UZH-Logo

Maintenance Infos

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.

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.

Citations

37 citations in Web of Science®
41 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 23 Oct 2013
0 downloads since 12 months
Detailed statistics

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:05 Apr 2016 17:03
Publisher:Elsevier
ISSN:0040-4020
Publisher DOI:https://doi.org/10.1016/S0040-4020(01)00091-6
Permanent URL: https://doi.org/10.5167/uzh-82091

Download

[img]
Content: Published Version
Filetype: PDF - Registered users only
Size: 268kB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations