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Synthesis of Z-Protected Aib- and Phe(2Me)-Containing Pentapeptides and Their Crystal Structures


Arnhold, Franziska S; Linden, Anthony; Heimgartner, Heinz (2014). Synthesis of Z-Protected Aib- and Phe(2Me)-Containing Pentapeptides and Their Crystal Structures. Helvetica Chimica Acta, 97(5):619-645.

Abstract

A series of pentapeptide derivatives containing alpha,alpha-disubstituted alpha-amino acids have been prepared by a combination of the 'azirine/oxazolone method' and segment condensations. X-Ray crystal-structure determinations of the molecular structures confirmed the presence of helical conformations stabilized by beta-turns of type III or III’. Pentapeptides containing (R)-Phe(2Me) form a right-handed helix, whereas those containing (S)-Phe(2Me) adopt a left-handed helical structure.

Abstract

A series of pentapeptide derivatives containing alpha,alpha-disubstituted alpha-amino acids have been prepared by a combination of the 'azirine/oxazolone method' and segment condensations. X-Ray crystal-structure determinations of the molecular structures confirmed the presence of helical conformations stabilized by beta-turns of type III or III’. Pentapeptides containing (R)-Phe(2Me) form a right-handed helix, whereas those containing (S)-Phe(2Me) adopt a left-handed helical structure.

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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:2014
Deposited On:21 May 2014 14:49
Last Modified:05 Apr 2016 17:52
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.201400084

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