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Issue 25, 2014
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Proline N-oxides: modulators of the 3D conformation of linear peptides through “NO-turns”

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Abstract

Small peptides are essential mediators of numerous physiological processes. Consequently, there is huge interest in the de novo design of peptides with a predictable folding and related biological activity. In this study, we investigate the possibility of modulating the secondary structure of tetrapeptides through proline N-oxide moieties and N-methylation of the peptide backbone. A series of tetrapeptides were synthesised to investigate the combined effect of Pro N-oxide and N-methylation of the amide bond on the (n + 1) residue in terms of cis- and trans-isomerization, as well as how these modifications direct potential intramolecular hydrogen bonding interactions. The right combination of both these parameters led to a trans to cis-conformational interconversion and a change in the nature of the hydrogen bonding interactions, as demonstrated by NMR spectroscopic, molecular modeling analysis and thermal coefficient studies. Proline N-oxide residues were proposed to induce turns we named as NO-γ-turns and NO-β-turns based on their similarity to traditional γ- and β-turns.

Graphical abstract: Proline N-oxides: modulators of the 3D conformation of linear peptides through “NO-turns”

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Publication details

The article was received on 25 Feb 2014, accepted on 09 Apr 2014 and first published on 09 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00433G
Citation: Org. Biomol. Chem., 2014,12, 4479-4490
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    Proline N-oxides: modulators of the 3D conformation of linear peptides through “NO-turns”

    M. D. Farahani, B. Honarparvar, F. Albericio, G. E. M. Maguire, T. Govender, P. I. Arvidsson and H. G. Kruger, Org. Biomol. Chem., 2014, 12, 4479
    DOI: 10.1039/C4OB00433G

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