Ilie, AdrianaLonsdale, RichardReetz, Manfred T.Agudo Torres, RubénUniversidad San Pablo-CEU. Departamento de Ciencias Farmacéuticas y de la SaludGrupo: Parasitología e Inmunología molecular con aplicación biotecnológica, diagnóstica y terapéutica (PARINM)2024-05-102024-05-102015-03-21A 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).0040-4039http://hdl.handle.net/10637/15770The 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.enrestricted accessBiocatalysisOxidationDiastereoselectivityArtículo10.1016/j.tetlet.2015.03.076https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es