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Ein neues 3-Amino-2H-azirin als Aib-Pro-Baustein: Synthese des C-terminalen Nonapeptids von Trichovirin I 1B


Luykx, Roeland; Bucher, Christoph B; Linden, Anthony; Heimgartner, Heinz (1996). Ein neues 3-Amino-2H-azirin als Aib-Pro-Baustein: Synthese des C-terminalen Nonapeptids von Trichovirin I 1B. Helvetica Chimica Acta, 79(2):527-540.

Abstract

The synthesis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate (3), a novel 3-amino-2H-azirine, is described (Scheme 2). It is shown that the reaction of COCI, with thioamide 5 is remarkably faster than with the corresponding amide 4, and the yield of 3 is much better in the synthesis starting with 5. The 3-amino-2H-azirine 3 has been used as a building block of the dipeptide moieties Aib-Pro in the synthesis of nonapeptide 17 (Schemes 4 and 5), the C-terminal 6-14 segment of the peptaibole trichovirin I 1B.The structure of 17 was established by single-crystal X-ray crystallography (Figs. 1 and 2).

Abstract

The synthesis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate (3), a novel 3-amino-2H-azirine, is described (Scheme 2). It is shown that the reaction of COCI, with thioamide 5 is remarkably faster than with the corresponding amide 4, and the yield of 3 is much better in the synthesis starting with 5. The 3-amino-2H-azirine 3 has been used as a building block of the dipeptide moieties Aib-Pro in the synthesis of nonapeptide 17 (Schemes 4 and 5), the C-terminal 6-14 segment of the peptaibole trichovirin I 1B.The structure of 17 was established by single-crystal X-ray crystallography (Figs. 1 and 2).

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Additional indexing

Other titles:A New 3-Amino-2H-azirine as an Aib-Pro Synthon: Synthesis of the C-Terminal Nonapeptide of Trichovirin I 1B
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1996
Deposited On:25 Nov 2013 08:21
Last Modified:05 Apr 2016 17:11
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19960790220

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