1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics
Kracker O, Gora J, Krzciuk-Gula J, Marion A, Neumann B, Stammler H-G, Nieß A, Antes I, Latajka R, Sewald N (2018)
Chemistry - A European Journal 24(4): 953-961.
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Autor*in
Kracker, OliverUniBi;
Gora, JerzyUniBi;
Krzciuk-Gula, Joanna;
Marion, Antoine;
Neumann, BeateUniBi;
Stammler, Hans-GeorgUniBi;
Nieß, AnkeUniBi;
Antes, Iris;
Latajka, Rafal;
Sewald, NorbertUniBi 
Einrichtung
Abstract / Bemerkung
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.
Stichworte
conformational analysis;
foldamers;
peptidomimetics;
ruthenium;
triazoles
Erscheinungsjahr
2018
Zeitschriftentitel
Chemistry - A European Journal
Band
24
Ausgabe
4
Seite(n)
953-961
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2919079
Zitieren
Kracker O, Gora J, Krzciuk-Gula J, et al. 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal. 2018;24(4):953-961.
Kracker, O., Gora, J., Krzciuk-Gula, J., Marion, A., Neumann, B., Stammler, H. - G., Nieß, A., et al. (2018). 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal, 24(4), 953-961. https://doi.org/10.1002/chem.201704583
Kracker, Oliver, Gora, Jerzy, Krzciuk-Gula, Joanna, Marion, Antoine, Neumann, Beate, Stammler, Hans-Georg, Nieß, Anke, Antes, Iris, Latajka, Rafal, and Sewald, Norbert. 2018. “1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics”. Chemistry - A European Journal 24 (4): 953-961.
Kracker, O., Gora, J., Krzciuk-Gula, J., Marion, A., Neumann, B., Stammler, H. - G., Nieß, A., Antes, I., Latajka, R., and Sewald, N. (2018). 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal 24, 953-961.
Kracker, O., et al., 2018. 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal, 24(4), p 953-961.
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, vol. 24, 2018, pp. 953-961.
Kracker, O., Gora, J., Krzciuk-Gula, J., Marion, A., Neumann, B., Stammler, H.-G., Nieß, A., Antes, I., Latajka, R., Sewald, N.: 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal. 24, 953-961 (2018).
Kracker, Oliver, Gora, Jerzy, Krzciuk-Gula, Joanna, Marion, Antoine, Neumann, Beate, Stammler, Hans-Georg, Nieß, Anke, Antes, Iris, Latajka, Rafal, and Sewald, Norbert. “1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics”. Chemistry - A European Journal 24.4 (2018): 953-961.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
1 Zitation in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties.
Schröder DC, Kracker O, Fröhr T, Góra J, Jewginski M, Nieß A, Antes I, Latajka R, Marion A, Sewald N., Front Chem 7(), 2019
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Schröder DC, Kracker O, Fröhr T, Góra J, Jewginski M, Nieß A, Antes I, Latajka R, Marion A, Sewald N., Front Chem 7(), 2019
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