Rapid and scalable synthesis of innovative unnatural α,β or γ-amino acids functionalized with tertiary amines on their side-chains.
Fiche publication
Date publication
juillet 2015
Journal
Organic & biomolecular chemistry
Auteurs
Membres identifiés du Cancéropôle Est :
Dr SIMONIN Frédéric
Tous les auteurs :
Schneider S, Ftouni H, Niu S, Schmitt M, Simonin F, Bihel F
Lien Pubmed
Résumé
We report a selective ruthenium catalyzed reduction of tertiary amides on the side chain of Fmoc-Gln-OtBu derivatives, leading to innovative unnatural α,β or γ-amino acids functionalized with tertiary amines. Rapid and scalable, this process allowed us to build a library of basic unnatural amino acids at the gram-scale and directly usable for liquid- or solid-phase peptide synthesis. The diversity of available tertiary amines allows us to modulate the physicochemical properties of the resulting amino acids, such as basicity or hydrophobicity.
Mots clés
Amides, chemistry, Amines, chemical synthesis, Amino Acids, chemical synthesis, Arginine, analogs & derivatives, Catalysis, Lysine, analogs & derivatives, Ornithine, analogs & derivatives, Oxidation-Reduction, Ruthenium, chemistry, Solid-Phase Synthesis Techniques, economics
Référence
Org. Biomol. Chem.. 2015 Jul;13(25):7020-6