A cyclic trimer of 2-(2-aminophenoxy)propionic acid with a bowl-shaped structure |
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Authors: | Motohiro Akazome Junpei Sukegawa Yohei Goto Shoji Matsumoto |
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Institution: | Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoicho, Inageku, Chiba 263-8522, Japan |
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Abstract: | A cyclic trimer of (R)-2-(2-aminophenoxy)propanoic acid, a δ-amino acid analogue, was synthesized. Molecular mechanics calculations on the cyclic trimer predicted that a concave network of sequential hydrogen bonds forms a C3-symmetric bowl-shaped structure. Evidence for this conformation was found in the NMR spectra of the trimer in d-chloroform. Although the single-crystal structure of the cyclic trimer indicates that chloroform could be included in the bowl-shaped structure, the conformation was not C3-symmetric and the hydrogen bonding network was of a different mode. These different conformations between solid and solution were reasonably clear from IR spectra. |
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Keywords: | Foldamers δ-Amino acid Bowl-shaped structure Hydrogen bonding |
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