Please use this identifier to cite or link to this item:
http://hdl.handle.net/2445/132717
Title: | Two-electron connection between tryptophan and phenylalanine/tyrosine residues: linked, constrained and stapled peptides through C-H activation processes |
Author: | Mendive Tapia, Lorena Preciado Gallego, Sara García, Jesús Ramón, Rosario Kielland, Nicola Albericio Palomera, Fernando Lavilla Grífols, Rodolfo |
Keywords: | Síntesi en fase sólida Química combinatòria Ressonància magnètica nuclear Solid-phase synthesis Combinatorial chemistry Nuclear magnetic resonance |
Issue Date: | 21-May-2015 |
Publisher: | Nature Publishing Group |
Abstract: | 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. |
Note: | Reproducció del document publicat a: https://doi.org/10.1038/ncoms8160 |
It is part of: | Nature Communications, 2015, vol. 6, p. 7160 |
URI: | http://hdl.handle.net/2445/132717 |
Related resource: | https://doi.org/10.1038/ncoms8160 |
ISSN: | 2041-1723 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
667016.pdf | 1.67 MB | Adobe PDF | View/Open |
This item is licensed under a Creative Commons License