The "Azirine/Oxazolone Method" under Solid-Phase Conditions

• Published in: European journal of organic chemistry Vol. 2004; no. 18; pp. 3820 - 3827
• Main Authors: Stamm, Simon, Heimgartner, Heinz
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2004; WILEY‐VCH Verlag; Wiley
• Subjects: Aminoisobutyric acid (Aib); Azirine; Chemistry; Chemistry, Organic; Inverse peptide synthesis; Oxazolone method; Peptides; Physical Sciences; Science & Technology; Solid-phase synthesis; oxazolone method; SEGMENT; peptides; CARBAMATE LINKER; AMINO-ACID FLUORIDES; solid-phase synthesis; inverse peptide synthesis; SUPPORT; azirine; 3-AMINO-2H-AZIRINES; POLYMER; aminoisobutyric acid (Aib); PEPTIDE-SYNTHESIS; SYNTHONS; EQUIVALENT
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200400330

Aib‐containing peptides have been synthesized from the N‐ to the C‐terminus by the “azirine/oxazolone method” under solid‐phase conditions. In this new and convenient method for the synthesis of sterically demanding peptides on solid phase, 2H‐azirine‐3‐amines are used to introduce aminoisobutyric acid, an α,α‐disubstituted α‐amino acid, into the peptide without the need for further reagents. Segments of naturally occurring peptaibols have been prepared by this method. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)