Lubell, William D; Wei, Xiaozheng; Diarra, Sitan; Douchez, Antoine; Dallagnol, Juliana C; Harvey-Lavoie, Simonne; Hébert, Terence E et Chatenet, David 
ORCID: https://orcid.org/0000-0002-7270-4328
(2024).
Tetrasubstituted benzotriazepinones act as β-turn mimics without stereogenic carbons exhibiting allosteric modulation of the urotensin II receptor
In: 37th European Peptide Symposium 14th International Peptide Symposium, August 25-29, 2024, Florence, Italy.
Résumé
β-Turns are privileged structures in peptide recognition events [1].
Nonpeptide small molecules offer potential as topographic mimics
of the form and function of β-turns. We have shown by X-ray
crystallography that tetrasubstituted benzotriazepines can replicate
type I and I0 β-turn geometry due in part to the low barrier for
nitrogen isomerization and dynamic chirality (Figure) [2]. Synthesis,
conformational analysis, and use of tetrasubstituted benzotriazepinones as peptide mimics of urotensin-II receptor modulators will be
presented [3].
References
1. Tyndall, J.D.; Pfeiffer, B.; Abbenante, G.; Fairlie, D.P. Over one hundred peptide-activated G protein-coupled receptors recognize
ligands with turn structure. Chem. Rev. 2005, 105(3), 793–826.
2. Wei, X.; Douchez, A. and Lubell, W. D. 1,3,5,8-Tetrasubstituted
1,3,4-benzotriazepin-2-one scaffolds for β-turn mimicry without chiral carbons: synthesis and conformational analysis. J. Org. Chem.
2023, 88(7), 4,633–48.
3. Wei, X.; Diarra, S.; Douchez, A.; Cunico Dallagnol, J.C.; Hébert, T.E.;
Chatenet, D.; Lubell, W.D. Urotensin II Receptor Modulation with
1, 3, 4-Benzotriazepin-2-one Tetrapeptide Mimics. J. Med. Chem.
2023, 66(20), 14,241–14,262
| Type de document: | Document issu d'une conférence ou d'un atelier |
|---|---|
| Informations complémentaires: | Journal of Peptide Science 30(Suppl.2):3 Meeting Abstract: L03 |
| Mots-clés libres: | - |
| Centre: | Centre INRS-Institut Armand Frappier |
| Date de dépôt: | 06 nov. 2024 04:47 |
| Dernière modification: | 06 nov. 2024 04:47 |
| URI: | https://espace.inrs.ca/id/eprint/16114 |
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