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

Please use this identifier to cite or link to this item: http://hdl.handle.net/10637/15770

See/Open:
Catalyzed_Ilie_et_al_Tetrah_Letters_2015.PNG
13,68 kB
image/png

See/Open:
Catalyzed_Ilie_et_al_Tetrah_Letters_2015.pdf
Restricted Access
565,5 kB
Adobe PDF
Request a copy

Title:	A diastereoselective P450-catalyzed epoxidation reaction: anti versus syn reactivity
Authors :	Ilie, Adriana Lonsdale, Richard Agudo Torres, Rubén Reetz, Manfred T.
Keywords:	Biocatalysis; Oxidation; Diastereoselectivity
Publisher:	Elsevier
Citation:	A 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).
Abstract:	The 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.
URI:	http://hdl.handle.net/10637/15770
Rights :	http://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
ISSN:	0040-4039
Issue Date:	21-Mar-2015
Center :	Universidad San Pablo-CEU
Appears in Collections:	Facultad de Farmacia

Show full item record