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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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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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.
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CHEMISTRY-A EUROPEAN JOURNAL
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24
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4
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953-961
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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. doi:10.1002/chem.201704583
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.

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