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Reactivity of a Phospholipid Monolayer Model under Periodic Boundary Conditions. A DFT Study of the Schiff base formation between Phosphatidylethanomanine and Acetaldehyde

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dc.contributor.author Solís Calero, C.
dc.contributor.author Ortega Castro, Joaquín
dc.contributor.author Muñoz Izquierdo, Francisco
dc.date.accessioned 2018-11-19T11:39:13Z
dc.identifier.uri http://hdl.handle.net/11201/148537
dc.description.abstract [eng] A mechanism for the formation of the Schiff base between an acetaldehyde and an aminephospholipid monolayer model based on Dmol3/density functional theory calculations under periodic boundary conditions was constructed. This is the first time such a system has been modeled to examine its chemical reactivity at this computation level. Each unit cell contains two phospholipid molecules, one acetaldehyde molecule, and nine water molecules. One of the amine-phospholipid molecules in the cell possesses a neutral amino group that is used to model the nucleophilic attack on the carboxyl group of acetaldehyde, whereas the other has a charged amino group acting as a proton donor. The nine water molecules form a hydrogen bond network along the polar heads of the phospholipids that facilitates very fast proton conduction at the interface. Using periodic boundary conditions afforded proton transfer between different cells. The reaction takes place in two steps, namely, (1) formation of a carbinolamine and (2) its dehydration to the Schiff base. The carbinolamine is the primary reaction intermediate, and dehydration is the rate-determining step of the process, consistent with available experimental evidence for similar reactions. On the basis of the results, the cell membrane surface environment may boost phospholipid glycation via a neighboring catalyst effect.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1021/jp1088367
dc.relation.ispartof Journal of Physical Chemistry B, 2010, vol. 114, p. 15879-15885
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Reactivity of a Phospholipid Monolayer Model under Periodic Boundary Conditions. A DFT Study of the Schiff base formation between Phosphatidylethanomanine and Acetaldehyde
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-11-19T11:39:13Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords DFT
dc.subject.keywords Chemical Kinetics
dc.subject.keywords Cálculos teóricos
dc.subject.keywords lipid peroxidation
dc.subject.keywords físico-química
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1021/jp1088367


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