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Free energy profiles for the enzyme-catalyzed deuterium exchange reactions of the phosphodianion forms of UMP and F-UMP (SD2−) through the respective C-6 vinyl carbanion intermediates. These profiles were constructed according to the mechanism shown in Scheme 9, with the observed 3400-fold faster deuterium exchange into enzyme-bound F-UMP than UMP and a barrier to rotation of the terminal CH2-NL3+ bond of the side chain of Lys-93 of 8 kcal/mol (see text).
