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Mechanistic implications of substrate tautomerization. (A) A mechanistic scheme for the decarboxylation of S-keto 7-carboxy-K252c in a StaC-like enzyme, where the reaction is initiated by decarboxylation. (B) Hybridization of the C-7 carbon in the enol tautomer of 7-carboxy-K252c makes decarboxylation as the first step in the mechanism unlikely. (C) A mechanistic scheme for RebC in which oxidation precedes decarboxylation at the C-7 position.
