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The ‘Azirine/Oxazolone Method’ on solid phase: Introduction of various alpha,alpha-disubstituted alpha-Amino Acids


Stamm, Simon; Linden, Anthony; Heimgartner, Heinz (2006). The ‘Azirine/Oxazolone Method’ on solid phase: Introduction of various alpha,alpha-disubstituted alpha-Amino Acids. Helvetica Chimica Acta, 89(1):1-15.

Abstract

Peptides containing various alpha,alpha-disubstituted alpha-amino acids, such as alpha-aminoisobutyric acid (Aib), 1-aminocyclopentane-1-carboxylic acid, alpha-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 alpha,alpha-disubstituted alpha-amino acids without the need for additional reagents. Furthermore, the synthesis of poly(Aib) sequences has been explored.

Abstract

Peptides containing various alpha,alpha-disubstituted alpha-amino acids, such as alpha-aminoisobutyric acid (Aib), 1-aminocyclopentane-1-carboxylic acid, alpha-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 alpha,alpha-disubstituted alpha-amino acids without the need for additional reagents. Furthermore, the synthesis of poly(Aib) sequences has been explored.

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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:2006
Deposited On:22 May 2012 07:18
Last Modified:05 Apr 2016 15:47
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Swiss National Science Foundation , F. Hoffmann-La Roche AG, Basel
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/hlca.200690019

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