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Towards a detailed description of pyridoxamine tautomeric species

Show simple item record Adrover Estelrich, Miguel Caldés Melis, Catalina Vilanova Canet, Bartolomé Frau Munar, Juan Donoso Pardo, Josefa Laurentina Muñoz Izquierdo, Francisco 2018-11-08T11:37:47Z
dc.description.abstract [eng] 3-Hydroxypyridine (3-HPY) and pyridoxamine (PM), one of the most relevant biological and biomedical vitamin B6 derivatives, are characterized to possess several ionic groups. This allows a complex tautomeric and ionic equilibria network formation that makes these systems difficult to characterize. Little is actually known about the physico-chemical descriptors of the minor tautomers which are essential for the biological and biomedical activity of PM. To characterize them, we have studied theoretically the ionic and tautomeric forms of 3-HPY and PM. Geometry, charges, molecular electrostatic potential maps and free energy values have been computed by using the PCM-MP2/6-311++G(d,p) theoretical level, whereas excitation energies and 13C chemical shifts have been computed on the optimized geometries at the PCM-B3LYP/6-311++G(d,p) level. Theoretical 13C chemical shifts and excitation energies have been validated experimentally. The individual protonation effect of the phenol group and pyridinic nitrogen as well as their combined effect on the depicted indicators is discussed. The provided results represent a further step in understanding the tautomeric equilibria in PM and enhance the characterization of the minor but essential tautomers. It also constitutes a plausible model to apply in the study of negligible tautomers in different systems.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a:
dc.relation.ispartof New Journal of Chemistry, 2012, vol. 36, p. 1571-1761
dc.rights (c) Adrover Estelrich, Miguel et al., 2012
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Towards a detailed description of pyridoxamine tautomeric species
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion 2018-11-08T11:37:48Z info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords físico-química
dc.subject.keywords Cálculos teóricos
dc.subject.keywords isodesmic reaction
dc.subject.keywords pKa calculations
dc.subject.keywords Chemical Kinetics
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess

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