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Synthesis of the protected 6–16 segment of Zervamicin II-2, an application of the Azirine/Oxazolone method


Pradeille, Nicolas; Heimgartner, Heinz (2003). Synthesis of the protected 6–16 segment of Zervamicin II-2, an application of the Azirine/Oxazolone method. Journal of Peptide Science, 9(11-12):827-837.

Abstract

The protected 11 amino acid segment (6–16) of the peptaibol zervamicin II-2 was synthesized by using the ‘azirine/oxazolone method’ for the introduction of all Aib residues. Whereas a 2,2-dimethyl-2H-azirin-3-amine was used as the building block for Aib(7), methyl 2,2-dimethyl-2H-azirine-3-prolinate and -3-(3-hydroxyprolinate) proved to be ideally suited as dipeptide synthons for the introduction of Aib-Pro and Aib-Hyp, respectively. The coupling of Z-protected amino acids or peptide acids with the 2H-azirin-3-amines were performed in 75% to quantitative yield.

Abstract

The protected 11 amino acid segment (6–16) of the peptaibol zervamicin II-2 was synthesized by using the ‘azirine/oxazolone method’ for the introduction of all Aib residues. Whereas a 2,2-dimethyl-2H-azirin-3-amine was used as the building block for Aib(7), methyl 2,2-dimethyl-2H-azirine-3-prolinate and -3-(3-hydroxyprolinate) proved to be ideally suited as dipeptide synthons for the introduction of Aib-Pro and Aib-Hyp, respectively. The coupling of Z-protected amino acids or peptide acids with the 2H-azirin-3-amines were performed in 75% to quantitative yield.

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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:2003
Deposited On:19 Aug 2013 06:43
Last Modified:05 Apr 2016 16:55
Publisher:Wiley-Blackwell
ISSN:1075-2617
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/psc.522
PubMed ID:14658802

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