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The 'Azirine/Oxazolone Method' in peptaibol synthesis: preparation of a Dderivative of trichotoxin A-50 (G)


Altherr, W; Linden, A; Heimgartner, H (2007). The 'Azirine/Oxazolone Method' in peptaibol synthesis: preparation of a Dderivative of trichotoxin A-50 (G). Chemistry & Biodiversity, 4:1144-1169.

Abstract

The synthesis of a mixture of epimeric derivatives of the peptaibol trichotoxin A-50 (G) is described. The 'azirine/oxazolone method' has been used as a superior method for the introduction of the Aib as well as the Iva units into the peptide chain. In this protocol, 2,2-disubstituted 2H-azirin-3-amines are the synthons for 2,2-disubstituted glycines, which undergo coupling with N-protected amino or peptide acids in high yield, and without any need of coupling reagents. The problem of the instability of the amide function of the Gln side chain under the conditions of the acid-catalyzed hydrolysis of Z-Gln-(Aib)n-N(Me)Ph was solved by using an appropriate protecting group for the amide function of the Gln side chain, e.g., the triphenylmethyl (trityl; Tr) group. The structures of two intermediate peptides, i.e., the segments comprising residues 1–5 and 10–13, resp., were established by X-ray crystallography.

Abstract

The synthesis of a mixture of epimeric derivatives of the peptaibol trichotoxin A-50 (G) is described. The 'azirine/oxazolone method' has been used as a superior method for the introduction of the Aib as well as the Iva units into the peptide chain. In this protocol, 2,2-disubstituted 2H-azirin-3-amines are the synthons for 2,2-disubstituted glycines, which undergo coupling with N-protected amino or peptide acids in high yield, and without any need of coupling reagents. The problem of the instability of the amide function of the Gln side chain under the conditions of the acid-catalyzed hydrolysis of Z-Gln-(Aib)n-N(Me)Ph was solved by using an appropriate protecting group for the amide function of the Gln side chain, e.g., the triphenylmethyl (trityl; Tr) group. The structures of two intermediate peptides, i.e., the segments comprising residues 1–5 and 10–13, resp., were established by X-ray crystallography.

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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:2007
Deposited On:04 Nov 2011 13:19
Last Modified:05 Apr 2016 15:04
Publisher:Verlag Helvetica Chimica Acta
ISSN:1612-1872
Funders:Swiss National Science Foundation , Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/cbdv.200790102

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