Triazolopeptides: chirospecific synthesis and cis/trans prolyl ratios of structural isomers |
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Authors: | Andreas Paul |
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Affiliation: | Department of Medicinal Chemistry, Emil Fischer Center, Friedrich Alexander University, Schuhstraße 19, D-91052 Erlangen, Germany |
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Abstract: | As cis/trans prolyl isomerization plays a crucial role in various biological processes, peptide mimics capable of modifying the cis/trans Xaa-Pro ratio are of particular interest. A practical approach toward proline derived triazolopeptides employing [3+2] azide-alkyne cycloadditions as the key reaction step and the analysis of their cis/trans prolyl ratios are reported. Structural investigations indicated the adjustability of both the cis-percentage and the conformational stability toward intramolecular H-bonding effects. |
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Keywords: | Triazolopeptide cis/trans Prolyl isomerization Click chemistry Azide-alkyne cycloaddition |
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