Brunner, Henri and Tsuno, Takashi and Balazs, Gabor (2021) A Chirality Chain in Phenylglycine, Phenylpropionic Acid, and Ibuprofen. SYMMETRY-BASEL, 13 (1): 55. ISSN 2073-8994
Full text not available from this repository. (Request a copy)Abstract
Our strategy to analyze the structures of natural amino acids with respect to the interaction of three different elements of chirality within the molecules was applied to the non-natural amino acid (S)-alpha-phenylglycine, its analogue (S)-alpha-phenylpropionic acid, and the drug (S)-ibuprofen. The three chirality elements are the configuration at C-alpha, the conformation at the C-alpha-C' bond, and the distortion of the planar carboxylic group to a flat asymmetric tetrahedron. In all three compounds, a given (S) configuration at C-alpha predominantly induces (M) conformation at the C-alpha-C' bond, which in turn preferentially distorts the carboxylic group to a tetrahedron with (R) configuration. Both steps of this chirality chain display high selectivities. Due to varying co-crystallization partners, in all the structures the molecules are in different environments with respect to packing and hydrogen bonding. Nevertheless, the structural pattern and the diaselectivities of the chirality chain persist. For phenylglycine, DFT (Density Functional Theory) calculations confirm the structural results.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | amino acids; α -phenylpropionic acid; ibuprofen; chirality; diastereoselectivity; analysis of CSD structures; X-ray structure determination |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 17 Aug 2022 12:04 |
| Last Modified: | 17 Aug 2022 12:04 |
| URI: | https://pred.uni-regensburg.de/id/eprint/46642 |
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