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The "Azirine/Oxazolone Method" under solid-phase conditions


Stamm, Simon; Heimgartner, Heinz (2004). The "Azirine/Oxazolone Method" under solid-phase conditions. European Journal of Organic Chemistry, 2004(18):3820-3827.

Abstract

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.

Abstract

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.

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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
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry
Language:English
Date:2004
Deposited On:13 Aug 2013 15:09
Last Modified:18 Aug 2018 10:51
Publisher:Wiley-Blackwell
ISSN:1099-0690
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/ejoc.200400330
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel

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