@article{MTMT:34830921, title = {Liquid Chromatographic Enantioseparation of Newly Synthesized Fluorinated Tryptophan Analogs Applying Macrocyclic Glycopeptides-Based Chiral Stationary Phases Utilizing Core-Shell Particles}, url = {https://m2.mtmt.hu/api/publication/34830921}, author = {Tanács, Dániel and Berkecz, Róbert and Bozsó, Zsolt and Tóth, Gábor K. and Armstrong, Daniel W. and Péter, Antal and Ilisz, István}, doi = {10.3390/ijms25094719}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {25}, unique-id = {34830921}, issn = {1661-6596}, abstract = {Due to the favorable features obtained through the incorporation of fluorine atom(s), fluorinated drugs are a group with emerging pharmaceutical importance. As their commercial availability is still very limited, to expand the range of possible candidates, new fluorinated tryptophan analogs were synthesized. Control of enantiopurity during the synthesis procedure requires that highly efficient enantioseparation methods be available. In this work, the enantioseparation of seven fluorinated tryptophans and tryptophan was studied and compared systematically to (i) develop analytical methods for enantioselective separations and (ii) explore the chromatographic features of the fluorotrytophans. For enantioresolution, macrocyclic glycopeptide-based selectors linked to core-shell particles were utilized, applying liquid chromatography-based methods. Application of the polar-ionic mode resulted in asymmetric and broadened peaks, while reversed-phase conditions, together with mobile-phase additives, resulted in baseline separation for all studied fluorinated tryptophans. The marked differences observed between the methanol and acetonitrile-containing eluent systems can be explained by the different solvation abilities of the bulk solvents of the applied mobile phases. Among the studied chiral selectors, teicoplanin and teicoplanin aglycone were found to work effectively. Under optimized conditions, baseline separations were achieved within 6 min. Ionic interactions were semi-quantitatively characterized and found to not influence enantiorecognition. Interestingly, fluorination of the analytes does not lead to marked changes in the chromatographic characteristics of the methanol-containing eluents, while larger differences were noticed when the polar but aprotic acetonitrile was applied. Experiments conducted on the influence of the separation temperature indicated that the separations are enthalpically driven, with only one exception. Enantiomeric elution order was found to be constant on both teicoplanin and teicoplanin aglycone-based chiral stationary phases (L < D) under all applied chromatographic conditions.}, year = {2024}, eissn = {1422-0067}, pages = {4719}, orcid-numbers = {Tanács, Dániel/0000-0003-1011-8638; Berkecz, Róbert/0000-0002-9076-2177; Bozsó, Zsolt/0000-0002-5713-3096; Armstrong, Daniel W./0000-0003-0501-6231; Ilisz, István/0000-0001-8282-457X} } @article{MTMT:34535772, title = {High-performance liquid chromatographic enantioseparation of azole analogs of monoterpene lactones and amides focusing on the separation characteristics of polysaccharide-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/34535772}, author = {Németi, Gábor and Berkecz, Róbert and Le Minh, Tam and Szakonyi, Zsolt and Péter, Antal and Ilisz, István}, doi = {10.1016/j.chroma.2024.464660}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1717}, unique-id = {34535772}, issn = {0021-9673}, year = {2024}, eissn = {1873-3778}, orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Berkecz, Róbert/0000-0002-9076-2177; Le Minh, Tam/0000-0002-8296-887X; Szakonyi, Zsolt/0000-0003-2432-8409; Ilisz, István/0000-0001-8282-457X} } @{MTMT:34391565, title = {Enantioselective separation of substituted amino acids utilizing cinchona alkaloid-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/34391565}, author = {Németi, Gábor and Dániel, Ozsvár and Berkecz, Róbert and Péter, Antal and Wolfgang, Lindner and Ilisz, István}, booktitle = {Proceedings of the 29th International Symposium on Analytical and Environmental Problems}, unique-id = {34391565}, year = {2023}, pages = {42-42}, orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X} } @misc{MTMT:34386896, title = {HPLC study of the separation characteristics of polysaccharide-based chiral stationary phases with particular emphasis on the hysteretic behavior}, url = {https://m2.mtmt.hu/api/publication/34386896}, author = {Ilisz, István and G., Németi and Berkecz, Róbert and T.M., Le and Z., Szakonyi and Péter, Antal}, unique-id = {34386896}, year = {2023}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Berkecz, Róbert/0000-0002-9076-2177} } @misc{MTMT:34386802, title = {Characteristics of chiral stationary phases utilizing superficially porous silica particles for the HPLC enantioseparation of unusual amino acid analogs}, url = {https://m2.mtmt.hu/api/publication/34386802}, author = {Péter, Antal and D., Tanács and Berkecz, Róbert and D.W., Armstrong and Ilisz, István}, unique-id = {34386802}, year = {2023}, pages = {P-CHIR05}, orcid-numbers = {Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X} } @misc{MTMT:34380012, title = {HPLC Study of the Enantioselective separation of β-methyl-substituted amino acids applying ion exchanger-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/34380012}, author = {Németi, Gábor and Dániel, Ozsvár and Berkecz, Róbert and Péter, Antal and Wolfgang, Lindner and Ilisz, István}, unique-id = {34380012}, year = {2023}, orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X} } @misc{MTMT:34139065, title = {Advanced analytical tools in pharmaceutical analysis. 1D and 2D LC-MS techniques applied in biomedical sciences. RDPA 2023 Recent Development in Pharmaceutical Analysis}, url = {https://m2.mtmt.hu/api/publication/34139065}, author = {Ilisz, István and Péter, Antal and Körmöczi, Tímea and Berkecz, Róbert}, unique-id = {34139065}, year = {2023}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Körmöczi, Tímea/0000-0002-0973-2473; Berkecz, Róbert/0000-0002-9076-2177} } @article{MTMT:33761942, title = {Enantioseparation of α-substituted proline analogs with macrocyclic glycopeptide-based chiral stationary phases immobilized on superficially porous particles of silica applying liquid chromatography with ultraviolet and mass spectrometric detection}, url = {https://m2.mtmt.hu/api/publication/33761942}, author = {Tanács, Dániel and Berkecz, Róbert and Armstrong, Daniel W. and Péter, Antal and Ilisz, István}, doi = {10.1016/j.chroma.2023.463997}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1697}, unique-id = {33761942}, issn = {0021-9673}, year = {2023}, eissn = {1873-3778}, orcid-numbers = {Tanács, Dániel/0000-0003-1011-8638; Berkecz, Róbert/0000-0002-9076-2177; Armstrong, Daniel W./0000-0003-0501-6231; Ilisz, István/0000-0001-8282-457X} } @{MTMT:33551507, title = {Enantiomeric Separations Based on High-Performance Liquid Chromatography Utilizing Different Types of Chiral Stationary Phases}, url = {https://m2.mtmt.hu/api/publication/33551507}, author = {Ilisz, István and Németi, Gábor and Tanács, Dániel and Bajtai, Attila and Berkecz, Róbert and Péter, Antal}, booktitle = {33rd International Symposium on Chromatography – ISC 2022}, unique-id = {33551507}, year = {2022}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Németi, Gábor/0000-0001-7312-8353; Tanács, Dániel/0000-0003-1011-8638; Bajtai, Attila/0000-0002-8054-6526; Berkecz, Róbert/0000-0002-9076-2177} } @{MTMT:33551500, title = {High-Performance Liquid Chromatographic Separations in Polar Organic and Normal Phase Mode Utilizing Polysaccharide-based Chiral Stationary Phases}, url = {https://m2.mtmt.hu/api/publication/33551500}, author = {Németi, Gábor and Le Minh, Tam and Szakonyi, Zsolt and Péter, Antal and Ilisz, István}, booktitle = {33rd International Symposium on Chromatography – ISC 2022}, unique-id = {33551500}, year = {2022}, orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Le Minh, Tam/0000-0002-8296-887X; Szakonyi, Zsolt/0000-0003-2432-8409; Ilisz, István/0000-0001-8282-457X} }