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Scavenger Mechanism of Methylglyoxal by Metformin. A DFT Study

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dc.contributor.author Solís-Calero, Christian
dc.contributor.author Ortega Castro, Joaquín
dc.contributor.author Frau Munar, Juan
dc.contributor.author Muñoz Izquierdo, Francisco
dc.date.accessioned 2018-10-11T11:26:25Z
dc.identifier.uri http://hdl.handle.net/11201/148034
dc.description.abstract [eng] 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<br>guanylhydrazone<br>acetylcarbinol adduct, (2) formation of a zwitterionic triazepine derivative by ring closure, (3) dehydration of this intermediate, (4) an imine<br>enamine tautomerism, (5) an enol<br>keto tautomerism. The first step was found as the rate-determining step for the reaction, having the reaction an overall activation energy value of 9.7 kcal mol−1.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1007/s00214-015-1649-z
dc.relation.ispartof Theoretical Chemistry Accounts, 2015, vol. 134, p. 48
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Scavenger Mechanism of Methylglyoxal by Metformin. A DFT Study
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-11T11:26:25Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords DFT calculations
dc.subject.keywords Metformine
dc.subject.keywords methylglyoxal
dc.subject.keywords AGEs
dc.subject.keywords Non-enzymatic glycation
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1007/s00214-015-1649-z


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