New synthesis ofcis 5-tert-butyl-L-proline via cuprate. Evaluation as acis proline mimetic in a biological active octapeptide

Carine Aubry (1) , Hassan Oulyadi (1) , Guillaume Dutheuil (1) , Jérôme Leprince (2) , Hubert Vaudry (2) , Xavier Pannecoucke (1) , Jean-Charles Quirion (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Neuroendocrinologie cellulaire et moléculaire

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.

Domains: Chemical Sciences; Medicinal Chemistry; Life Sciences [q-bio]; Cellular Biology; Cell Behavior [q-bio.CB]; Life Sciences [q-bio]; Neurons and Cognition [q-bio.NC]; Neurobiology; Life Sciences [q-bio]; Pharmaceutical sciences; Pharmacology

Carine Aubry, Hassan Oulyadi, Guillaume Dutheuil, Jérôme Leprince, Hubert Vaudry, et al.. New synthesis ofcis 5-tert-butyl-L-proline via cuprate. Evaluation as acis proline mimetic in a biological active octapeptide. Journal of Peptide Science, 2006, 12 (2), pp.154-160. ⟨10.1002/psc.690⟩. ⟨hal-01960646⟩