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Synthesis and conformational analysis of pentapeptides containing enantiomerically pure 2,2-disubstituted glycines


Brun, K A; Linden, A; Heimgartner, H (2008). Synthesis and conformational analysis of pentapeptides containing enantiomerically pure 2,2-disubstituted glycines. Helvetica Chimica Acta, 91(3):526-558.

Abstract

The synthesis and conformational analysis of model pentapeptides with the sequence Z-Leu-Aib-Xaa-Gln-Valol is described. These peptides contain two 2,2-disubstituted glycines (α,α-disubstituted α-amino acids), i.e., Aib (aminoisobutyric acid) and a series of unsymmetrically substituted, enantiomerically pure amino acids Xaa. These disubstituted amino acids were incorporated into the model peptides via the ‘azirine/oxazolone method’.
Conformational analysis was performed in solution by means of NMR techniques and in the solid state by X-ray crystallography. Both methods show that the backbones of thesemodel peptides form helical conformations, as is expected for 2,2-disubstitued glycinecontaining peptides.

Abstract

The synthesis and conformational analysis of model pentapeptides with the sequence Z-Leu-Aib-Xaa-Gln-Valol is described. These peptides contain two 2,2-disubstituted glycines (α,α-disubstituted α-amino acids), i.e., Aib (aminoisobutyric acid) and a series of unsymmetrically substituted, enantiomerically pure amino acids Xaa. These disubstituted amino acids were incorporated into the model peptides via the ‘azirine/oxazolone method’.
Conformational analysis was performed in solution by means of NMR techniques and in the solid state by X-ray crystallography. Both methods show that the backbones of thesemodel peptides form helical conformations, as is expected for 2,2-disubstitued glycinecontaining peptides.

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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:2008
Deposited On:06 Feb 2009 08:03
Last Modified:05 Apr 2016 12:57
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.200890057

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