Enantioselective synthesis of (2S)-2-(4-phosphonophenylmethyl)-3-aminopropanoic acid suitably protected for peptide synthesis

Wang-Qing Liu (1) , Catherine Olszowy (2) , Laurent Bischoff (3) , Christiane Garbay (4)

1 PMC - UMR_S 648 - Pharmacochimie Moléculaire et Cellulaire
2 UPD5 Pharmacie - Université Paris Descartes - Faculté de Pharmacie de Paris
3 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
4 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques

Protected d-β-2-(4-phosphono) phenylalanine was prepared by a multistep synthesis, involving the diastereoselective alkylation of a chiral enolate. This new compound can be further incorporated into peptidic backbone by means of solid-phase peptide synthesis in order to synthesize short peptides adopting β-turn or α-helix conformations.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

Wang-Qing Liu, Catherine Olszowy, Laurent Bischoff, Christiane Garbay. Enantioselective synthesis of (2S)-2-(4-phosphonophenylmethyl)-3-aminopropanoic acid suitably protected for peptide synthesis. Tetrahedron Letters, 2002, 43 (8), pp.1417-1419. ⟨10.1016/S0040-4039(02)00004-7⟩. ⟨hal-02385516⟩