Novel N-(2,2-Dimethyl-2H-azirin-3-yl)-L-prolinates as Aib-Pro Synthons

✍ Scribed by Simon Stamm; Heinz Heimgartner

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: German
• Weight: 169 KB
• Volume: 89
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200690178

✦ Synopsis

The syntheses of phenacyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate and allyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate are reported. Reactions of these 2H-azirin-3-amine derivatives with Z-protected amino acids have shown them to be suitable synthons for the Aib-Pro unit in peptide synthesis. After incorporation into the peptide by means of the azirine/oxazolone method, the C-termini of the resulting peptides were deprotected selectively with Zn in AcOH or by a mild Pd 0 -promoted procedure, respectively.

Recently, we adapted the azirine/oxazolone method to solid-phase conditions, in order to additionally profit from their benefits [19]. Moreover, it was shown that, where two conformers were observed, only the signals of the major conformer are shown. The ratio of the two conformers is given in parentheses. MS (m/z (rel.%)): Bruker ESQUIRE-LC quadrupole ion-trap instrument. Abbreviations: Aib: a