Abstract
Several glycating carbonyl compounds have been studied by resorting to the latest Minnesota family of density functional with the objective of determinating their molecular properties. In particular, the chemical reactivity descriptors that arise from conceptual density functional theory and chemical reactivity theory have been calculated through a DeltaSCF protocol. The validity of the KID (Koopmans’ in DFT) procedure has been checked by comparing the reactivity descriptors obtained from the values of the HOMO and LUMO with those calculated through vertical energy values. The reactivity sites have been determined by means of the calculation of the Fukui function indices, the condensed dual descriptor Delta {f}(mathbf {r}) and the electrophilic and nucleophilic Parr functions. The glycating power of the studied compounds have been compared with the same property for simple carbohydrates.Graphical abstractSeveral glycating carbonyl compounds have been studied by resorting to the latest Minnesota family of density functional with the objective of determinating their molecular properties, the chemical reactivity descriptors and the validity of the KID (Koopmans’ in DFT) procedure
Highlights
It is already well known that several diseases like diabetes, Alzheimer and Parkinson are related to the formation of the so called advanced glycation endproducts (AGEs)
The HOMO and LUMO orbital energies, ionization potentials I and electron affinities A, and global electronegativity χ, total hardness η, global electrophilicity ω, electrodonating power, (ω−), electroaccepting power (ω+), and net electrophilicity ω± of the studied glycating carbonyl compounds calculated with the eight density functionals and the Def2TZVP basis set using water as as solvent simulated with the SMD parametrization of the IEF-PCM model are presented in Additional file 1: Tables S1A–S8A
It should be remembered that only the vertical energy differences must be included instead of the adiabatic ones, because the Conceptual density functional theory (DFT) descriptors have been defined at a constant external potential v(r)
Summary
It is already well known that several diseases like diabetes, Alzheimer and Parkinson are related to the formation of the so called advanced glycation endproducts (AGEs). These toxic molecules are the result of a chain of reactions that is initiated by a nucleophilic addition between a reducing carbonyl compound and the amino groups of amino acids, peptides, and proteins. This is a nonenzymatic reaction (nonenzymatic glycation or Maillard reaction) that leads to the formation of a freely reversible Schiff base. The glycating power, that is, the abilty of different molecules with reducing carbonyl groups to interact with the amino
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