DFT Studies on Schiff Base Formation on Vitamin B6 analogues. Reaction between a pyridoxamine-analogue and carbonyl compounds

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dc.contributor.author Ortega-Castro, Joaquín
dc.contributor.author Adrover Estelrich, Miguel
dc.contributor.author Frau Munar, Juan
dc.contributor.author Salvà, A.
dc.contributor.author Donoso Pardo, Josefa Laurentina
dc.contributor.author Muñoz Izquierdo, Francisco
dc.date.accessioned 2018-10-22T12:45:37Z
dc.identifier.uri http://hdl.handle.net/11201/148206
dc.description.abstract [eng] A comprehensive theoretical study based on density functional theory calculations (B3LYP and M06−2X functionals) of the formation of Schiff bases of pyridoxamine analogues with two different aldehydes was conducted. The reaction mechanism was found to involve two steps, namely: (1) formation of a carbinolamine and (2) dehydration of the carbinolamine to give the final imine. Also, consistent with available experimental evidence, the carbinolamine dehydration was the rate-determining step of the process determined by means of M06−2X functional. Using an appropriate solvation method and reactant conformation ensures that all proton transfers involved will be intramolecular, which substantially reduces energy barriers and facilitates reaction in all cases. The formation of a Schiff base between pyridoxal 5-phosphate (PLP) and an amine or amino acid requires the contribution of an external water molecule in order to facilitate proton transfers. On the other hand, the formation of a Schiff base between pyridoxamine 5-phosphate (PMP) and a carbonyl compound requires no external aid since the spatial arrangement of the functional groups in PMP ensures that all proton transfers will be intramolecular.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1021/JP909156M
dc.relation.ispartof Journal of Physical Chemistry A, 2010, vol. 114, p. 4634-4640
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title DFT Studies on Schiff Base Formation on Vitamin B6 analogues. Reaction between a pyridoxamine-analogue and carbonyl compounds
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-22T12:45:37Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords Vitamin b6
dc.subject.keywords Chemical Kinetics
dc.subject.keywords Schiff bases
dc.subject.keywords Pyridoxamine (PM)
dc.subject.keywords correlación electrónica
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1021/JP909156M

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