UZH-Logo

Maintenance Infos

3-(Dimethylamino)-2,2-dimethyl-2H-azirin als Aib-Äquivalent: Synthese von Aib-Oligopeptiden


Obrecht, Daniel; Heimgartner, Heinz (1987). 3-(Dimethylamino)-2,2-dimethyl-2H-azirin als Aib-Äquivalent: Synthese von Aib-Oligopeptiden. Helvetica Chimica Acta, 70:102-115.

Abstract

3-(Dimethylamino)-2,2-dimethyl-2H-azirine (1) reacts with carboxylic acids at 0-25° to give 2-acylamino-N,N,2-trimethylpropionamides (= 2-acylamino-N,N-dimethylisobutyramide, acyl-Aib-NMe2) in excellent yields (Scheme 2 and 3). Examples of alpha-amino-, alpha-hydroxy-, and alpha-mercapto-carboxylic acids are given. On treatment with HCI in toluene, the terminal dimethylamide group is selectively converted to the corresponding carboxylic acid (acyl-Aib) via an amide cleavage (Scheme 4 and 5); 1,3-oxazol-5(4H)-ones are intermediates of this amide hydrolysis. This reaction sequence has been used for the extension of peptide chains (Scheme 6). The synthesis of Aib-oligopeptides using this methodology is described (Scheme 8).

3-(Dimethylamino)-2,2-dimethyl-2H-azirine (1) reacts with carboxylic acids at 0-25° to give 2-acylamino-N,N,2-trimethylpropionamides (= 2-acylamino-N,N-dimethylisobutyramide, acyl-Aib-NMe2) in excellent yields (Scheme 2 and 3). Examples of alpha-amino-, alpha-hydroxy-, and alpha-mercapto-carboxylic acids are given. On treatment with HCI in toluene, the terminal dimethylamide group is selectively converted to the corresponding carboxylic acid (acyl-Aib) via an amide cleavage (Scheme 4 and 5); 1,3-oxazol-5(4H)-ones are intermediates of this amide hydrolysis. This reaction sequence has been used for the extension of peptide chains (Scheme 6). The synthesis of Aib-oligopeptides using this methodology is described (Scheme 8).

Downloads

0 downloads since deposited on 21 May 2014
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:German
Date:1987
Deposited On:21 May 2014 14:45
Last Modified:05 Apr 2016 17:52
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel, Prof.-Hans-E.-Schmid-Stiftung
Permanent URL: https://doi.org/10.5167/uzh-95995

Download

[img]
Content: Published Version
Language: German
Filetype: PDF - Registered users only
Size: 984kB

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