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Nucleic Acids Research, 1979, Vol. 6, No. 6 2261-2273
© 1979

Articles

Fluoride ion catalyzed alkylation of nucleic acid derivatives using trialkyl phosphates, dialkyl sulfates and alkyl methanesulfonates

Kelvin K. Ogilvie, Serge L. Beaucage, Michael F. Gillen and Douglas W. Entwistle

Department of Chemistry, McGill University Montreal, Quebec, H3A 2K6, Canada

Received February 28, 1979. Trimethyl phosphate, dimethyl and diethyl sulfate and methyl and ethyl methanesulfonate all give high yields of alkylation on purifes and pyrimidines in the presence of tetrabutylammonium fluoride. Trimethyl phosphate produces near quantitative yields of diesters of nucleic acids but gives virtually no triester formation. The alkyl sulfates produce very high yields of triesters of nucleic acids including cyclic phosphates while thealkyl methanesulfonates are intermediate in reactivity. It was observed that in the absence of fluoride ion the dialkylesulfates gave reasonable yields of thymidine monosulfates.


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