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Synthesis of Poly-Aib Oligopeptides and Aib-Containing Peptides via the 'Azirine/Oxazolone Method', and their crystal structures


Dannecker-Dörig, I; Linden, A; Heimgartner, H (2011). Synthesis of Poly-Aib Oligopeptides and Aib-Containing Peptides via the 'Azirine/Oxazolone Method', and their crystal structures. Helvetica Chimica Acta, 94(6):993-1011.

Abstract

The protected poly-Aib oligopeptides Z-(Aib)n-N(Me)Ph with n = 2 – 6 were prepared according to the 'azirine/oxazolone method', i.e., by coupling amino or peptide acids with 2,2,N-trimethyl-N-phenyl-2H-azirin-3-amine (1a) as an Aib synthon (Scheme 2). Following the same concept, the segments Z-(Aib)3-OH (9) and H-L-Pro-(Aib)3-N(Me)Ph (20) were synthesized, and their subsequent coupling with N,N’-dicyclohexylcarbodiimide (DCC)/ZnCl2 led to the protected heptapeptide Z-(Aib)3-L-Pro-(Aib)3-N(Me)Ph (21; Scheme 3). The crystal structures of the poly-Aib oligopeptide amides were established by X-ray crystallography confirming the 310-helical conformation of Aib peptides.

Abstract

The protected poly-Aib oligopeptides Z-(Aib)n-N(Me)Ph with n = 2 – 6 were prepared according to the 'azirine/oxazolone method', i.e., by coupling amino or peptide acids with 2,2,N-trimethyl-N-phenyl-2H-azirin-3-amine (1a) as an Aib synthon (Scheme 2). Following the same concept, the segments Z-(Aib)3-OH (9) and H-L-Pro-(Aib)3-N(Me)Ph (20) were synthesized, and their subsequent coupling with N,N’-dicyclohexylcarbodiimide (DCC)/ZnCl2 led to the protected heptapeptide Z-(Aib)3-L-Pro-(Aib)3-N(Me)Ph (21; Scheme 3). The crystal structures of the poly-Aib oligopeptide amides were established by X-ray crystallography confirming the 310-helical conformation of Aib peptides.

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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:2011
Deposited On:04 Aug 2011 08:09
Last Modified:07 Dec 2017 08:43
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Stipendienfonds der Basler Chemischen Industrie, Swiss National Science Foundation, F. Hoffmann-La Roche AG
Publisher DOI:https://doi.org/10.1002/hlca.201100116

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