Synthesis and Conformational Analysis of Pentapeptides Containing Enantiomerically Pure 2,2‐Disubstituted Glycines |
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Authors: | Kathrin A Brun Anthony Linden Heinz Heimgartner |
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Institution: | 1. Organisch‐chemisches Institut der Universit?t Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, (phone +41?44?635?42?82;2. fax: +41?44?635?68 12);3. Part of the Ph.D. thesis and the Diploma thesis of K. B., Universit?t Zürich. |
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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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Keywords: | Peptides Azirine/oxazolone method 2H‐Azirin‐3‐amines X‐Ray crystallography Peptaibols |
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