title: Rapid and scalable synthesis of innovative unnatural α,β or γ-amino acids functionalized with tertiary amines on their side-chains.
abstract: 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.
authors.affiliation: Laboratoire d'Innovation Thérapeutique, UMR7200, CNRS, Université de Strasbourg, faculté de pharmacie, 74, route du Rhin, 67401 Illkirch, France. fbihel@unistra.fr.
authors.forename: Séverine
authors.initials: S
authors.lastname: Schneider
authors.forename: Hussein
authors.initials: H
authors.lastname: Ftouni
authors.forename: Songlin
authors.initials: S
authors.lastname: Niu
authors.forename: Martine
authors.initials: M
authors.lastname: Schmitt
authors.forename: Frédéric
authors.initials: F
authors.lastname: Simonin
authors.forename: Frédéric
authors.initials: F
authors.lastname: Bihel
mesh_terms: D000577:Amides / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002384:Catalysis; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques / Q000191:economics / Q000379:methods*
chemical_list: D000577:Amides; D000588:Amines; D000596:Amino Acids; D012428:Ruthenium; D001120:Arginine; D009952:Ornithine; D008239:Lysine