REDUCTION OF 5-URACILYLMETHYLENEPYRIDINIUM SALTS BY THIOLS. A MODEL OF THE REDUCTION STEP OF THE THYMIDYLATE SYNTHASE REACTION

Article abstract of DOI:10.1016/S0040-4020(01)87105-2

Reaction of 1-(5-uracilylmethylene)pyridinium salts with thiols leads to the formation of the corresponding thymine derivatives.This transformation of a uracil derivative to the corresponding thymine is explained on the basis of the formation of an exocyclicmethylene intermediate, analogous to that proposed in the thymidylate synthase reaction, followed by its reduction by additional thiol, presumably involving a radical mechanism.