Abstract
Abstract 5-Fluoropropynyl-2′-deoxyuridine 5′-phosphate ( 3 ) was designed as a mechanism-based inactivator of thymidylate synthase (TS). The inhibitor was synthesized from 5-iodo-2′-deoxyuridine and propargyl alcohol by palladium-catalyzed coupling, followed by fluorination and selective phosphorylation. Incubation of TS with 3 , in the presence or absence of the CH 2 H 4 folate cofactor, caused rapid, irreversible inactivation of the enzyme.
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