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Synthesis of conformationally restricted cyclic pentadepsipeptides via direct amide cyclization


Koch, Kristian N; Linden, Anthony; Heimgartner, Heinz (2001). Synthesis of conformationally restricted cyclic pentadepsipeptides via direct amide cyclization. Tetrahedron, 57(12):2311-2326.

Abstract

The 2,2-disubstituted 2H-azirin-3-amines 6 (3-amino-2H-azirines) were used as building blocks for alpha,alpha-disubstituted alpha-amino acids in the preparation of 16-membered cyclic depsipeptides 14. The linear precursors containing four alpha,alpha-disubstituted alpha-amino acids, the pentapeptides 13, were synthesized starting with beta-hydroxy acids 5 via the 'azirine/oxazolone method'. The cyclic depsipeptides 14 were formed via 'direct amide cyclization' and the influence of several factors on this cyclization was investigated in the following way: (a) using the same composition of alpha,alpha-disubstituted alpha-amino acids, but changing their respective positions in the peptide chain; (b) using different C-terminal alpha,alpha-disubstituted alpha-amino acids in the peptide chain; (c) using different beta-hydroxy acids; and (d) using different diastereoisomers of the peptides.

Abstract

The 2,2-disubstituted 2H-azirin-3-amines 6 (3-amino-2H-azirines) were used as building blocks for alpha,alpha-disubstituted alpha-amino acids in the preparation of 16-membered cyclic depsipeptides 14. The linear precursors containing four alpha,alpha-disubstituted alpha-amino acids, the pentapeptides 13, were synthesized starting with beta-hydroxy acids 5 via the 'azirine/oxazolone method'. The cyclic depsipeptides 14 were formed via 'direct amide cyclization' and the influence of several factors on this cyclization was investigated in the following way: (a) using the same composition of alpha,alpha-disubstituted alpha-amino acids, but changing their respective positions in the peptide chain; (b) using different C-terminal alpha,alpha-disubstituted alpha-amino acids in the peptide chain; (c) using different beta-hydroxy acids; and (d) using different diastereoisomers of the 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:2001
Deposited On:23 Oct 2013 06:34
Last Modified:07 Dec 2017 23:01
Publisher:Elsevier
ISSN:0040-4020
Publisher DOI:https://doi.org/10.1016/S0040-4020(01)00091-6

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