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Nucleic Acids Research, 1985, Vol. 13, No. 7 2451-2456
© 1985

Articles

Competition between the hydrolysis and deamination of cytidine and its 5-substituted derivatives in aqueous acid1

Harri Lönnberg and Rainer Käppi

Department of Chemistry and Biochemistry, University of Turku SF-2O5OO Turku, Finland

Received February 22, 1985. Accepted March 5, 1985.

The monocations of a few 5-substituted cytidines have been shown to undergo competitive deamination to the corresponding uridines and hydrolysis to 5-substituted cytosines and D-ribose. The first-order rate constants measured at different temperatures indicate that the proportion of the hydrolysis is considerably increased with the increasing temperature. Electron-withdrawal by a polar substituent at C5 appears to facilitate the hydrolysis to a larger extent than the deamination. The ionic strength has practically no influence on the rate of either reaction.


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