Helical Oligomers of Thiazole-Based γ-Amino Acids: Synthesis and Structural Studies

Helical Oligomers of Thiazole-Based γ-Amino Acids: Synthesis and Structural Studies

9‐Helix: 4‐Amino(methyl)‐1,3‐thiazole‐5‐carboxylic acids (ATCs) were synthesized as new γ‐amino acid building blocks. The structures of various ATC oligomers were analyzed in solution by CD and NMR spectroscopy and in the solid state by X‐ray crystallography. The ATC sequences adopted a well‐defined...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-06, Vol.52 (23), p.6006-6010
Hauptverfasser: Mathieu, Loïc, Legrand, Baptiste, Deng, Cheng, Vezenkov, Lubomir, Wenger, Emmanuel, Didierjean, Claude, Amblard, Muriel, Averlant-Petit, Marie-Christine, Masurier, Nicolas, Lisowski, Vincent, Martinez, Jean, Maillard, Ludovic T.
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemistry
Circular Dichroism
conformation analysis
foldamers
helical structures
Models, Molecular
peptidomimetics
Polymers - chemistry
Thiazoles - chemical synthesis
Thiazoles - chemistry
γ-peptides
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Zusammenfassung:9‐Helix: 4‐Amino(methyl)‐1,3‐thiazole‐5‐carboxylic acids (ATCs) were synthesized as new γ‐amino acid building blocks. The structures of various ATC oligomers were analyzed in solution by CD and NMR spectroscopy and in the solid state by X‐ray crystallography. The ATC sequences adopted a well‐defined 9‐helix structure in the solid state and in aprotic and protic organic solvents as well as in aqueous solution.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201302106