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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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Article information


Submitted
09 Jan 2017
Accepted
03 Mar 2017
First published
03 Mar 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 3660-3667
Article type
Edge Article

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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