13C chemical shifts and Jc,h coupling constants are reported for 17 5-substituted uracils. Overall, the chemical shifts at C-5 and C-6 of the 5-substituted uracils exhibit no obvious correlation with substituent electronegativity. Instead, when the 5-substituted uracils are considered as trisubstituted ethylenes, the chemical shift data are shown to be rationalized in terms of the ability of the C-5 substituent to behave as a mesomeric acceptor or donor. It is also demonstrated that the correlation of the chemical shifts at C-6 can be used to identify two categories of 5-substituted uracils whose parent deoxynucleotide derivatives are inhibitors of the enzyme, thymidylate synthetase. It is suggested that 13C nmr spectroscopy is a potentially useful tool for predicting the effectiveness of certain modified substrates as enzymatic inhibitors.Uracil and certain of its 5-substituted analogs are involved in a number of biochemically significant roles (i.e., constituents of RNA and DNA) in all(1) Presented in part at the 162nd National Meeting of the American
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