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Topological control in radical reactions of cholesterol in model dyads

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Topological control in radical reactions of cholesterol in model dyads

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dc.contributor.author Neshchadin, Dmytro es_ES
dc.contributor.author Palumbo, Fabrizio es_ES
dc.contributor.author Sinicropi, M. Stefania es_ES
dc.contributor.author Andreu Ros, María Inmaculada es_ES
dc.contributor.author Gescheidt, Georg es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2016-10-04T11:01:28Z
dc.date.available 2016-10-04T11:01:28Z
dc.date.issued 2013
dc.identifier.issn 2041-6520
dc.identifier.uri http://hdl.handle.net/10251/71110
dc.description.abstract Cholesterol is one of the most important building blocks of cell membranes. It is also one of the main targets for oxidation via Type I hydrogen abstraction (HA), which leads to a variety of physiological consequences in the human body. To provide a deeper understanding of the oxidation mechanism, steady-state H-1 CIDNP, steady-state and laser-flash photolysis in combination with quantum mechanical calculations were applied to study HA in three model systems. The experiments involved photoinduced reactions in a cholesterol-benzophenone mixture and two derivatives, in which aminocholestene and benzophenone are covalently coupled yielding a dyad. It has been found, that a specific orientation of the benzophenone moiety toward the allylic hydrogens of cholesterol/aminocholestene is crucial for the efficient HA. Such a confined topology may play an important role for the particular oxidation of cholesterol in cell membranes. es_ES
dc.description.sponsorship Financial support from the MICINN (Grants CTQ2009-13699 and CTQ2010-14882), from the Generalitat Valenciana (Grisolia fellowship for F. P.) from the Carlos III Institute of Health (Grant RIRAAF, RETICS program and Miguel Servet Contract CP11/00154 for I. A.) and TU Graz is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Chemical Science es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject LASER FLASH-PHOTOLYSIS es_ES
dc.subject TIME-RESOLVED CIDNP es_ES
dc.subject HYDROGEN ABSTRACTION es_ES
dc.subject LIPID-PEROXIDATION es_ES
dc.subject BENZOPHENONE es_ES
dc.subject MECHANISMS es_ES
dc.subject CHEMISTRY es_ES
dc.subject MEMBRANES es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Topological control in radical reactions of cholesterol in model dyads es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c3sc22109a
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CTQ2010-14882/ES/DIADAS FOTOACTIVAS COMO SONDAS PARA LA GENERACION DE ESPECIES TRANSITORIAS EN SISTEMAS MICROHETEROGENEOS DE TIPO BIOMIMETICO/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CP11%2F00154/ES/CP11%2F00154/ es_ES
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Neshchadin, D.; Palumbo, F.; Sinicropi, MS.; Andreu Ros, MI.; Gescheidt, G.; Miranda Alonso, MÁ. (2013). Topological control in radical reactions of cholesterol in model dyads. Chemical Science. 4(4):1608-1614. https://doi.org/10.1039/c3sc22109a es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c3sc22109a es_ES
dc.description.upvformatpinicio 1608 es_ES
dc.description.upvformatpfin 1614 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 4 es_ES
dc.description.issue 4 es_ES
dc.relation.senia 237636 es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Instituto de Salud Carlos III es_ES
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