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1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics
Date
2018-01-19
Author
Kracker, Oliver
Gora, Jerzy
Krzciuk-Gula, Joanna
Marıon, Antoıne
Neumann, Beate
Stammler, Hans-Georg
Niess, Anke
Antes, Iris
Latajka, Rafal
Sewald, Norbert
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Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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Peptidotriazolamers are hybrid foldamers combining features of peptides and triazolamers-repetitive peptidomimetic structures with triazoles replacing peptide bonds. We report on the synthesis of a new class of peptidomimetics, containing 1,5-disubstituted 1,2,3-triazoles in an alternating fashion with amide bonds and the analysis of their conformation in solid state and solution. Homo-or heterochiral peptidotriazolamers were obtained from enantiomerically pure propargylamines with stereogenic centers in the prop-argylic position and alpha-azido esters by ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) under microwave conditions in high yields. With such building blocks the peptidotriazolamers are readily available by solution phase synthesis. While the conformation of the homochiral peptidotriazolamer Boc-Ala[5Tz] Phe-Val[5Tz] Ala-Leu[5Tz] Val-OBzl resembles that of a beta VIa1 turn, the heterochiral peptidotriazolamer Boc- D-Ala[5Tz] Phe-D-Val[5Tz] Ala-d-Leu[5Tz] Val-OBzl adopts a polyproline-like repetitive structure.
Subject Keywords
Triazoles
,
Ruthenium
,
Peptidomimetics
,
Foldamers
,
Conformational analysis
URI
https://hdl.handle.net/11511/41914
Journal
CHEMISTRY-A EUROPEAN JOURNAL
DOI
https://doi.org/10.1002/chem.201704583
Collections
Department of Chemistry, Article
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O. Kracker et al., “1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics,”
CHEMISTRY-A EUROPEAN JOURNAL
, pp. 953–961, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41914.