Alkylation of ribose in RNA reacted with ethylnitrosourea at neutrality

Abstract
Ribose O2 in TMV[tobacco mosaic virus]-RNA are ethylated by the carcinogen ethylnitrosourea in neutral aqueous solution (pH 6.1-7.3). 2''-O-Ethyladenosine, 2''-O-ethylguanosine, 2''-O-ethyluridine and 2''-O-ethylcytidine were identified as reaction products. The four 2''-O-ethyl nucleosides are found in approximately equal amounts and the total extent of ribose alkylation is about 15% of total ethylation. This finding, in conjunction with earlier results showing that all ring and phosphate O2 can be ethylated, signifies that every O2 in RNA or polyribonucleotides can react with ethylnitrosourea. The possible biological significance of ribose alkylation, resulting from chemical rather than enzymatic reaction, is discussed. The preparation of the new derivative 2''(3'')-O-ethylguanosine is described.

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