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Synthesis and Conformational Analysis of Pentapeptides Containing Enantiomerically Pure 2,2-Disubstituted Glycines

✍ Scribed by Kathrin A. Brun; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
481 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 these model peptides adopt helical conformations, as expected for 2,2‐disubstitued glycine‐containing peptides.

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