Literature DB >> 24900869

Predicting the reactivity of nitrile-carrying compounds with cysteine: a combined computational and experimental study.

Anna Berteotti1, Federica Vacondio2, Alessio Lodola2, Michele Bassi2, Claudia Silva2, Marco Mor2, Andrea Cavalli3.   

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.

Entities:  

Keywords:  Cysteine; DFT; nitrile reactivity; nucleophilic attack

Year:  2014        PMID： 24900869      PMCID： PMC4027605          DOI： 10.1021/ml400489b

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  23 in total

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