Titre : Multicomponent Reactions in Macrocyclization and Bioconjugation Chemistry
Endroit: Pavillon Roger-Gaudry, Salle N-515
Hôte: William Lubell
Résumé : Multicomponent reactions have lately evolved from versatile methods for the synthesis of small molecules to powerful tools for the post-synthetic derivatization of peptides1 and proteins.2 This lecture highlights the most recent multicomponent transformations conducted at UH and IPB to covalently modify peptides and proteins. These transformations include the multicomponent labeling and stapling of peptides by means of the Petasis reaction as well as the utilization of the Ugi and Ugi-Smiles multicomponent reactions for the simultaneous lipidation/PEGylation and cyclization of peptides.3 Finally, our recent endeavor on the development of antibacterial glycoconjugate vaccine candidates by means of a multicomponent polysaccharide-protein conjugation is described.2 (Voir PDF)
1 (a) C. J. White, A. K. Yudin, Nature Chem. 2011, 3, 509. (b) A. V. Vasco, C. S. Pérez, F. E. Morales, H. E. Garay, D. Vasilev, J. A. Gavín, L. A. Wessjohann, D. G. Rivera, J. Org. Chem. 2015, 80, 6697.
2 Y. Méndez, J. Chang, A. R. Humpierre, A. Zanuy, R. Garrido, A. V. Vasco, J. Pedroso, D. Santana, L. M. Rodríguez, D. García-Rivera, Y. Valdés, V. Vérez-Bencomo, D. G. Rivera, Chem. Sci. 2018, 9, 2581.
3 (a) M. C. Morejón, A. Laub, G. N. Kaluđerović, A. R. Puentes, A. N. Hmedat, A. J.; Otero-González, D. G. Rivera, L. A. Wessjohann, Org. Biomol. Chem. 2017, 15, 3628. (b) M. C. Morejón, A. Laub, B. Westermann, D. G. Rivera, L. A. Wessjohann, Org. Lett. 2016, 18, 4096