Here, we report on a mechanistic investigation based on DFT calculations and kinetic measures aimed at determining the energetics related to the cysteine nucleophilic attack on nitrile-carrying compounds. Activation energies were found to correlate well with experimental kinetic measures of reactivity with cysteine in phosphate buffer. The agreement between computations and experiments points to this DFT-based approach as a tool for predicting both nitrile reactivity toward cysteines and the toxicity of nitriles as electrophile agents.
Predicting the reactivity of nitrile-carrying compounds with cysteine: a combined computational and experimental study / Berteotti, A; Vacondio, Federica; Lodola, Alessio; Bassi, M; Silva, Claudia; Mor, Marco; Cavalli, A.. - In: ACS MEDICINAL CHEMISTRY LETTERS. - ISSN 1948-5875. - 5:(2014), pp. 501-505. [10.1021/ml400489b]
Predicting the reactivity of nitrile-carrying compounds with cysteine: a combined computational and experimental study.
VACONDIO, Federica;LODOLA, Alessio;SILVA, Claudia;MOR, Marco;
2014-01-01
Abstract
Here, we report on a mechanistic investigation based on DFT calculations and kinetic measures aimed at determining the energetics related to the cysteine nucleophilic attack on nitrile-carrying compounds. Activation energies were found to correlate well with experimental kinetic measures of reactivity with cysteine in phosphate buffer. The agreement between computations and experiments points to this DFT-based approach as a tool for predicting both nitrile reactivity toward cysteines and the toxicity of nitriles as electrophile agents.File | Dimensione | Formato | |
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