title: Efficient synthesis of both diastereomers of β,γ-diamino acids from phenylalanine and tryptophan.
abstract: We synthesized in a few steps both diastereomers of orthogonally protected β,γ-diamino acids starting from L-phenylalanine or L-tryptophan. These final compounds are interesting building blocks for peptide synthesis and foldamer chemistry. The key step is a Blaise reaction performed under ultrasound conditions.
authors.affiliation: Faculté des Sciences d'Orsay, Univ. Paris-Sud, Laboratoire de Méthodologie, Synthèse et Molécules Thérapeutiques, ICMMO, UMR 8182, CNRS, Université Paris-Saclay, Bât 410, Orsay, 91405, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Auberger
authors.affiliation: Faculté des Sciences d'Orsay, Univ. Paris-Sud, Laboratoire de Méthodologie, Synthèse et Molécules Thérapeutiques, ICMMO, UMR 8182, CNRS, Université Paris-Saclay, Bât 410, Orsay, 91405, France.
authors.forename: Andrii
authors.initials: A
authors.lastname: Stanovych
authors.affiliation: Faculté des Sciences d'Orsay, Univ. Paris-Sud, Laboratoire de Méthodologie, Synthèse et Molécules Thérapeutiques, ICMMO, UMR 8182, CNRS, Université Paris-Saclay, Bât 410, Orsay, 91405, France.
authors.forename: Sophie
authors.initials: S
authors.lastname: Thétiot-Laurent
authors.affiliation: Faculté des Sciences d'Orsay, Univ. Paris-Sud, Laboratoire de Méthodologie, Synthèse et Molécules Thérapeutiques, ICMMO, UMR 8182, CNRS, Université Paris-Saclay, Bât 410, Orsay, 91405, France.
authors.forename: Régis
authors.initials: R
authors.lastname: Guillot
authors.affiliation: Faculté des Sciences d'Orsay, Univ. Paris-Sud, Laboratoire de Méthodologie, Synthèse et Molécules Thérapeutiques, ICMMO, UMR 8182, CNRS, Université Paris-Saclay, Bât 410, Orsay, 91405, France.
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky
authors.affiliation: Sanofi Recherche et Développement, 1 avenue Pierre Brossolette, 91385, Chilly Mazarin Cedex, France.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Cote des Combes
authors.affiliation: Sanofi Recherche et Développement, 1 avenue Pierre Brossolette, 91385, Chilly Mazarin Cedex, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Pacaud
authors.affiliation: Sanofi Recherche et Développement, 1 avenue Pierre Brossolette, 91385, Chilly Mazarin Cedex, France.
authors.forename: Ingrid
authors.initials: I
authors.lastname: Devillers
authors.affiliation: Faculté des Sciences d'Orsay, Univ. Paris-Sud, Laboratoire de Méthodologie, Synthèse et Molécules Thérapeutiques, ICMMO, UMR 8182, CNRS, Université Paris-Saclay, Bât 410, Orsay, 91405, France. valerie.alezra@u-psud.fr.
authors.forename: Valérie
authors.initials: V
authors.lastname: Alezra
mesh_terms: D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000138:chemical synthesis* / Q000737:chemistry*; D000069453:Ultrasonic Waves
chemical_list: D010649:Phenylalanine; D014364:Tryptophan
keywords: Asymmetric synthesis; Blaise reaction; Non proteinogenic amino acid synthesis; β-amino acid; γ-amino acid