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Synthesis of Bis-Aminoazirines and their Application in Peptide Synthesis


Köttgen, P; Linden, A; Heimgartner, H (2009). Synthesis of Bis-Aminoazirines and their Application in Peptide Synthesis. Acta Chimica Slovenica, 56(3):591-602.

Abstract

The 'cyclohexane-bridged' bis-(3-amino-2H-azirines) cis- and trans-N,N’-dimethyl-N,N’-diphenyl-1,7-diazadispiro[2.2.2.2]deca-1,7-diene-2,8-diamine (cis-21 and trans-21) were synthesized from the corresponding bis-thioamide 20 by consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO) and NaN3. The reaction of these bis-azirines with different natural α-amino acids gave peptide amides 23. In addition, hydrolysis of the C-terminal amide groups of 23c and subsequent coupling with the Aib synthon 2, i.e., 2,2,N-trimethyl-N-phenyl-2H-azirin-3-amine, showed the applicability of building blocks 21 for peptide synthesis and peptide chain ligation.

Abstract

The 'cyclohexane-bridged' bis-(3-amino-2H-azirines) cis- and trans-N,N’-dimethyl-N,N’-diphenyl-1,7-diazadispiro[2.2.2.2]deca-1,7-diene-2,8-diamine (cis-21 and trans-21) were synthesized from the corresponding bis-thioamide 20 by consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO) and NaN3. The reaction of these bis-azirines with different natural α-amino acids gave peptide amides 23. In addition, hydrolysis of the C-terminal amide groups of 23c and subsequent coupling with the Aib synthon 2, i.e., 2,2,N-trimethyl-N-phenyl-2H-azirin-3-amine, showed the applicability of building blocks 21 for peptide synthesis and peptide chain ligation.

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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:18 September 2009
Deposited On:25 Nov 2009 14:53
Last Modified:06 Dec 2017 21:46
Publisher:Slovenian Chemical Society
ISSN:1318-0207
Funders:University of Zurich
Additional Information:OPEN ACCESS
Official URL:http://acta.chem-soc.si/56/56-03-591.pdf

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