1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics

2018-01-19
Kracker, Oliver
Gora, Jerzy
Krzciuk-Gula, Joanna
Marıon, Antoıne
Neumann, Beate
Stammler, Hans-Georg
Niess, Anke
Antes, Iris
Latajka, Rafal
Sewald, Norbert
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.
CHEMISTRY-A EUROPEAN JOURNAL

Suggestions

1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties
Schroeder, David C.; Kracker, Oliver; Froehr, Tanja; Gora, Jerzy; Jewginski, Michal; Niess, Anke; Antes, Iris; Latajka, Rafal; Marıon, Antoıne; Sewald, Norbert (Frontiers Media SA, 2019-03-26)
Peptidotriazolamers are hybrid foldamers with features of peptides and triazolamers, containing alternation of amide bonds and 1,4-dlsubstltuted 1H-1,2,3-triazoles with conservation of the amino acid side chains. We report on the synthesis of a new class of peptidomimetics, containing 1,4-disubstituted 1H-1,2,3-triazoles in alternation with amide bonds and the elucidation of their conformational properties in solution. Based on enantiomerically pure propargylamines bearing the stereogenic center in the prop...
Synthesis of new mediators for electrochemical nad/nadh recycling
Khalily, Mohammad Aref; Demir, Ayhan Sıtkı; Department of Chemistry (2011)
The synthesis of enantiopure compounds can be achieved by using dehydrogenases as biocatalysts. For instance, reduction reactions of prochiral compounds (ketones, aldehydes and nitriles) into chiral compounds can be achieved by dehydrogenases. These dehydrogenases are cofactor dependent where cofactor is Nicotinamide Adenin Dinucleotite having some restrictions that confines usage of dehydrogenases in organic synthesis including instability of cofactor in water and high cost. Therefore, suitable recycling m...
Ni-MCM-41 type mesoporous catalysts synthesized by one-pot hydrothermal procedure for steam reforming of ethanol
Ozdogan, Ekin; Doğu, Timur; DOĞU, GÜLŞEN (2007-01-02)
In the present study, Ni incorporated MCM-41 structured mesoporous catalysts with a Ni/Si atomic ratio of 0.036 and 0.15 were prepared by a direct hydrothermal synthesis procedure. These catalysts had surface area values of 860.5 m(2)/g (Ni-MCM-41 having a Ni/Si ratio of 0.036) and 944.9 m(2)/g (Ni-MCM-41 having a Ni/Si ratio of 0.15). They also had narrow pore size distributions with average pore diameters of 2.7-2.6 nm respectively. Ni MCM-41 synthesized by the one-pot hydrothermal synthesis procedure sho...
CCL- and PLE-catalyzed reverse enantiomeric separation of various (+/-)-2-thienylcarbinols
Tanyeli, Cihangir; Ozdemirhan, D (2001-01-01)
(+/-)-2-Thienylcarbinols and their O-acetyl derivatives were resolved in reverse separation by CCL and PLE catalysed hydrolysis to afford optically active 2-thienylcarbinols in 35%-99% e.e. that are valuable chiral building blocks, in particular in the synthesis of pheromones and some alkoloid type natural products. Absolute configurations were determined by the correlation of specific rotation values with the literature and by transforming into the corresponding secondary alcohols via reductive desulfuriza...
PFAM catalyzed enantioselective diethylzinc addition to imines
Doğan, Özdemir (2015-01-01)
Chiral amines are important starting materials for the synthesis of biologically important compounds. Enantioselective addition of dialkylzinc reagents to imines is a reliable method for the synthesis of these compounds. Different chiral catalysts were developed and used for this method. Phosphorous based PFAM catalysts were tried for the first time in the enantioselective synthesis of amines by reacting diethylzinc with N-sulfonyl imines and N-diphenylphosphinoyl imines. Chiral amines were isolated with mo...
Citation Formats
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.