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Improved syntheses, based on Lewis acid-catalyzed nucleosidation, are described for the preparation of 5-alkyl-2'-deoxyuridines. These were converted to their 5'-phosphates with the use of wheat shoot phosphotransferase. The dUMP analogues, 5-ethyl-dUMP and 5-propyl-dUMP, were competitive vs dUMP inhibitors of thymidylate synthetase purified from mouse L1210, Ehrlich ascites and HeLa cells, the former being the stronger inhibitor. Both analogues were shown to bind cooperatively to each of the mouse tumour enzymes, two molecules of inhibitor interacting with a single enzyme molecule, as reflected by the parabolic character of the replots of the slope vs inhibitor concentrations. dTMP was a stronger inhibitor of the mouse tumour enzymes than its higher alkyl homologues.
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