Computational Study of n-Acetylglutamate Hydrolysis under Acidic and Basic Conditions

Abstract

Aims: To study N-acetylglutamate hydrolysis under acidic and basic conditions, using molecular modeling techniques.   Study Design: Hydrolysis of N-acetylglutamate was studied under acidic and basic conditions to establish the differences in chemical properties and conditions of favorability; this was performed using the Mulliken charges and the geometric parameters as descriptors, as well as proton affinity, Gibbs free energy, and equilibrium constants. Place and Duration of Study: Grupo de Investigación Max Planck, Facultad de Química y Farmacia, Universidad del Atlántico, between February 2014 and March 2015. Methodology: Structures of the hydrolysis reaction under acidic and basic conditions were optimized using molecular mechanics prior to calculating various molecular descriptors. The Hartree–Fock (HF) method was used with the 3-21G and 6-31G* basis sets. Some useful parameters for analyzing the reactions are proton affinity, Frontier Molecular Orbitals, Gibbs free energy, and equilibrium constants. Results: In general, reaction profiles demonstrated that the two reactions are favorable; however, in agreement with our preliminary equilibrium constant findings, a greater favorability for basic hydrolysis was shown. Conclusion: The calculated equilibrium constants are in agreement with the favorability of hydrolysis under basic conditions, which is consistent with the biochemical process.