Molecular modeling annual

, Volume 3, Issue 10, pp 434–442

The Hydrolysis Mechanism of Formamide Revisited: Comparison Between ab initio, Semiempirical and DFT Results

Authors

  • Serge Antonczak
    • Laboratoire de Chimie Théorique, URA CNRS 510, Institut Nancéien de Chimie Moléculaire, Université Henri Poincaré, Nancy I. BP 239, F-54506 Vand_uvre-lès-Nancy Cedex, France; Tel. +33-3-8391-2527; Fax: +33-3-8391-2530 (ruiz@lctn.u-nancy.fr)
  • Manuel Ruiz-López
    • Laboratoire de Chimie Théorique, URA CNRS 510, Institut Nancéien de Chimie Moléculaire, Université Henri Poincaré, Nancy I. BP 239, F-54506 Vand_uvre-lès-Nancy Cedex, France; Tel. +33-3-8391-2527; Fax: +33-3-8391-2530 (ruiz@lctn.u-nancy.fr)
  • Jean-Louis Rivail
    • Laboratoire de Chimie Théorique, URA CNRS 510, Institut Nancéien de Chimie Moléculaire, Université Henri Poincaré, Nancy I. BP 239, F-54506 Vand_uvre-lès-Nancy Cedex, France; Tel. +33-3-8391-2527; Fax: +33-3-8391-2530 (ruiz@lctn.u-nancy.fr)
ORIGINAL PAPER

DOI: 10.1007/s008940050061

Cite this article as:
Antonczak, S., Ruiz-López, M. & Rivail, J. J Mol Med (1997) 3: 434. doi:10.1007/s008940050061

Abstract

The hydrolysis of amides is a model reaction to study peptide hydrolysis. This process has been previously considered in the literature at the ab initio level. In this work, we revisit different reaction mechanisms (water-assisted, non-assisted, neutral and acid-catalyzed) with various theoretical methods : semiempirical, ab initio and Density Functional. The ab initio calculations are carried out at a computational level which is substantially higher than in previous studies. We describe the structure of the transition states and discuss the influence of the catalyst. We also compute the activation free energies for these processes at the Density Functional Theory level. Comparison of the methods allows to outline the main trends of these theoretical approaches which may be useful to design new computational strategies for investigating biological reaction mechanisms through the use of combined Quantum Mechanics/Molecular Mechanics methods.

Keywords: AmidesHydrolysisReaction mechanismPeptidesTheoretical calculations

Copyright information

© Springer-Verlag Berlin Heidelberg 1997