The Kinetics and Mechanisms of Phosphoenolpyruvate Hydrolysis

S. J. Benkovic, K. J. Schray

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Abstract

The hydrolytic mechanisms of phosphoenolpyruvate and its reference compound ethyl phosphoenolpyruvate have been investigated. Rate constants for the protomeric species, activation energies, D2O and nonaqueous solvent effects, and methyl phosphate- inorganic phosphate product distribution in methanol- H2O solvent have led to the postulation of: (1) abnormally rapid phosphoenolpyruvate mono- and dianion and ethyl phosphoenolpyruvate monoanion hydrolysis via metaphosphate expulsion possibly involving a cyclic transition state, (2) unusual neutral species hydrolysis, (3) only small (3-40-fold) rate enhancement which was attributable to enol-ketone conversion energy, and (4) no demonstrable kinetically important role for the neighboring group of phosphoenolpyruvate.

Original languageEnglish (US)
Pages (from-to)4090-4096
Number of pages7
JournalBiochemistry
Volume7
Issue number11
DOIs
Publication statusPublished - Nov 1 1968

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All Science Journal Classification (ASJC) codes

  • Biochemistry

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