caa a22 4500 605488037 CHVBK 20210128100453.0 cr unu---uuuuu 210128e20150401xx s 000 0 eng 10.1007/s00214-015-1649-z doi (NATIONALLICENCE)springer-10.1007/s00214-015-1649-z Scavenger mechanism of methylglyoxal by metformin. A DFT study [Elektronische Daten] [Christian Solís-Calero, Joaquín Ortega-Castro, Juan Frau, Francisco Muñoz] We have studied the mechanism of the reaction between the most stable and the most represented in literature tautomers of metformin and methylglyoxal by density functional theory calculations. Designed models included 16 explicit water solvent, which forms hydrogen bond networks around the reactants and intermediates molecules, facilitating intramolecular proton transfer in some steps of the reaction mechanism. The reaction takes place in five steps, namely: (1) formation of a dimethylguanide-guanylhydrazone-acetylcarbinol adduct, (2) formation of a zwitterionic triazepine derivative by ring closure, (3) dehydration of this intermediate, (4) an imine-enamine tautomerism, (5) an enol-keto tautomerism. The first step was found as the rate-determining step for the reaction, having the reaction an overall activation energy value of 9.7kcalmol−1. Springer-Verlag Berlin Heidelberg, 2015 α-Dicarbonyl compound nationallicence Methylglyoxal nationallicence Metformin nationallicence Triazepine derivatives nationallicence Non-enzymatic glycation nationallicence AGEs nationallicence DFT calculations nationallicence Solís-Calero Christian Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut Ortega-Castro Joaquín Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut Frau Juan Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut Muñoz Francisco Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut Theoretical Chemistry Accounts Springer Berlin Heidelberg 134/4(2015-04-01), 1-14 1432-881X 134:4<1 2015 134 214 https://doi.org/10.1007/s00214-015-1649-z text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00214-015-1649-z text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Solís-Calero Christian Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut NATIONALLICENCE 700 1- Ortega-Castro Joaquín Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut NATIONALLICENCE 700 1- Frau Juan Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut NATIONALLICENCE 700 1- Muñoz Francisco Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain aut NATIONALLICENCE 773 0- Theoretical Chemistry Accounts Springer Berlin Heidelberg 134/4(2015-04-01), 1-14 1432-881X 134:4<1 2015 134 214