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Issue 5, 2013
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Conformational properties of peptides incorporating a fluorinated pseudoproline residue

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Abstract

We have recently reported the synthesis of enantiomerically pure CF3-oxazolidine pseudoprolines (CF3-ΨPro). Complete NMR studies, together with DFT calculations, have highlighted the marked stereoelectronic effects of the CF3 group on these new proline surrogates. In this paper, we describe for the first time the conformational features of dipeptides incorporating one CF3-ΨPro residue. Extensive NMR analyses have been carried out in solution and revealed the presence of a stable type-VI β-turn in a pseudotetrapeptide sequence.

Graphical abstract: Conformational properties of peptides incorporating a fluorinated pseudoproline residue

  • This article is part of the themed collection: Prolines
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Supplementary files

Article information


Submitted
26 Nov 2012
Accepted
22 Jan 2013
First published
23 Jan 2013

New J. Chem., 2013,37, 1336-1342
Article type
Paper

Conformational properties of peptides incorporating a fluorinated pseudoproline residue

G. Chaume, D. Feytens, G. Chassaing, S. Lavielle, T. Brigaud and E. Miclet, New J. Chem., 2013, 37, 1336
DOI: 10.1039/C3NJ41084F

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