gamma-(S)-Trifluoromethyl proline: evaluation as a structural substitute of proline for solid state F-19-NMR peptide studies
| dc.contributor.author | Kubyshkin, Vladimir | |
| dc.contributor.author | Afonin, Sergii | |
| dc.contributor.author | Kara, Sezgin | |
| dc.contributor.author | Budisa, Nediljko | |
| dc.contributor.author | Mykhailiuk, Pavel K. | |
| dc.contributor.author | Ulrich, Anne S. | |
| dc.date.accessioned | 2017-10-25T06:29:01Z | |
| dc.date.available | 2017-10-25T06:29:01Z | |
| dc.date.issued | 2015 | |
| dc.description.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. | en |
| dc.identifier.eissn | 1477-0539 | |
| dc.identifier.issn | 1477-0520 | |
| dc.identifier.pmid | 25703116 | |
| dc.identifier.uri | https://depositonce.tu-berlin.de/handle/11303/6972 | |
| dc.identifier.uri | http://dx.doi.org/10.14279/depositonce-6311 | |
| dc.language.iso | en | |
| dc.rights.uri | https://creativecommons.org/licenses/by/3.0/ | |
| dc.subject.ddc | 540 Chemie und zugeordnete Wissenschaften | de |
| dc.title | gamma-(S)-Trifluoromethyl proline: evaluation as a structural substitute of proline for solid state F-19-NMR peptide studies | en |
| dc.type | Article | en |
| dc.type.version | publishedVersion | en |
| dcterms.bibliographicCitation.doi | 10.1039/c5ob00034c | |
| dcterms.bibliographicCitation.issue | 11 | |
| dcterms.bibliographicCitation.journaltitle | Organic & biomolecular chemistry : OBC | en |
| dcterms.bibliographicCitation.originalpublishername | Royal Society of Chemistry | de |
| dcterms.bibliographicCitation.originalpublisherplace | Cambridge | de |
| dcterms.bibliographicCitation.pageend | 3181 | |
| dcterms.bibliographicCitation.pagestart | 3171 | |
| dcterms.bibliographicCitation.volume | 13 | |
| tub.accessrights.dnb | free | |
| tub.affiliation | Fak. 2 Mathematik und Naturwissenschaften::Inst. Chemie::FG Biokatalyse | de |
| tub.affiliation.faculty | Fak. 2 Mathematik und Naturwissenschaften | de |
| tub.affiliation.group | FG Biokatalyse | de |
| tub.affiliation.institute | Inst. Chemie | de |
| tub.publisher.universityorinstitution | Technische Universität Berlin |
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