title: New synthesis of cis 5-tert-butyl-L-proline via cuprate. Evaluation as a cis proline mimetic in a biological active octapeptide.
abstract: cis 5-tert-butyl-L-proline (Cbp) was prepared rapidly and efficiently by the addition of low-valent tert-butyl cuprate to an aminal derived from proline. [Cbp(2), D-Leu(5)]-OP was then synthesized, showing a predominant cis peptide bond conformation, as confirmed by NMR.
authors.affiliation: Laboratoire d'Hétérochimie Organique, UMR CNRS 6014, IRCOF, INSA et Université de Rouen, F-76821 Mont-Saint-Aignan, France.
authors.forename: Carine
authors.initials: C
authors.lastname: Aubry
authors.forename: Hassan
authors.initials: H
authors.lastname: Oulyadi
authors.forename: Guillaume
authors.initials: G
authors.lastname: Dutheuil
authors.forename: Jerome
authors.initials: J
authors.lastname: Leprince
authors.forename: Hubert
authors.initials: H
authors.lastname: Vaudry
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
authors.forename: Jean-Charles
authors.initials: JC
authors.lastname: Quirion
mesh_terms: D003300:Copper / Q000737:chemistry*; D018716:Molecular Mimicry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: C407508:5-tert-butylproline; D009842:Oligopeptides; D003300:Copper; D011392:Proline