Issue 5, 2013
From the journal:

New Journal of Chemistry

Conformational properties of peptides incorporating a fluorinated pseudoproline residue†

Grégory Chaume,a   Debby Feytens,bc   Gérard Chassaing,b   Solange Lavielle,b   Thierry Brigauda  and  Emeric Miclet*b  

* Corresponding authors

a Laboratoire SOSCO, Université de Cergy-Pontoise, EA 4505, 5 mail Gay Lussac, 95000 Cergy-Pontoise, France

b Laboratoire des BioMolécules, UMR 7203, Ecole Normale Superieure, UPMC Paris 06, 4, Place Jussieu, 75005 Paris, France
E-mail: emeric.miclet@upmc.fr
Fax: +33 1 44 27 71 50
Tel: +33 1 44 27 31 15

c Organic Chemistry Department, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium

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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Article information

DOI
https://doi.org/10.1039/C3NJ41084F
Article type
Paper
Submitted
26 Nov 2012
Accepted
22 Jan 2013
First published
23 Jan 2013

New J. Chem., 2013,37, 1336-1342

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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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