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DFT study of the mechanism of the reaction of aminoguanidine with methylglyoxal

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dc.contributor.author Solís Calero, Christian
dc.contributor.author Ortega Castro, Joaquín
dc.contributor.author Hernández Laguna, Alfonso
dc.contributor.author Muñoz Izquierdo, Francisco
dc.date.accessioned 2018-11-08T12:12:37Z
dc.identifier.uri http://hdl.handle.net/11201/148489
dc.description.abstract [eng] We have studied the mechanism of the reaction between aminoguanidine (AG) and methylglyoxal (MG) by carrying out Dmol3/DFT calculations, obtaining intermediates, transition-state structures, and free-energy profiles for all of the elementary steps of the reaction. Designed models included explicit water solvent, which forms hydrogen-bond networks around the reactants and intermediate molecules, facilitating intramolecular proton transfer in some steps of the reaction mechanism. The reaction take place in four steps, namely: (1) formation of a guanylhydrazone<br>acetylcarbinol adduct by condensation ofAG andMG; (2) dehydration of the adduct; (3) formation of an 1,2,4-triazine derivative by ring closure; and (4) dehydration with the formation of 5-methyl 3- amino-1,2,4-triazine as the final product. From a microkinetic point of view, the first dehydration step was found to be the rate-determining step for the reaction, with the reaction having an apparent activation energy of 12.65 kcal mol−1. Additionally, some analogous structures of intermediates and transition states for the reaction between AG and 2,3-dicarbonyl-phosphatidylethanolamine, a possible intermediate in Amadoriglycated phosphatidylethanolamine (Amadori-PE) autooxidation, were obtained to evaluate the reaction above a phosphatidylethanolamine (PE) surface. Our results are in agreement with experimental results obtaining by other authors, showing that AG is efficient at trapping dicarbonyl compounds such as methylglyoxal, and by extension these compounds joined to biomolecules such as PE in environments such as surfaces and their aqueous surroundings
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1007/s00894-014-2202-z
dc.relation.ispartof Journal of Molecular Modeling, 2014, vol. 20, num. 4, p. 2202
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title DFT study of the mechanism of the reaction of aminoguanidine with methylglyoxal
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-11-08T12:12:37Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords DFT
dc.subject.keywords aminoguanidine
dc.subject.keywords Theoretical study
dc.subject.keywords methylglyoxal
dc.subject.keywords AGE inhibitors
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1007/s00894-014-2202-z


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