Trifluoromethylated Proline Surrogates as Part of "Pro-Pro" Turn-Inducing Templates
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Tartalom: http://real.mtak.hu/114013/
Archívum: REAL
Gyűjtemény: Status = Published
Subject = Q Science / természettudomány: QH Natural history / természetrajz: QH301 Biology / biológia: QH3011 Biochemistry / biokémia
Type = Article
Cím:
Trifluoromethylated Proline Surrogates as Part of "Pro-Pro" Turn-Inducing Templates
Létrehozó:
Gadais, Charlène
Van holsbeeck, Kevin
Moors, Samuel L. C.
Buyst, Dieter
Fehér, Krisztina
Kiadó:
Wiley-VCH GmbH
Dátum:
2019
Téma:
QH3011 Biochemistry / biokémia
Tartalmi leírás:
Proline is often found as a turn inducer in peptide or protein domains. Exploitation of its restricted conformational freedom led to the development of the d-Pro-l-Pro (corresponding to (R)-Pro-(S)-Pro) segment as a "templating" unit, frequently used in the design of beta-hairpin peptidomimetics, in which conformational stability is, however, inherently linked to the cis-trans isomerization of the prolyl amide bonds. In this context, the stereoelectronic properties of the CF3 group can aid in conformational control. Herein, the impact of alpha-trifluoromethylated proline analogues is examined for the design of enhanced beta-turn inducers. A theoretical conformational study permitted the dipeptide (R)-Pro-(R)-TfmOxa (TfmOxa: 2-trifluoromethyloxazolidine-2-carboxylic acid) to be selected as a template with an increased trans-cis rotational energy barrier. NMR spectroscopic analysis of the Ac-(R)-Pro-(R)-TfmOxa-(S)-Val-OtBu beta-turn model, obtained through an original synthetic pathway, validated the prevalence of a major trans-trans conformer and indicated the presence of an internal hydrogen bond. Altogether, it was shown that the (R)-Pro-(R)-TfmOxa template fulfilled all crucial beta-turn-inducer criteria.
Nyelv:
angol
Típus:
Article
PeerReviewed
info:eu-repo/semantics/article
Formátum:
text
Azonosító:
Gadais, Charlène and Van holsbeeck, Kevin and Moors, Samuel L. C. and Buyst, Dieter and Fehér, Krisztina (2019) Trifluoromethylated Proline Surrogates as Part of "Pro-Pro" Turn-Inducing Templates. CHEMBIOCHEM, 20 (19). pp. 2513-2518. ISSN 1439-4227 (print); 1439-7633 (online)
Kapcsolat:
MTMT:30761451 10.1002/cbic.201900294