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Main Title: gamma-(S)-Trifluoromethyl proline: evaluation as a structural substitute of proline for solid state F-19-NMR peptide studies
Author(s): Kubyshkin, Vladimir
Afonin, Sergii
Kara, Sezgin
Budisa, Nediljko
Mykhailiuk, Pavel K.
Ulrich, Anne S.
Type: Article
Language Code: en
Abstract: gamma-(4S)-Trifluoromethyl proline was synthesised according to a modified literature protocol with improved yield on a multigram scale. Conformational properties of the amide bond formed by the amino acid were characterised using N-acetyl methyl ester model. The amide populations (s-trans vs. s-cis) and thermodynamic parameters of the isomerization were found to be similar to the corresponding values for intact proline. Therefore, the.-trifluoromethyl proline was suggested as a structurally low-disturbing proline substitution in peptides for their structural studies by F-19-NMR. Indeed, the exchange of native proline for gamma-trifluoromethyl proline in the peptide antibiotic gramicidin S was shown to preserve the overall amphipathic peptide structure. The utility of the amino acid as a selective F-19-NMR label was demonstrated by observing the re-alignment of the labelled gramicidin S in oriented lipid bilayers.
Issue Date: 2015
Date Available: 25-Oct-2017
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Journal Title: Organic & biomolecular chemistry : OBC
Publisher: Royal Society of Chemistry
Publisher Place: Cambridge
Volume: 13
Issue: 11
Publisher DOI: 10.1039/c5ob00034c
Page Start: 3171
Page End: 3181
EISSN: 1477-0539
ISSN: 1477-0520
Appears in Collections:FG Biokatalyse » Publications

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