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3-amino-2h-azirines in the synthesis of peptides: tetrapeptides with alpha,alpha-disubstituted alpha-amino acids


Sahebi, Mostafa; Wipf, Peter; Heimgartner, Heinz (1989). 3-amino-2h-azirines in the synthesis of peptides: tetrapeptides with alpha,alpha-disubstituted alpha-amino acids. Tetrahedron, 45(10):2999-3010.

Abstract

3-Amino-2,2-dialkyl-2H-azirines 1 are synthons for alpha,alpha-disubstituted alpha-amino acids. Tetrapeptides 15, containing two such amino acids, were synthesized in high yield by application of the "azirine/oxazolone-method". In this versatile approach for the incorporation of di-substituted amino acids into the peptide chain, N-protected amino acids or peptides are coupled with 3-amino-2H-azirines 1. After selective hydrolysis of the newly formed C-terminal amide, condensation with valine-benzylester was achieved via in situ generated oxazole-5(4H)-ones in the presence of hydroxybenzotriazole. The conformational properties of tetrapeptides 15 are discussed on the basis of NMR- and CD-spectra. It is shown that alpha,alpha-disubstitution favours the formation of beta-turns even in very short oligopeptides. The "azirine/oxazolone-method" offers an efficient stra- tegy for the synthesis of peptide-models used for con- formational studies.

Abstract

3-Amino-2,2-dialkyl-2H-azirines 1 are synthons for alpha,alpha-disubstituted alpha-amino acids. Tetrapeptides 15, containing two such amino acids, were synthesized in high yield by application of the "azirine/oxazolone-method". In this versatile approach for the incorporation of di-substituted amino acids into the peptide chain, N-protected amino acids or peptides are coupled with 3-amino-2H-azirines 1. After selective hydrolysis of the newly formed C-terminal amide, condensation with valine-benzylester was achieved via in situ generated oxazole-5(4H)-ones in the presence of hydroxybenzotriazole. The conformational properties of tetrapeptides 15 are discussed on the basis of NMR- and CD-spectra. It is shown that alpha,alpha-disubstitution favours the formation of beta-turns even in very short oligopeptides. The "azirine/oxazolone-method" offers an efficient stra- tegy for the synthesis of peptide-models used for con- formational studies.

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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:English
Date:1989
Deposited On:09 Apr 2014 15:35
Last Modified:08 Dec 2017 05:09
Publisher:Elsevier
ISSN:0040-4020
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1016/S0040-4020(01)80127-7

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