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Formation of Schiff bases of O-phosphorylethanolamine and O-phospho-D,L-serine with pyridoxal 5'-phosphate. Experimental and theoretical studies

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dc.contributor.author Vilanova Canet, Bartolomé
dc.contributor.author Gallardo, Jessica M.
dc.contributor.author Caldés Melis, Catalina
dc.contributor.author Adrover Estelrich, Miguel
dc.contributor.author Ortega-Castro, Joaquín
dc.contributor.author Muñoz Izquierdo, Francisco
dc.contributor.author Donoso Pardo, Josefa Laurentina
dc.date.accessioned 2018-10-11T10:59:59Z
dc.identifier.uri http://hdl.handle.net/11201/148032
dc.description.abstract [eng] Pyridoxal 5′-phosphate (PLP) is a B6 vitamer acting as an enzyme cofactor in various reactions of aminoacid metabolism and inhibiting glycation of biomolecules. Nonenzymatic glycation of aminophospholipids alters the stability of lipid bilayers and cell function as a result. Similarly to protein glycation, aminophospholipid glycation initially involves the formation of a Schiff base. In this work, we studied the formation of Schiff bases between PLP and two compounds mimicking the polar head of natural aminophospholipids, namely: O-phosphorylethanolamine and O-phospho-d,l-serine. Based on the results, the pH-dependence of the microscopic constants of the two PLP<br>aminophosphate systems studied is identical with that for PLP<br>aminoacid systems. However, the rate and equilibrium formation constants for the Schiff bases of the aminophosphates are low relative to those for the aminoacids. A theoretical study by density functional theory of the formation mechanism for the Schiff bases of PLP with the two aminophospholipid analogues confirmed that the activation energy of formation of the Schiff bases is greater with aminophosphates; on the other hand, that of hydrolysis is essentially similar with aminoacids and aminophosphates.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1021/jp2116033
dc.relation.ispartof Journal of Physical Chemistry A, 2012, vol. 116, num. 8, p. 1897-1905
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Formation of Schiff bases of O-phosphorylethanolamine and O-phospho-D,L-serine with pyridoxal 5'-phosphate. Experimental and theoretical studies
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-11T11:00:00Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords ESPECTROSCOPIA uv-vIS
dc.subject.keywords Cinética química
dc.subject.keywords Schiff bases
dc.subject.keywords DFT calculations
dc.subject.keywords PLP
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1021/jp2116033


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