Abstract

The observed rates of enzyme-catalyzed abstraction of a proton from a carbon adjacent to a carbonyl/carboxylic acid group (α-proton of a carbon acid) require that the pKa of the a-proton be decreased such that it is equal to (±2-3 pK a units) or las than that of the protonated active site basic catalyst. This can be accomplished by concerted general acid-general base catalysis: Gerlt, J. A.; Kozarich, J. W.; Kenyon, G. L.; Gassman, P. G. J. Am. Chem. Soc. 1991, 113, 9667

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