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Synthesis of Aib-containing cyclopeptides via the 'azirine/oxazolone method'


Dannecker-Dörig, I; Linden, A; Heimgartner, H (2009). Synthesis of Aib-containing cyclopeptides via the 'azirine/oxazolone method'. Collection of Czechoslovak Chemical Communications, 74(6):901-925.

Abstract

The cyclic pentapeptide cyclo[Gly-Phe(2Me)-Aib-Aib-Gly], containing three α,α-disubstituted α-amino acids, was prepared by cyclization of H-Gly-Phe(2Me)-Aib-Aib-Gly-OH with diphenylphosporazidate (DPPA) in 60% yield. The synthesis of the linear precursor was performed by using the ‘azirine/oxazolone method’, in which the α,α-disubstituted α-amino acids were introduced by coupling of the corresponding amino or peptide acid with a 2,2-disubstituted 3-amino-2H-azirine. Whereas the cyclization of an analogous hexapeptide afforded the cyclopeptide in 42% yield, the corresponding tetrapeptide yielded a 1:2 mixture of the monomeric and dimeric cyclopeptide. In the case of the tripeptide H-Gly-Phe(2Me)-Aib-OH,
the cyclization with DPPA led to the dimeric cyclohexapeptide exclusively.

Abstract

The cyclic pentapeptide cyclo[Gly-Phe(2Me)-Aib-Aib-Gly], containing three α,α-disubstituted α-amino acids, was prepared by cyclization of H-Gly-Phe(2Me)-Aib-Aib-Gly-OH with diphenylphosporazidate (DPPA) in 60% yield. The synthesis of the linear precursor was performed by using the ‘azirine/oxazolone method’, in which the α,α-disubstituted α-amino acids were introduced by coupling of the corresponding amino or peptide acid with a 2,2-disubstituted 3-amino-2H-azirine. Whereas the cyclization of an analogous hexapeptide afforded the cyclopeptide in 42% yield, the corresponding tetrapeptide yielded a 1:2 mixture of the monomeric and dimeric cyclopeptide. In the case of the tripeptide H-Gly-Phe(2Me)-Aib-OH,
the cyclization with DPPA led to the dimeric cyclohexapeptide exclusively.

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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:19 May 2009
Deposited On:25 Nov 2009 08:29
Last Modified:21 Nov 2017 14:27
Publisher:Akademie Ved Ceske Republiky
ISSN:0010-0765
Funders:Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1135/cccc2009017

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