New synthesis of cis 5-tert-butyl-L-proline via cuprate. Evaluation as a cis proline mimetic in a biological active octapeptide.
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.
Aubry
Carine
C
Laboratoire d'Hétérochimie Organique, UMR CNRS 6014, IRCOF, INSA et Université de Rouen, F-76821 Mont-Saint-Aignan, France.
Oulyadi
Hassan
H
Dutheuil
Guillaume
G
Leprince
Jerome
J
Vaudry
Hubert
H
Pannecoucke
Xavier
X
Quirion
Jean-Charles
JC
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
C407508:5-tert-butylproline; D009842:Oligopeptides; D003300:Copper; D011392:Proline