Catalysis of Thiol–Thioester Exchange by Water-Soluble Alkyldiselenols Applied to the Synthesis of Peptide Thioesters and SEA-Mediated Ligation
| Autor: | Oleg Melnyk, Marine Cargoët, Vangelis Agouridas, Rémi Desmet, Hervé Drobecq, Annick Blanpain, Vincent Diemer, Benoît Snella |
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| Přispěvatelé: | Chimie organique et bioorganique (COB), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Ecole Nationale Supérieure de Chimie de Mulhouse-Centre National de la Recherche Scientifique (CNRS), Institut de biologie de Lille - IBL (IBLI), Université de Lille, Sciences et Technologies-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Université de Lille, Droit et Santé-Centre National de la Recherche Scientifique (CNRS), IFR 142 (IFR 142), Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2018 |
| Předmět: |
Tris
Phosphines Kinetics Peptide 010402 general chemistry Thioester 01 natural sciences Catalysis Structure-Activity Relationship chemistry.chemical_compound [CHIM.ANAL]Chemical Sciences/Analytical chemistry Organoselenium Compounds [CHIM]Chemical Sciences Structure–activity relationship Sulfhydryl Compounds ComputingMilieux_MISCELLANEOUS chemistry.chemical_classification Molecular Structure [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Organic Chemistry Water Esters Hydrogen-Ion Concentration Combinatorial chemistry 0104 chemical sciences 3. Good health Solubility chemistry Thiol lipids (amino acids peptides and proteins) Peptides Phosphine |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2018, 83 (20), pp.12584-12594. ⟨10.1021/acs.joc.8b01903⟩ |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | N-Alkyl bis(2-selanylethyl)amines catalyze the synthesis of peptide thioesters or peptide ligation from bis(2-sulfanylethyl)amido (SEA) peptides. These catalysts are generated in situ by reduction of the corresponding cyclic diselenides by tris(2-carboxyethyl)phosphine. They are particularly efficient at pH 4.0 by accelerating the thiol-thioester exchange processes, which are otherwise rate-limiting at this pH. By promoting SEA-mediated reactions at mildly acidic pH, they facilitate the synthesis of complex peptides such as cyclic O-acyl isopeptides that are otherwise hardly accessible. |
| Databáze: | OpenAIRE |
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