A diastereoselective P450-catalyzed epoxidation reaction: anti versus syn reactivity

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dc.centroUniversidad San Pablo-CEU
dc.contributor.authorIlie, Adriana
dc.contributor.authorLonsdale, Richard
dc.contributor.authorReetz, Manfred T.
dc.contributor.authorAgudo Torres, Rubén
dc.contributor.otherUniversidad San Pablo-CEU. Departamento de Ciencias Farmacéuticas y de la Salud
dc.contributor.otherGrupo: Parasitología e Inmunología molecular con aplicación biotecnológica, diagnóstica y terapéutica (PARINM)
dc.date.accessioned2024-05-10T15:13:35Z
dc.date.available2024-05-10T15:13:35Z
dc.date.issued2015-03-21
dc.description.abstractThe achiral cyclohexene derivative dimethyl cis-1,2,3,6-tetrahydrophthalate has been subjected to oxidation catalyzed by cytochrome P450 monooxygenase P450-BM3, leading to diastereoselective epoxidation rather than oxidative hydroxylation. This reaction occurs with 94% diastereoselectivity in favor of the anti-epoxide, in contrast to m-CPBA which delivers unselectively a 70:30 mixture of anti/syn diastereomers. The experimental results are nicely explained on a molecular level by docking experiments and molecular dynamics computations.es_ES
dc.identifier.citationA diastereoselective P450-catalyzed epoxidation reaction: anti versus syn reactivity. Ilie A, Lonsdale R, Agudo R, Reetz MT. Tetrahedron Letters 56, 23, pp. 3435 - 3437 (2015).es_ES
dc.identifier.doi10.1016/j.tetlet.2015.03.076
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/10637/15770
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofTetrahedron Letters
dc.rightsrestricted access
dc.rights.cchttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
dc.subjectBiocatalysisen_EN
dc.subjectOxidationen_EN
dc.subjectDiastereoselectivityen_EN
dc.titleA diastereoselective P450-catalyzed epoxidation reaction: anti versus syn reactivityen_EN
dc.typeArtículo
dspace.entity.typePublicationes
relation.isAuthorOfPublication6c8d28e1-0f33-443a-a16b-508aef52ff02
relation.isAuthorOfPublication.latestForDiscovery6c8d28e1-0f33-443a-a16b-508aef52ff02

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