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5-Iodo-2'-deoxyuridine 5'-Triphosphate, an Allosteric Inhibitor of Deoxycytidylate Deaminase

From the ¹ From the Department of Pharmacology, Yale University School of Medicine, New Haven, Connecticut 06510

5-Iodo-2'-deoxyuridine 5'-triphosphate (dIUTP) was synthesized in 30% yield from 5-iodo-2'-deoxycytidylate; and the allosteric nature of the inhibition by dIUTP of deoxycytidylate deaminase, derived from Ehrlich ascites carcinoma and L5178Y murine lymphoblastic cells, was compared to that produced by dTTP. The inhibition produced by the halogenated triphosphate derivative was found to be qualitatively similar to deoxythymidine triphosphate over a range of pH, temperature, and substrate concentrations; however, 5-iodo-2'-deoxyuridine 5'-triphosphate was quantitatively more inhibitory. A reversible competitive relationship was observed between the activator effect of deoxycytidine triphosphate and the inhibitory effect of 5-iodo-2'-deoxyuridine triphosphate when the concentration of the substrate, deoxycytidylate, was not rate-limiting. At low substrate concentrations the reaction velocity of deoxycytidylate deaminase was greatest at about 25°, and the rate of deamination decreased with deviation from this temperature in either direction.

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