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The ‘Azirine/Oxazolone Method’ on Solid Phase: Introduction of Various α,α-Disubstituted α-Amino Acids

✍ Scribed by Simon Stamm; Anthony Linden; Heinz Heimgartner

Publisher: John Wiley and Sons
Year: 2006
Tongue: German
Weight: 260 KB
Volume: 89
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200690019

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✦ Synopsis

Peptides containing various a,a-disubstituted a-amino acids, such as a-aminoisobutyric acid (Aib), 1-aminocyclopentane-1-carboxylic acid, a-methylphenylalanine, and 3-amino-3,4,5,6-tetrahydro-2Hpyran-3-carboxylic acid have been synthesized from the N-to the C-terminus by the 'azirine/oxazolone method' under solid-phase conditions. In this convenient method for the synthesis of sterically demanding peptides on solid-phase, 2H-azirin-3-amines are used to introduce the a,a-disubstituted a-amino acids without the need for additional reagents. Furthermore, the synthesis of poly(Aib) sequences has been explored.

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