, GMP, thymidine, TMP, deoxyuridine, dCMP, dAMP, and dGMP. When poly(U) and poly(C) were treated with 20 mM sodium bisulfite in the same manner, chain fission of the polymer occurred as judged by the elution-pattern change in gel filtration through Sephadex columns. No change in the elution pattern was observed for bisulfite-treated poly(A), poly(U). poly(A) or tRNA.