Scavenger mechanism of methylglyoxal by metformin. A DFT study
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| 024 | 7 | 0 | |a 10.1007/s00214-015-1649-z |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00214-015-1649-z | ||
| 245 | 0 | 0 | |a Scavenger mechanism of methylglyoxal by metformin. A DFT study |h [Elektronische Daten] |c [Christian Solís-Calero, Joaquín Ortega-Castro, Juan Frau, Francisco Muñoz] |
| 520 | 3 | |a 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. | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a α-Dicarbonyl compound |2 nationallicence | |
| 690 | 7 | |a Methylglyoxal |2 nationallicence | |
| 690 | 7 | |a Metformin |2 nationallicence | |
| 690 | 7 | |a Triazepine derivatives |2 nationallicence | |
| 690 | 7 | |a Non-enzymatic glycation |2 nationallicence | |
| 690 | 7 | |a AGEs |2 nationallicence | |
| 690 | 7 | |a DFT calculations |2 nationallicence | |
| 700 | 1 | |a Solís-Calero |D Christian |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | |
| 700 | 1 | |a Ortega-Castro |D Joaquín |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | |
| 700 | 1 | |a Frau |D Juan |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | |
| 700 | 1 | |a Muñoz |D Francisco |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | |
| 773 | 0 | |t Theoretical Chemistry Accounts |d Springer Berlin Heidelberg |g 134/4(2015-04-01), 1-14 |x 1432-881X |q 134:4<1 |1 2015 |2 134 |o 214 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00214-015-1649-z |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00214-015-1649-z |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Solís-Calero |D Christian |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Ortega-Castro |D Joaquín |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Frau |D Juan |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Muñoz |D Francisco |u Departament de Química, Institut d'Investigació en Ciències de la Salut (IUNICS), Universitat de les Illes Balears, 07122, Palma de Mallorca, Spain |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Theoretical Chemistry Accounts |d Springer Berlin Heidelberg |g 134/4(2015-04-01), 1-14 |x 1432-881X |q 134:4<1 |1 2015 |2 134 |o 214 | ||