Synthesis of Poly-Aib Oligopeptides and Aib-Containing Peptides via the ‘Azirine/Oxazolone Method’, and Their Crystal Structures

✍ Scribed by Ingeborg Dannecker-Dörig; Anthony Linden; Heinz Heimgartner

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 348 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201100116

✦ Synopsis

The protected poly-Aib oligopeptides Z-(Aib) n -N(Me)Ph with n ¼ 2 -6 were prepared according to the azirine/oxazolone method, i.e., by coupling amino or peptide acids with 2,2,N-trimethyl-N-phenyl-2H-azirin-3-amine (1a) as an Aib synthon (Scheme 2). Following the same concept, the segments Z-(Aib) 3 -OH ( 9) and H-l-Pro-(Aib) 3 -N(Me)Ph (20) were synthesized, and their subsequent coupling with N,N'-dicyclohexylcarbodiimide (DCC)/ZnCl 2 led to the protected heptapeptide Z-(Aib) 3 -l-Pro-(Aib) 3 -N(Me)Ph (21; Scheme 3). The crystal structures of the poly-Aib oligopeptide amides were established by X-ray crystallography confirming the 3 10 -helical conformation of Aib peptides.