TY - JOUR AU - Tanács, Dániel AU - Berkecz, Róbert AU - Bozsó, Zsolt AU - Tóth, Gábor K. AU - Armstrong, Daniel W. AU - Péter, Antal AU - Ilisz, István TI - Liquid Chromatographic Enantioseparation of Newly Synthesized Fluorinated Tryptophan Analogs Applying Macrocyclic Glycopeptides-Based Chiral Stationary Phases Utilizing Core-Shell Particles JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 25 PY - 2024 IS - 9 SP - 4719 SN - 1661-6596 DO - 10.3390/ijms25094719 UR - https://m2.mtmt.hu/api/publication/34830921 ID - 34830921 AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Németi, Gábor AU - Berkecz, Róbert AU - Le Minh, Tam AU - Szakonyi, Zsolt AU - Péter, Antal AU - Ilisz, István TI - High-performance liquid chromatographic enantioseparation of azole analogs of monoterpene lactones and amides focusing on the separation characteristics of polysaccharide-based chiral stationary phases JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1717 PY - 2024 PG - 9 SN - 0021-9673 DO - 10.1016/j.chroma.2024.464660 UR - https://m2.mtmt.hu/api/publication/34535772 ID - 34535772 N1 - Institute of Pharmaceutical Analysis, Interdisciplinary Excellence Centre, University of Szeged, Somogyi u. 4, Szeged, H-6720, Hungary Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Export Date: 5 February 2024 CODEN: JCRAE Correspondence Address: Ilisz, I.; Institute of Pharmaceutical Analysis, Somogyi u. 4, Hungary; email: ilisz.istvan@szte.hu Funding details: 6752 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding details: Innovációs és Technológiai Minisztérium Funding details: National Research, Development and Innovation Office, K137607, TKP2021-EGA-32 Funding text 1: This work was supported by the National Research, Development and Innovation Office-NKFIA through project K137607. Project no. TKP2021-EGA-32 has been implemented with the support provided by the Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund, financed under the TKP2021-EGA funding scheme. This work was supported by the ÚNKP-21-4 New National Excellence Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund. The publication was funded by the University of Szeged Open Access Fund (No. 6752). LA - English DB - MTMT ER - TY - CHAP AU - Németi, Gábor AU - Dániel, Ozsvár AU - Berkecz, Róbert AU - Péter, Antal AU - Wolfgang, Lindner AU - Ilisz, István ED - Tünde, Alapi ED - Berkecz, Róbert ED - Ilisz, István TI - Enantioselective separation of substituted amino acids utilizing cinchona alkaloid-based chiral stationary phases T2 - Proceedings of the 29th International Symposium on Analytical and Environmental Problems PB - University of Szeged CY - Szeged SN - 9789633069639 PY - 2023 SP - 42 EP - 42 PG - 1 UR - https://m2.mtmt.hu/api/publication/34391565 ID - 34391565 LA - English DB - MTMT ER - TY - GEN AU - Ilisz, István AU - G., Németi AU - Berkecz, Róbert AU - T.M., Le AU - Z., Szakonyi AU - Péter, Antal TI - HPLC study of the separation characteristics of polysaccharide-based chiral stationary phases with particular emphasis on the hysteretic behavior PY - 2023 PG - 1 UR - https://m2.mtmt.hu/api/publication/34386896 ID - 34386896 LA - English DB - MTMT ER - TY - GEN AU - Péter, Antal AU - D., Tanács AU - Berkecz, Róbert AU - D.W., Armstrong AU - Ilisz, István TI - Characteristics of chiral stationary phases utilizing superficially porous silica particles for the HPLC enantioseparation of unusual amino acid analogs PY - 2023 SP - P-CHIR05 PG - 1 UR - https://m2.mtmt.hu/api/publication/34386802 ID - 34386802 LA - English DB - MTMT ER - TY - BOOK AU - Németi, Gábor AU - Dániel, Ozsvár AU - Berkecz, Róbert AU - Péter, Antal AU - Wolfgang, Lindner AU - Ilisz, István TI - HPLC Study of the Enantioselective separation of β-methyl-substituted amino acids applying ion exchanger-based chiral stationary phases PY - 2023 SP - 1 UR - https://m2.mtmt.hu/api/publication/34380012 ID - 34380012 LA - English DB - MTMT ER - TY - BOOK AU - Ilisz, István AU - Péter, Antal AU - Körmöczi, Tímea AU - Berkecz, Róbert TI - Advanced analytical tools in pharmaceutical analysis. 1D and 2D LC-MS techniques applied in biomedical sciences. RDPA 2023 Recent Development in Pharmaceutical Analysis TS - RDPA 2023 Recent Development in Pharmaceutical Analysis PY - 2023 SP - 1 UR - https://m2.mtmt.hu/api/publication/34139065 ID - 34139065 LA - English DB - MTMT ER - TY - JOUR AU - Tanács, Dániel AU - Berkecz, Róbert AU - Armstrong, Daniel W. AU - Péter, Antal AU - Ilisz, István TI - 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 JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1697 PY - 2023 PG - 11 SN - 0021-9673 DO - 10.1016/j.chroma.2023.463997 UR - https://m2.mtmt.hu/api/publication/33761942 ID - 33761942 LA - English DB - MTMT ER - TY - CHAP AU - Ilisz, István AU - Németi, Gábor AU - Tanács, Dániel AU - Bajtai, Attila AU - Berkecz, Róbert AU - Péter, Antal ED - Felinger, Attila TI - Enantiomeric Separations Based on High-Performance Liquid Chromatography Utilizing Different Types of Chiral Stationary Phases T2 - 33rd International Symposium on Chromatography – ISC 2022 PB - Hungarian Society for Separation Sciences CY - Budapest SN - 9786155270741 PY - 2022 PG - 1 UR - https://m2.mtmt.hu/api/publication/33551507 ID - 33551507 LA - English DB - MTMT ER - TY - CHAP AU - Németi, Gábor AU - Le Minh, Tam AU - Szakonyi, Zsolt AU - Péter, Antal AU - Ilisz, István ED - Felinger, Attila TI - High-Performance Liquid Chromatographic Separations in Polar Organic and Normal Phase Mode Utilizing Polysaccharide-based Chiral Stationary Phases T2 - 33rd International Symposium on Chromatography – ISC 2022 PB - Hungarian Society for Separation Sciences CY - Budapest SN - 9786155270741 PY - 2022 PG - 1 UR - https://m2.mtmt.hu/api/publication/33551500 ID - 33551500 LA - English DB - MTMT ER -