2026-04-17T14:45:55Zhttps://recercat.cat/oai/request

oai:recercat.cat:2445/1327172025-12-04T21:44:01Zcom_2072_1057col_2072_478917col_2072_478933

urn:hdl:2445/132717 Two-electron connection between tryptophan and phenylalanine/tyrosine residues: linked, constrained and stapled peptides through C-H activation processes Mendive Tapia, Lorena Preciado Gallego, Sara García, Jesús Ramón, Rosario Kielland, Nicola Albericio Palomera, Fernando Lavilla Grífols, Rodolfo Síntesi en fase sólida Química combinatòria Ressonància magnètica nuclear Solid-phase synthesis Combinatorial chemistry Nuclear magnetic resonance Natural peptides show high degrees of specificity in their biological action. However, their therapeutical profile is severely limited by their conformational freedom and metabolic instability. Stapled peptides constitute a solution to these problems and access to these structures lies on a limited number of reactions involving the use of non-natural amino acids. Here, we describe a synthetic strategy for the preparation of unique constrained peptides featuring a covalent bond between tryptophan and phenylalanine or tyrosine residues. The preparation of such peptides is achieved in solution and on solid phase directly from the corresponding sequences having an iodo-aryl amino acid through an intramolecular palladium-catalysed C-H activation process. Moreover, complex topologies arise from the internal stapling of cyclopeptides and double intramolecular arylations within a linear peptide. Finally, as a proof of principle, we report the application to this new stapling method to relevant biologically active compounds. 2019-05-06T09:46:47Z 2019-05-06T09:46:47Z 2015-05-21 2019-05-06T09:46:48Z info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Reproducció del document publicat a: https://doi.org/10.1038/ncoms8160 Nature Communications, 2015, vol. 6, p. 7160 https://doi.org/10.1038/ncoms8160 cc-by (c) Mendive Tapia, Lorena et al., 2015 http://creativecommons.org/licenses/by/3.0/es info:eu-repo/semantics/openAccess Nature Publishing Group Articles publicats en revistes (Química Inorgànica i Orgànica)