Theoretical study of the hydrolysis mechanism of β-lactam antibiotics catalysed by a Zn(II) dinuclear biomimetic organometallic complex
Journal
Molecular Physics
ISSN
0026-8976
1362-3028
Publisher
Taylor and Francis Group
Date Issued
2024
Author(s)
Zurita, Juan E.
Mora, José R.
Barigye, Stephen J.
Espinoza-Montero, Patricio J.
Type
text::journal::journal article
Abstract
The degradation and metabolism of antibiotics have attracted the scientific community's attention due to the environmental problems caused by the inappropriate use and disposal of these drugs. Therefore, it is crucial to understand the reaction mechanism involved in the degradation of these compounds. We studied the hydrolysis of nitrocefin and benzylpenicillin, two β-lactam ring antibiotics, mediated by an enzymatic mimetic Zn organometallic compound, using DFT methods. The electronic effects of functional groups adjacent to the β-lactam ring were analysed and good agreement between experimental and theoretical results was found. The reaction involves the nucleophilic attack of the bridging hydroxide group on the Zn atoms towards the β-lactam ring. A stepwise mechanism was found to agree with the experimental results. Chemical hardness profiles were affected by the solvent and reaction synchronicity. Geometric rearrangements dominated the activation barrier, and both antibiotics exhibited late transition states. ©
Taylor and Francis Group.
Taylor and Francis Group.
License
Acceso Restringido
How to cite
Zurita, J. E., Mora, J. R., Martinez-Rios, F., Barigye, S. J., & Espinoza-Montero, P. J. (2024). Theoretical study of the hydrolysis mechanism of β -lactam antibiotics catalysed by a Zn(II) dinuclear biomimetic organometallic complex. In Molecular Physics. Informa UK Limited. https://doi.org/10.1080/00268976.2024.2356752