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Ministerio de EconomÃa y Competitividad (Espanya) | |
Cussó Forest, Olaf
Giuliano, Michael W. Ribas Salamaña, Xavi Miller, Scott J. Costas Salgueiro, Miquel |
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Supramolecular systems resulting from the combination of peptides and a chiral iron coordination complex catalyze asymmetric epoxidation with aqueous hydrogen peroxide, providing good to excellent yields and high enantioselectivities in short reaction times. The peptide is shown to play a dual role; the terminal carboxylic acid assists the iron center in the efficient H 2 O 2 activation step, while its β-turn structure is crucial to induce high enantioselectivity in the oxygen delivering step. The high level of stereoselection (84-92% ee) obtained by these supramolecular catalysts in the epoxidation of 1,1′-alkyl ortho-substituted styrenes, a notoriously challenging class of substrates for asymmetric catalysis, is not attainable with any other epoxidation methodology described so far. The current work, combining an iron center ligated to N and O based ligands, and a peptide scaffold that shapes the second coordination sphere, may be seen as a bott om up approach towards the design of artificial oxygenases MC acknowledge nancial support from MINECO of Spain and Fondo Europeo de Desarrollo Regional (CTQ2015-70795-P/ BQU), and the Catalan Department for Innovation, Universities and Enterprise (DIUE) of the Generalitat de Catalunya (2009SGR637). |
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http://hdl.handle.net/2072/299972 | |
eng | |
Royal Society of Chemistry (RSC) | |
Attribution-NonCommercial 3.0 Spain | |
http://creativecommons.org/licenses/by-nc/3.0/es/ | |
Oxigenases
Oxygenases Mecanismes de reacció (QuÃmica) Reaction mechanisms (Chemistry) |
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A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides | |
info:eu-repo/semantics/article | |
Recercat |