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Triazolopeptides: chirospecific synthesis and cis/trans prolyl ratios of structural isomers
Authors:Andreas Paul
Institution:Department of Medicinal Chemistry, Emil Fischer Center, Friedrich Alexander University, Schuhstraße 19, D-91052 Erlangen, Germany
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.
Keywords:Triazolopeptide  cis/trans Prolyl isomerization  Click chemistry  Azide-alkyne cycloaddition
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