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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).

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).

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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:German
Date:1987
Deposited On:21 May 2014 14:45
Last Modified:21 Nov 2017 17:21
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

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