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From 3-Amino-2H-azirines to Peptides


Heimgartner, Heinz (1998). From 3-Amino-2H-azirines to Peptides. In: Slovenski kemijski dnevi, Maribor, Slovenia, 17 September 1998 - 18 September 1998, 1-12.

Abstract

Easily available 3-amino-2H-azirines proved to be useful synthons in peptide chemistry. The smooth coupling with acids together with the selective hydrolysis of the C-terminal amide group present a novel strategy for the synthesis of peptides containing 2,2-disubstituted glycines ('Azirine/Oxazolone Method'). As a result of the gem-disubstitution, these conformationally restricted peptides preferentially form turns and helical structures. The scope of this methodology for the synthesis of linear and cyclic peptides is demonstrated by the preparation of poly-Aib-peptides, segments of peptaibols, and cyclopeptides. A variation of the 'Azirine/Oxazolone Method', using thiocarboxylic acids in the reaction with aminoazirines and a novel acid-catalyzed isomerization of the resulting thioamides, offers a convenient access to endothiopeptides. The specifically thionated products are of special interest as they contain two elements of conformational restriction.

Abstract

Easily available 3-amino-2H-azirines proved to be useful synthons in peptide chemistry. The smooth coupling with acids together with the selective hydrolysis of the C-terminal amide group present a novel strategy for the synthesis of peptides containing 2,2-disubstituted glycines ('Azirine/Oxazolone Method'). As a result of the gem-disubstitution, these conformationally restricted peptides preferentially form turns and helical structures. The scope of this methodology for the synthesis of linear and cyclic peptides is demonstrated by the preparation of poly-Aib-peptides, segments of peptaibols, and cyclopeptides. A variation of the 'Azirine/Oxazolone Method', using thiocarboxylic acids in the reaction with aminoazirines and a novel acid-catalyzed isomerization of the resulting thioamides, offers a convenient access to endothiopeptides. The specifically thionated products are of special interest as they contain two elements of conformational restriction.

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Additional indexing

Item Type:Conference or Workshop Item (Lecture), not_refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Event End Date:18 September 1998
Deposited On:12 Nov 2013 14:18
Last Modified:20 Feb 2018 08:08
OA Status:Closed

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