A comparative study of the chemical reactivity of pyridoxamine, Ac-Phe-Lys and Ac-Cys with various glycationg carbonyl compounds.

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dc.contributor.author Adrover Estelrich, Miguel
dc.contributor.author Vilanova Canet, Bartolomé
dc.contributor.author Muñoz Izquierdo, Francisco
dc.contributor.author Donoso Pardo, Josefa Laurentina
dc.contributor.author Frau Munar, Juan
dc.date.accessioned 2018-10-22T11:38:00Z
dc.identifier.uri http://hdl.handle.net/11201/148205
dc.description.abstract [eng] Pyridoxamine (PM) has long been known to inhibit protein glycation via various mechanisms of action. One such mechanism involves the scavenging of carbonyl compounds with glycating ability. Despite the abundant literature on this topic, few quantitative kinetic studies on the processes involved have been reported. In this work, we conducted a comparative kinetic study under physiological pH and temperature conditions of the reactions of PM, Ac-Phe-Lys and Ac-Cys with various glycating carbonyl compounds (viz. aldehydes, α-oxoaldehydes and ketones). The microscopic formation rate constants for Schiff bases of PM and various carbonyl compounds, k 1, are of the same order of magnitude as those for the Schiff bases of Ac-Phe-Lys. However, because PM exhibits a higher proportion of reactive form at physiological pH, its observed second-order rate constant is ca. five times greater than that for Ac-Phe-Lys. That could explain PM ability to compete with amino residues in protein glycation. On the other hand, the observed formation rate constant for thiohemiacetals is four orders of magnitude greater than the formation constants for the Schiff bases of PM, which excludes PM as a competitive inhibitor of Cys residues in protein glycation.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1007/s00726-008-0098-6
dc.relation.ispartof Amino Acids, 2009, vol. 36, p. 437-448
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title A comparative study of the chemical reactivity of pyridoxamine, Ac-Phe-Lys and Ac-Cys with various glycationg carbonyl compounds.
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-22T11:38:00Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords Pyridoxamine (PM)
dc.subject.keywords Cinética química
dc.subject.keywords HPLC
dc.subject.keywords RMN
dc.subject.keywords Amino acids
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1007/s00726-008-0098-6

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