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Synthesis of Cyclopentapeptides with Three to Five Aib Units


Arnhold, Franziska S; Linden, Anthony; Heimgartner, Heinz (2015). Synthesis of Cyclopentapeptides with Three to Five Aib Units. Helvetica Chimica Acta, 98(2):232-244.

Abstract

Four new Aib-containing cyclopentapeptides have been synthesized by cyclization of the corresponding linear pentapeptides using the diethyl phosphorocyanidate (DEPC)/EtN(iPr)2 method. The linear precursors were prepared via the 'azirine/oxazolone method', i.e., the Aib units were introduced by the reaction of amino acids or peptide acids with a 2,2-dimethyl-2H-azirin-3-amine, followed by selective hydrolysis of the terminal amide function. Most remarkably, cyclo[(Aib)5] exists in CDCl3 solution in a symmetrical conformation, i.e., no intramolecular H-bonds are detectable.

Abstract

Four new Aib-containing cyclopentapeptides have been synthesized by cyclization of the corresponding linear pentapeptides using the diethyl phosphorocyanidate (DEPC)/EtN(iPr)2 method. The linear precursors were prepared via the 'azirine/oxazolone method', i.e., the Aib units were introduced by the reaction of amino acids or peptide acids with a 2,2-dimethyl-2H-azirin-3-amine, followed by selective hydrolysis of the terminal amide function. Most remarkably, cyclo[(Aib)5] exists in CDCl3 solution in a symmetrical conformation, i.e., no intramolecular H-bonds are detectable.

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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:English
Date:February 2015
Deposited On:12 Mar 2015 10:26
Last Modified:05 Apr 2016 19:07
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.201400359

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