Header

UZH-Logo

Maintenance Infos

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.

Statistics

Citations

Dimensions.ai Metrics

Altmetrics

Downloads

32 downloads since deposited on 12 Mar 2015
7 downloads since 12 months
Detailed statistics

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:14 Feb 2018 08:58
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche AG, Basel
OA Status:Green
Publisher DOI:https://doi.org/10.1002/hlca.201400359

Download

Download PDF  'Synthesis of Cyclopentapeptides with Three to Five Aib Units'.
Preview
Content: Accepted Version
Filetype: PDF
Size: 269kB