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Proposed mechanism for the reaction of FDTS. dUMP is activated by deprotonating N3 (1). The negative charge delocalizes onto O4 and O2, isolating electronically the enamine substructure (highlighted in yellow), enhancing its nucleophilicity for reaction with the methylene carbon of the flavin-iminium adduct proposed.8 Removal of the C5 proton of the bridged adduct by the phosphate of dUMP leads, ultimately, to production of dTMP and oxidized FAD.
