Header

UZH-Logo

Maintenance Infos

Synthesis of cyclic depsipeptides and peptides via direct amide cyclization


Villalgordo, Jose M; Heimgartner, Heinz (1997). Synthesis of cyclic depsipeptides and peptides via direct amide cyclization. Helvetica Chimica Acta, 80:748-766.

Abstract

The 2,2-disubstituted 2H-azirin-3-amines 7 (2,2-disubstituted 3-amino-2H-azirines) were used as amino-acid synthons in the preparation of medium-sized cyclic depsipeptides and peptides derived from salicylic acids 6 and anthranilic acid 19, respectively (Schemes2-4 and 5, resp.). The combination of the ‘azirine/oxazolone method’ for the synthesis of linear peptides containing alpha,alpha-disubstituted alpha-amino acids and the acid-catalyzed amide cyclization in DMF at 60” proved to be an excellent preparative route to ten-membered cyclic depsipeptides and peptides. In the case of the anthranilic-acid derivative, a transannular ring-closure reaction was observed (24 to 25). Larger rings proved to be extremely sensitive to hydrolysis.

Abstract

The 2,2-disubstituted 2H-azirin-3-amines 7 (2,2-disubstituted 3-amino-2H-azirines) were used as amino-acid synthons in the preparation of medium-sized cyclic depsipeptides and peptides derived from salicylic acids 6 and anthranilic acid 19, respectively (Schemes2-4 and 5, resp.). The combination of the ‘azirine/oxazolone method’ for the synthesis of linear peptides containing alpha,alpha-disubstituted alpha-amino acids and the acid-catalyzed amide cyclization in DMF at 60” proved to be an excellent preparative route to ten-membered cyclic depsipeptides and peptides. In the case of the anthranilic-acid derivative, a transannular ring-closure reaction was observed (24 to 25). Larger rings proved to be extremely sensitive to hydrolysis.

Statistics

Citations

30 citations in Web of Science®
29 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

0 downloads since deposited on 18 Nov 2013
0 downloads since 12 months

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:1997
Deposited On:18 Nov 2013 09:58
Last Modified:07 Dec 2017 23:46
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Prof. Dr. Hans E. Schmid-Stiftung
Publisher DOI:https://doi.org/10.1002/hlca.19970800312

Download