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Issue 5, 2017
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A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides

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Abstract

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 H2O2 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 bottom up approach towards the design of artificial oxygenases.

Graphical abstract: A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides

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Publication details

The article was received on 09 Jan 2017, accepted on 03 Mar 2017 and first published on 03 Mar 2017


Article type: Edge Article
DOI: 10.1039/C7SC00099E
Citation: Chem. Sci., 2017,8, 3660-3667
  • Open access: Creative Commons BY-NC license
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    A bottom up approach towards artificial oxygenases by combining iron coordination complexes and peptides

    O. Cussó, M. W. Giuliano, X. Ribas, S. J. Miller and M. Costas, Chem. Sci., 2017, 8, 3660
    DOI: 10.1039/C7SC00099E

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