Cyclopropyl-containing sulfonyl amino acids: Exploring the enantioseparation through chiral ligand-exchange chromatography
- Autores: Sardella R.1, Ianni F.1, Pucciarini L.1, Marinozzi M.1, Zlotskii S.2, Natalini B.1
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Afiliações:
- University of Perugia, Department of Pharmaceutical Sciences
- Ufa State Petroleum Technological University
- Edição: Volume 87, Nº 5 (2017)
- Páginas: 1079-1084
- Seção: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/220018
- DOI: https://doi.org/10.1134/S1070363217050309
- ID: 220018
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Resumo
In the scope of a broader study focused on glutamate receptors regulators, we have been engaged in synthesis, analysis and pharmacological characterization of rigid analogues of glutamic acid. These compounds exhibited the bioisosteric replacement of the distal carboxylic group with the sulfonic one. Besides the sophisticated synthetic approach, we targeted preparation of a series of cyclopropyl-containing sulfonyl amino acids and development of a chromatographic enantioselective method suitable for distinguishing and quantifying the resulting isomers. Due to chelating ability, the chiral ligand-exchange chromatography (CLEC) was used for diastereo- and enantioseparation of the synthesized compounds. The CLEC-based enantioseparation was achieved by using a chiral mobile phase (CMP) system with N,N-dimethyl-(S)-phenylalanine [(S)-DMP] as the chiral selector. Only one of the investigated enantiomeric pairs was undiscriminated with the employed CLEC–CMP system which, very importantly, produced the simultaneous diastereo- and enantioseparation of two compounds of the series. Furthermore, the large α and RS values computed for three enantiomer pairs could be a good basis for a successful scale-up to a semi-preparative level.
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Sobre autores
R. Sardella
University of Perugia, Department of Pharmaceutical Sciences
Email: benedetto.natalini@unipg.it
Itália, Via del Liceo 1, Perugia, 06123
F. Ianni
University of Perugia, Department of Pharmaceutical Sciences
Email: benedetto.natalini@unipg.it
Itália, Via del Liceo 1, Perugia, 06123
L. Pucciarini
University of Perugia, Department of Pharmaceutical Sciences
Email: benedetto.natalini@unipg.it
Itália, Via del Liceo 1, Perugia, 06123
M. Marinozzi
University of Perugia, Department of Pharmaceutical Sciences
Email: benedetto.natalini@unipg.it
Itália, Via del Liceo 1, Perugia, 06123
S. Zlotskii
Ufa State Petroleum Technological University
Email: benedetto.natalini@unipg.it
Rússia, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062
B. Natalini
University of Perugia, Department of Pharmaceutical Sciences
Autor responsável pela correspondência
Email: benedetto.natalini@unipg.it
Itália, Via del Liceo 1, Perugia, 06123