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Anwendung der Azirin/Oxazolon-Methode in der Peptid-Chemie: Synthese von Modell-Tripeptiden


Wipf, Peter; Heimgartner, Heinz (1988). Anwendung der Azirin/Oxazolon-Methode in der Peptid-Chemie: Synthese von Modell-Tripeptiden. Helvetica Chimica Acta, 71(1):140-154.

Abstract

The Azirine/Oxazolone Method in Peptide Chemistry: Synthesis of Tripeptide Models
Tripeptides 5, containing an alpha,alpha-disubstituted alpha-amino acid and ethyl p-aminobenzoate, were synthesized in high yield by application of the azirine/oxazolone method (Table 2). In this versatile approach for the incorporation of disubstituted residues into the peptide chain, N-protected peptides or amino acids are coupled with 2,2-dialkyl-3-amino-2H-azirines and, after the selective hydrolysis of the newly formed C-terminal amide bond, further condensed with amino components via in situ generated oxazole-5(4H)-ones in the presence of additives (Scheme 1). A comparison with conventional procedures clearly demonstrates the advantages of this new method that works equally well with beta-branched, cyclic, or acyclic disubstituted amino acids.

Abstract

The Azirine/Oxazolone Method in Peptide Chemistry: Synthesis of Tripeptide Models
Tripeptides 5, containing an alpha,alpha-disubstituted alpha-amino acid and ethyl p-aminobenzoate, were synthesized in high yield by application of the azirine/oxazolone method (Table 2). In this versatile approach for the incorporation of disubstituted residues into the peptide chain, N-protected peptides or amino acids are coupled with 2,2-dialkyl-3-amino-2H-azirines and, after the selective hydrolysis of the newly formed C-terminal amide bond, further condensed with amino components via in situ generated oxazole-5(4H)-ones in the presence of additives (Scheme 1). A comparison with conventional procedures clearly demonstrates the advantages of this new method that works equally well with beta-branched, cyclic, or acyclic disubstituted amino acids.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1988
Deposited On:14 May 2014 09:06
Last Modified:05 Apr 2016 17:50
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19880710118

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