TY - JOUR AU - Wang, Xiang AU - Peng, Huanjun AU - Zhang, Zilong AU - Wu, Jiajia AU - Yu, Jiayu AU - Zeng, Hanlin AU - Yang, Hanqi AU - Zhou, Guangming AU - Peng, Jingdong TI - Graft copolymerization of anion and cation onto silica and application in mixed-mode of reversed phase/ hydrophilic interaction/ ion exchange chromatography JF - TALANTA J2 - TALANTA VL - 266 PY - 2024 PG - 9 SN - 0039-9140 DO - 10.1016/j.talanta.2023.125055 UR - https://m2.mtmt.hu/api/publication/34276053 ID - 34276053 AB - Ionic liquids (ILs) have turned out to be one of the best choices to fabricate mixed-mode stationary phases, this work aimed to investigate the possibility and merit of copolymerizing cations and anions as modifications. We prepared two ILs stationary phases, one of which was constructed by copolymerizing cation and anion (pvinylbenzene sulfonate). Two stationary phases were characterized and comprehensively evaluated. The stationary phases showed great repeatability (RSD <0.87%) and high efficiency (up to 83,810 plate/m). Both stationary phases can operate under a mixed mode of reversed phase/hydrophilic interaction/ion exchange chromatography (RPLC/HILIC/IEC). Chromatographic evaluation results revealed that copolymerized anions endow stationary phase superior selectivity under RPLC and HILIC modes, so hydrophobic terphenyls isomer (under ACN/H2O = 35/65) and hydrophilic nucleotides and bases (under ACN/100 mM NH(4)FA buffer = 90/10) are better separated. Organic and inorganic anions showed entirely different retention behaviors on two stationary phases, and the mechanism was investigated by linear solvation energy relationship (LSER) and thermodynamic analysis. This work proved that copolymerizing cations and anions of ILs could be a promising method to prepare stationary phases, the retention property and mechanism need further research. LA - English DB - MTMT ER - TY - JOUR AU - Tensi, Leonardo AU - Dall'Anese, Anna AU - Annunziata, Alfonso AU - Mearini, Simone AU - Nofrini, Vittorio AU - Rodriguez, Gabriel Menendez AU - Carotti, Andrea AU - Sardella, Roccaldo AU - Ruffo, Francesco AU - Macchioni, Alceo TI - Synthesis and Characterization of Chiral Iridium Complexes Bearing Carbohydrate Functionalized Pyridincarboxamide Ligands and Their Application as Catalysts in the Asymmetric Transfer Hydrogenation of ?-Ketoacids in Water JF - ORGANOMETALLICS J2 - ORGANOMETALLICS VL - 42 PY - 2023 IS - 2 SP - 157 EP - 166 PG - 10 SN - 0276-7333 DO - 10.1021/acs.organomet.2c00544 UR - https://m2.mtmt.hu/api/publication/33889157 ID - 33889157 AB - [Cp*IrLnCl] complexes [L1 = (methyl-beta-D-gluco-pyranosid-2-yl)picolinamide, 1; L2 = (methyl-3,4,6-tri-O-acetyl-beta- D-glucopyranosid-2-yl)picolinamide, 2; L3 = (2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosid-1-yl)picolinamide, 3] have been synthe-sized and completely characterized in solution, by 1D-and 2D-NMR spectroscopy, and in the solid state, by X-ray single crystal diffractometry. Despite the chirality of the Ln-moiety and metal, a single diastereoisomer is observed for L1 (1) and L2 (2) having a (R)-iridium configuration: the pyranose moiety is oriented in a way to minimize the interactions of the axial protons, vicinal to the amide moiety, and Cp*, with the OMe-group pointing toward the Cp*-ligand and away from Ir-Cl. Such a diastereoisomer is also favored by the establishment of an O-H center dot center dot center dot Cl-Ir hydrogen bond (2.356 angstrom) and by the minimization of the steric repulsion between one acetyl moiety of L2 and Cp* and picolinamide ligands in 1 and 2, respectively. DFT calculations computed a stabilization by more than 5.9 and 3.1 kcal/mol of this diastereoisomer with respect to other possible ones. Two interconverting diastereoisomers with different chirality at iridium are instead observed in solution for complex 3 in which-CH2OAc [3a, 63%, (R)] and -OAc [3b, 37%, (S)] moieties, respectively, are oriented toward Cp* and N-arm of picolinamide ligands. Consistently, DFT calculations indicate that 3a and 3b have a comparable stability (OLE = 1.2 kcal/mol). Complexes 1-3 catalyze the asymmetric transfer hydrogenation of RC(O)C(O)OH to RCH(OH)C(O)OH [R = Ph (PGA), CH2Ph (PPA), CH2(4-OH)C6H4 (HPPA)], using both HCOOH and H3PO3 as hydrogen donor, in water at pH 7 (by phosphate buffer), with excellent chemoselectivity and efficiency (conversion >99%) and moderate to good enantioselectivity (30- 70% ee). Utilizing catalyst 3 instead of 2, bearing the pseudoenantiomeric L3 of L2 ligand, causes a reduction of the percentage of the major enantiomer (R) with PGA and an inversion of stereoselectivity from (R) to (S) with PPA and HPPA substrates. LA - English DB - MTMT ER - TY - JOUR AU - Németi, Gábor AU - Berkecz, Róbert AU - Shahmohammadi, Sayeh AU - Forró, Enikő AU - Lindner, Wolfgang AU - Péter, Antal AU - Ilisz, István TI - Enantioselective high-performance liquid chromatographic separation of fluorinated ß- phenylalanine derivatives utilizing Cinchona alkaloid-based ion-exchanger chiral stationary phases. Enantioselective separation of fluorinated ß-phenylalanine derivatives TS - Enantioselective separation of fluorinated ß-phenylalanine derivatives JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1670 PY - 2022 PG - 10 SN - 0021-9673 DO - 10.1016/j.chroma.2022.462974 UR - https://m2.mtmt.hu/api/publication/32741660 ID - 32741660 N1 - Institute of Pharmaceutical Analysis, Interdisciplinary Excellence Centre, University of Szeged, H-6720 Szeged, Somogyi u. 4, Hungary Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Department of Analytical Chemistry, University of Vienna, Währinger Strasse 38, Vienna, 1090, Austria Cited By :1 Export Date: 21 June 2023 CODEN: JCRAE Correspondence Address: Ilisz, I.; Institute of Pharmaceutical Analysis, Somogyi B. u. 4, Hungary; email: ilisz.istvan@szte.hu Chemicals/CAS: acetonitrile, 75-05-8; methanol, 67-56-1; phenylalanine, 3617-44-5, 63-91-2; Cinchona Alkaloids; Methanol; Phenylalanine Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding details: Innovációs és Technológiai Minisztérium Funding details: National Research, Development and Innovation Office, K129049, K137607, TKP2021-EGA-32 Funding text 1: This work was supported by National Research, Development and Innovation Office-NKFIA through projects K137607 and K129049. 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. LA - English DB - MTMT ER - TY - JOUR AU - Tanács, Dániel AU - Berkecz, Róbert AU - Misicka, Aleksandra AU - Tymecka, Dagmara AU - Fülöp, Ferenc AU - Armstrong, Daniel W. AU - Ilisz, István AU - Péter, Antal TI - Enantioseparation of ß-amino acids by liquid chromatography using core-shell chiral stationary phases based on teicoplanin and teicoplanin aglycone JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1653 PY - 2021 PG - 14 SN - 0021-9673 DO - 10.1016/j.chroma.2021.462383 UR - https://m2.mtmt.hu/api/publication/32107146 ID - 32107146 LA - English DB - MTMT ER - TY - JOUR AU - Tanács, Dániel AU - Orosz, Tímea AU - Ilisz, István AU - Péter, Antal AU - Lindner, Wolfgang TI - Unexpected effects of mobile phase solvents and additives on retention and resolution of N-acyl-D,L-leucine applying Cinchonane-based chiral ion exchangers JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1648 PY - 2021 PG - 12 SN - 0021-9673 DO - 10.1016/j.chroma.2021.462212 UR - https://m2.mtmt.hu/api/publication/32008555 ID - 32008555 LA - English DB - MTMT ER - TY - JOUR AU - Varfaj, Ina AU - Protti, Michele AU - Di Michele, Alessandro AU - Macchioni, Alceo AU - Lindner, Wolfgang AU - Carotti, Andrea AU - Sardella, Roccaldo AU - Mercolini, Laura TI - Efficient enantioresolution of aromatic alpha-hydroxy acids with Cinchona alkaloid-based zwitterionic stationary phases and volatile polar-ionic eluents JF - ANALYTICA CHIMICA ACTA J2 - ANAL CHIM ACTA VL - 1180 PY - 2021 PG - 10 SN - 0003-2670 DO - 10.1016/j.aca.2021.338928 UR - https://m2.mtmt.hu/api/publication/32234964 ID - 32234964 AB - Single enantiomers of mandelic acid (1), 3-phenyllactic acid (2), and 3-(4-hydroxyphenyl)lactic acid (3) are the subject of many fields of investigation, spanning from the pharmaceutical synthesis to that of biocompatible and biodegradable polymers, while passing from the interest towards their antimicrobial activity to their role as biomarkers of particular pathological conditions or occupational exposures to specific xenobiotics. All above mentioned issues justify the need for accurate analytical methods enabling the correct determination of the individual enantiomers. So far, all the developed liquid chromatography (LC) methods were not or hardly compatible with mass spectrometry (MS) detection. In this paper, a commercially available Cinchona-alkaloid derivative zwitterionic chiral stationary phase [that is, the CHIRALPAK (R) ZWIX(-)] was successfully used to optimize the enantioresolution of compounds 1-3 under polar-ionic (PI) conditions with a mobile phase consisting of an acetonitrile/methanol 95/5 (v/v) mixture with 80 mM formic acid. With the optimized conditions, enantioseparation and enantioresolution values up to 1.46 and 4.41, respectively, were obtained. In order to assess the applicability of the optimized enantioselective chromatography conditions in real-life scenarios and on MS-based systems, a proof-of-concept application was efficiently carried out by analysing dry urine spot samples spiked with 1 by means of a LC-MS system. The (S)<(R) enantiomer elution order (EEO) was established for compounds 1 and 2 by analysing a pure enantiomeric standard of known configuration. This was not possible for 3 because not commercially available. For this compound, the same EEO was identified applying a procedure based on ab initio time-dependent density-functional theory simulations coupled to electronic circular dichroism analyses. Moreover, a molecular dynamics simulation unveiled the role of the phenolic OH in compound 3 in the retention mechanism. (C) 2021 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Ali, Imran AU - Suhail, Mohd. AU - Asnin, Leonind AU - Aboul-Enein, Hassan Y. TI - Effect of Various Parameters and Mechanism of Reversal Order of Elution in Chiral HPLC JF - CURRENT ANALYTICAL CHEMISTRY J2 - CURR ANAL CHEM VL - 16 PY - 2020 IS - 1 SP - 59 EP - 78 PG - 20 SN - 1573-4110 DO - 10.2174/1573411015666190103145916 UR - https://m2.mtmt.hu/api/publication/31385602 ID - 31385602 N1 - Funding Agency and Grant Number: Department of Science and Technology (DST), New Delhi, IndiaDepartment of Science & Technology (India) [INT/RUS/RFBR/P-238]; Russian Foundation of Basic Research (RFBR), Russia [16-53-45003] Funding text: The authors are thankful to the Department of Science and Technology (DST), New Delhi, India (Project No. INT/RUS/RFBR/P-238) and Russian Foundation of Basic Research (RFBR), Russia (Grant No. 16-53-45003) for funding this work. AB - Background: Chiral separation involves many phenomena in which the elution order of the enantiomers has its unique position. The phenomenon of elution order of the enantiomers has also been used in the determination of optical purity which is favorable to elute the major component after minor enantiomeric impurity but the main problem is that, this phenomenon is rare. Results: This review rumors the reversal order of elution of many chiral molecules in HPLC. Besides, this review pronounces the effects of pH, derivatisation of drugs, the composition of the mobile phase, and temperature on the reversal order of elution of chiral drugs. The efforts are also made to discuss the possible future perspectives of reversal order of elution. Conclusion: Various parameters such as pH, mobile phase composition, temperature, and chemical structure of the analytes play a role in the phenomena of the reversal order of elution of many chiral molecules which are discussed in the article. LA - English DB - MTMT ER - TY - JOUR AU - Bajtai, Attila AU - Ilisz, István AU - Péter, Antal AU - Lindner, Wolfgang TI - Liquid chromatographic resolution of natural and racemic Cinchona alkaloid analogues using strong cation- and zwitterion ion-exchange type stationary phases. Qualitative evaluation of stationary phase characteristics and mobile phase effects on stereoselectivity and retention JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1609 PY - 2020 PG - 13 SN - 0021-9673 DO - 10.1016/j.chroma.2019.460498 UR - https://m2.mtmt.hu/api/publication/31358064 ID - 31358064 LA - English DB - MTMT ER - TY - JOUR AU - Ianni, Federica AU - Cerra, Bruno AU - Shandiz, Shiva Tali AU - Di Michele, Alessandro AU - Saluti, Giorgio AU - Galarini, Roberta AU - Gioiello, Antimo AU - Sardella, Roccaldo AU - Carotti, Andrea TI - Integrating experimental and computational techniques to study chromatographic enantioresolutions of chiral tetrahydroindazole derivatives JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1625 PY - 2020 PG - 10 SN - 0021-9673 DO - 10.1016/j.chroma.2020.461310 UR - https://m2.mtmt.hu/api/publication/31485318 ID - 31485318 AB - With the selection of partially saturated 2H-indazoles as model compounds, we demonstrate the possibility to use Whelk-O1 chiral stationary phases (CSPs) to succeed in efficient small-scale preparative enantioseparations. Runs of three consecutive liquid chromatography injections (about 300 mu g of racemate repeatedly injected in a 100 mu L loop) produced groups of peaks without band contamination (alpha =1.2 and R-s = 2.57). With this procedure approximately 3.0 mg of each enantiomer, with enantiomeric excess >= 97% were obtained. Very profitably, the high volatility of n-hexane used as the sole eluent facilitated the solvent evaporation after the enantiomer recovery. High resolution mass spectrometry analysis confirmed that the chemical identity of the two enantiomers was preserved along the entire process.The ability of Whelk-O1 phases in enantioseparating structurally similar compounds was confirmed with the analysis of other two racemates. Moreover, the relevant chemoselectivity exhibited by the CSP towards the three racemates should allow to simultaneously optimizing the enantioselectivity of different analytes and perform small-scale enantioresolutions of different compounds during the same run. In this study, the integration of experimental off-line electronic circular dichroism analysis with ab initio time-dependent density-functional theory simulations facilitated the assignment of the absolute configuration of the single enantiomers, while a molecular dynamics protocol can be useful to make a priori predictions of the enantioseparation ability of CSP towards selected compounds. (C) 2020 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Bajtai, Attila AU - Szatmári, István AU - Fülöp, Ferenc AU - Lindner, Wolfgang AU - Péter, Antal TI - Enantioseparation of ß-carboline, tetrahydroisoquinoline and benzazepine analogues of pharmaceutical importance: Utilization of chiral stationary phases based on polysaccharides and sulfonic acid modified Cinchonaalkaloids in high-performance liquid and subcritical fluid chromatography JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1615 PY - 2020 PG - 10 SN - 0021-9673 DO - 10.1016/j.chroma.2019.460771 UR - https://m2.mtmt.hu/api/publication/31346573 ID - 31346573 N1 - Funding Agency and Grant Number: Ministry of Human Capacities, Hungarygrant [20391-3/2018/FEKUSTRAT]; [GINOP-2.3.215-2016-00034] Funding text: This work was supported by the project grant GINOP-2.3.215-2016-00034. The Ministry of Human Capacities, Hungarygrant 20391-3/2018/FEKUSTRAT is also acknowledged. The authors highly acknowledge Pilar Franco (Chiral Technologies Europe) for providing the applied columns. We are also thankful to Waters Kft. (Budapest, Hungary) for the loan of the UPC2 system. AB - High-performance liquid chromatographic (HPLC) and subcritical fluid chromatographic (SFC) separations of the enantiomers of structurally diverse, basic beta-carboline, tetrahydroisoquinoline and benzazepine analogues of pharmacological interest were performed applying chiral stationary phases (CSPs) based on (i) neutral polysaccharides- and (ii) zwitterionic sulfonic acid derivatives of Cinchona alkaloids. The aim of this work was to reveal the influence of structural peculiarities on the enantiorecognition on both types of CSP through the investigation of the effects of the composition of the bulk solvent, the structures of the chiral analytes (SAs) and chiral selectors (SOs) on retention and stereoselectivity. As a general tendency, valid for all polysaccharide SOs studied, the increase of the concentration of the apolar component in the mobile phase (n-hexane for LC or liquid CO2 for SFC) was found to significantly increase retention, which in most cases, was accompanied with increased selectivity and resolution. In a way, similar behaviour was registered for the zwitterionic SOs. In polar ionic mode employing eluent systems composed of methanol and acetonitrile with organic acid and base additives, moderate increases in retention factor, selectivity and resolution were observed with increasing acetonitrile content. However, under SFC conditions, an extremely high increase in retention was observed with increased CO2 content, while selectivity and resolution changed only slightly. Thermodynamic parameters derived from temperature dependence studies revealed that separations are controlled by enthalpy. (C) 2020 The Authors. Published by Elsevier B.V. LA - English DB - MTMT ER - TY - BOOK AU - Grushka, Eli AU - Grinberg, Nelu TI - Advances in Chromatography, Volume 50 PB - CRC Press CY - Boca Raton, Florida PY - 2019 SN - 1439858454 UR - https://m2.mtmt.hu/api/publication/32052457 ID - 32052457 LA - English DB - MTMT ER - TY - CHAP AU - Ilisz, István AU - Bajtai, Attila AU - Péter, Antal AU - Lindner, W. ED - Scriba, Gerhard K. E. TI - Cinchona alkaloid-based zwitterionic chiral stationary phases applied for liquid chromatographic enantiomer separations: An overview T2 - Chiral Separations VL - 1985 PB - Springer New York CY - New York, New York SN - 9781493994380 T3 - Methods in Molecular Biology, ISSN 1064-3745 ; 1985. PY - 2019 SP - 251 EP - 277 PG - 27 DO - 10.1007/978-1-4939-9438-0_14 UR - https://m2.mtmt.hu/api/publication/30789549 ID - 30789549 N1 - Institute of Pharmaceutical Analysis, University of Szeged, Szeged, Hungary Department of Analytical Chemistry, University of Vienna, Vienna, Austria Export Date: 5 September 2019 Correspondence Address: Ilisz, I.; Institute of Pharmaceutical Analysis, University of SzegedHungary; email: ilisz@chem.u-szeged.hu AB - For the early 2000s, chromatographic methods applying chiral stationary phases (CSPs) became the most effective techniques for the resolution of chiral compounds on both analytical and preparative scales. High-performance liquid chromatography (HPLC) employing various types of chiral selectors covalently bonded to silica-based supports offers a state-of-the-art methodology for "chiral analysis." Although a large number of CSPs are available nowadays, the design and development of new "chiral columns" are still needed since it is obvious that in practice one needs a good portfolio of different columns to face the challenging task of enantiomeric resolutions. The development of the unique chiral anion, cation, and zwitterion exchangers achieved by Lindner and his partners serves as an expansion of the range of the efficiently applicable CSPs. In this context this overview chapter discusses and summarizes direct enantiomer separations of chiral acids and ampholytes applying zwitterionic ion exchangers derived from Cinchona alkaloids. Our aim is to provide comprehensive information on practical solutions with focus on the molecular recognition and methodological variables. © Springer Science+Business Media, LLC, part of Springer Nature 2019. LA - English DB - MTMT ER - TY - JOUR AU - Fernandes, Carla AU - Phyo, Ye' Zaw AU - Silva, Ana Sofia AU - Tiritan, Maria Elizabeth AU - Kijjoa, Anake AU - Pinto, Madalena M M TI - Chiral Stationary Phases Based on Small Molecules: An Update of the Last 17 Years JF - SEPARATION AND PURIFICATION REVIEWS J2 - SEP PURIF REV VL - 47 PY - 2018 IS - 2 SP - 89 EP - 123 PG - 35 SN - 1542-2119 DO - 10.1080/15422119.2017.1326939 UR - https://m2.mtmt.hu/api/publication/27349036 ID - 27349036 N1 - Funding Agency and Grant Number: FCT/MCTES-Foundation for Science and Technology from the Minister of Science, Technology and Higher Education (PIDDAC); European Regional Development Fund (ERDF) through the COMPETE-Programa Operacional Factores de Competitividade (POFC) programmeEuropean Union (EU) [UID/Multi/04423/2013, PTDC/MAR-BIO/4694/2014, POCI-01-0145-FEDER-016790]; project INNOVMAR-Innovation and Sustainability in the Management and Exploitation of Marine Resources (within Research Line NOVELMAR) [NORTE-01-0145-FEDER-000035]; North Portugal Regional Operational Programme (NORTE) under the PORTUGAL Partnership Agreement, through the European Regional Development Fund (ERDF); COXANT-CESPU; Erasmus Mundus Action 2 (Lotus Plus project) Funding text: This work was partially supported through national funds provided by FCT/MCTES-Foundation for Science and Technology from the Minister of Science, Technology and Higher Education (PIDDAC) and European Regional Development Fund (ERDF) through the COMPETE-Programa Operacional Factores de Competitividade (POFC) programme, under the Strategic Funding UID/Multi/04423/2013, the project PTDC/MAR-BIO/4694/2014 (reference POCI-01-0145-FEDER-016790; Project 3599-Promover a Producao Cientifica e Desenvolvimento Tecnologico e a Constituicao de Redes Tematicas (3599-PPCDT)) in the framework of the programme PT2020 as well as by the project INNOVMAR-Innovation and Sustainability in the Management and Exploitation of Marine Resources (reference NORTE-01-0145-FEDER-000035, within Research Line NOVELMAR), supported by North Portugal Regional Operational Programme (NORTE 2020), under the PORTUGAL 2020 Partnership Agreement, through the European Regional Development Fund (ERDF) and COXANT-CESPU-2016. Y.Z. Phyo thanks the Erasmus Mundus Action 2 (Lotus Plus project) for a PhD scholarship. LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Bajtai, Attila AU - Lindner, W AU - Péter, Antal TI - Liquid chromatographic enantiomer separations applying chiral ion-exchangers based on Cinchona alkaloids JF - JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS J2 - J PHARMACEUT BIOMED ANAL VL - 159 PY - 2018 SP - 127 EP - 152 PG - 26 SN - 0731-7085 DO - 10.1016/j.jpba.2018.06.045 UR - https://m2.mtmt.hu/api/publication/3407106 ID - 3407106 AB - As the understanding of the various biological actions of compounds with different stereochemistry has grown, the necessity to develop methods for the analytical qualification and quantification of chiral products has become particularly important. The last quarter of the century has seen a vast growth of diverse chiral technologies, including stereocontrolled synthesis and enantioselective separation and analysis concepts. By the introduction of covalently bonded silica-based chiral stationary phases (CSPs), the so-called direct liquid chromatographic (LC) methods of enantiomer separation became the state-of-the-art methodology. Although a large number of CSPs is available nowadays, the design and development of new chiral selectors and CSPs are still needed since it is obvious that in practice one needs a good portfolio of different CSPs and focused “chiral columns” to tackle the challenging tasks. This review discusses and summarizes direct enantiomer separations of chiral acids and ampholytes applying anionic and zwitterionic ion-exchangers derived from Cinchona alkaloids with emphasis on literature data published in the last 10 years. Our aim is to provide an overview of practical solutions, while focusing on the integration of molecular recognition and methodological variables. © 2018 Elsevier B.V. LA - English DB - MTMT ER - TY - JOUR AU - Vargas-Caporali, Jorge AU - Juaristi, Eusebio TI - Determination of Enantioselectivities by Means of Chiral Stationary Phase HPLC in Order to Identify Effective Proline-Derived Organocatalysts JF - JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY J2 - J BRAZIL CHEM SOC VL - 29 PY - 2018 IS - 5 SP - 896 EP - 915 PG - 20 SN - 0103-5053 DO - 10.21577/0103-5053.20170211 UR - https://m2.mtmt.hu/api/publication/27604034 ID - 27604034 N1 - Funding Agency and Grant Number: National Council of Science and Technology (CONACYT, Mexico)Consejo Nacional de Ciencia y Tecnologia (CONACyT) [CB-2013/220945] Funding text: The authors acknowledge financial support via grant CB-2013/220945 from the National Council of Science and Technology (CONACYT, Mexico). The authors also thank Dr Carmen Giovana Granados Ramirez for helpful technical assistance about HPLC. LA - English DB - MTMT ER - TY - CHAP AU - Asnin, L.D. AU - Cavazzini, A. AU - Marchetti, N. ED - Eli, Grushka ED - Nelu, Grinberg TI - Solute-stationary phase interaction in chiral chromatography T2 - Advances in Chromatography, Volume 53 VL - 53 PB - CRC Press - Taylor and Francis Group CY - Boca Raton, Florida SN - 9781498726801 T3 - Advances in Chromatography, ISSN 0065-2415 ; 53. PY - 2017 SP - 1 EP - 73 PG - 73 UR - https://m2.mtmt.hu/api/publication/32002570 ID - 32002570 N1 - Export Date: 7 May 2021 CODEN: ADCYA Export Date: 10 May 2021 CODEN: ADCYA LA - English DB - MTMT ER - TY - JOUR AU - Orosz, Tímea AU - Grecsó, Nóra AU - Lajkó, Gyula AU - Szakonyi, Zsolt AU - Fülöp, Ferenc AU - Armstrong, DW AU - Ilisz, István AU - Péter, Antal TI - Liquid chromatographic enantioseparation of carbocyclic β-amino acids possessing limonene skeleton on macrocyclic glycopeptide-based chiral stationary phases JF - JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS J2 - J PHARMACEUT BIOMED ANAL VL - 145 PY - 2017 SP - 119 EP - 126 PG - 8 SN - 0731-7085 DO - 10.1016/j.jpba.2017.06.010 UR - https://m2.mtmt.hu/api/publication/3256483 ID - 3256483 N1 - ISSN:0731-7085 AB - Polar-ionic and reversed-phase high-performance liquid chromatographic separations of limonene-based cyclic β-amino acid enantiomers were carried out by using macrocyclic glycopeptide-based chiral selectors applying Chirobiotic T, TAG and R columns. The effects of additives, concentration of the co- and counter-ions and the temperature in polar-ionic mobile phase systems were studied. The influence of pH, MeOH content and alcohol additives were investigated in the reversed-phase mode. The difference in the change in standard enthalpy Δ(ΔH°), entropy Δ(ΔS°), and free energy Δ(ΔG°) was calculated from the linear van't Hoff plots derived from the ln α vs 1/T curves in the temperature range 5–40 °C. Unusual temperature behavior was observed on Chirobiotic TAG for most of the analytes: decreased retention times were accompanied with increased separation factors with increasing temperature, and separation was entropically-driven. For two of the studied analytes enthalpically-driven enantioseparations were observed. The elution sequence was determined in all cases, but no general rule could be established. © 2017 Elsevier B.V. LA - English DB - MTMT ER - TY - JOUR AU - Gerhardt, Heike AU - Sievers-Engler, Adrian AU - Jahanshah, Ghazaleh AU - Pataj, Zoltan AU - Ianni, Federica AU - Gross, Harald AU - Lindner, Wolfgang AU - Laemmerhofer, Michael TI - Methods for the comprehensive structural elucidation of constitution and stereochemistry of lipopeptides JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1428 PY - 2016 SP - 280 EP - 291 PG - 12 SN - 0021-9673 DO - 10.1016/j.chroma.2015.05.065 UR - https://m2.mtmt.hu/api/publication/25633787 ID - 25633787 LA - English DB - MTMT ER - TY - JOUR AU - Grecsó, Nóra AU - Forro, E AU - Fulop, F AU - Péter, Antal AU - Ilisz, István AU - Lindner, W TI - Combinatorial effects of the configuration of the cationic and the anionic chiral subunits of four zwitterionic chiral stationary phases leading to reversal of elution order of cyclic beta(3)-amino acid enantiomers as ampholytic model compounds JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1467 PY - 2016 SP - 178 EP - 187 PG - 10 SN - 0021-9673 DO - 10.1016/j.chroma.2016.05.041 UR - https://m2.mtmt.hu/api/publication/3150585 ID - 3150585 N1 - Funding Agency and Grant Number: Hungarian National Science Foundation [OTKA K 108847] Funding text: This work was supported by Hungarian National Science Foundation grant OTKA K 108847. We gratefully thank Pilar Franco (Chiral Technologies Europe, Illkirch, France) for the provision of the Cinchona alkaloid-based columns of the CSP-1 and CSP-2 type. CSP-4 was provided by Dr. Michal Kohout (Department of Organic Chemistry, Institute of Chemical Technology, Prague, Czech Republic). We also thank Dr. Kevin Schug (University of Arlington, Texas, USA) for proofreading the article. ISSN:0021-9673 AB - In a systematic way enantioseparations of non-methylated and the corresponding N-monomethylated ampholytic cyclic beta(3)-aminoacids were carried out on four zwitterionic chiral stationary phases (CSPs; ZWIX(+)(TM), ZWIX(-)(TM), ZWIX(+A), ZWIX(-A)). CSPs were based on the combinations of quinine and quinidine as the cationic and of (R,R)- and (S,S)-aminocyclohexane sulfonic acid as the anionic sites. In polar-ionic mobile phase systems, the effects of the composition of the bulk solvents, the additives, the concentration of the co- and counter-ions, the temperature, and the structures of the ampholytic analytes were investigated. The changes in standard enthalpy, Delta(Delta H degrees), entropy, Delta(Delta S degrees), and free energy, Delta(Delta G degrees), were calculated from the linear van't Hoff plots derived from the In alpha vs 1/T curves in the studied temperature range (5-40 degrees C). Unusual temperature behavior was observed on the ZWIX(-)(TM) column: decreased retention times were accompanied by increased separation factors with increasing temperature, and separation was entropically-driven. For the other three CSPs, enthalpically-driven enantioseparations were observed. Via the consequent determination of the elution order of the resolved enantiomers, the effects of the absolute configuration of the chiral anionic and cationic subunits of the zwitterionic CSPs could be elucidated. N-methylation of the amino acids led unexpectedly to a reversal of the elution sequence, which can be interpreted by a subtle shift of the hierarchical order of the sterically most important driving interaction sites from the cationic to the anionic units, and vice versa. (C) 2016 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Grecsó, Nóra AU - Kohout, M AU - Carotti, A AU - Sardella, R AU - Natalini, B AU - Fülöp, Ferenc AU - Lindner, W AU - Péter, Antal AU - Ilisz, István TI - Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds JF - JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS J2 - J PHARMACEUT BIOMED ANAL VL - 124 PY - 2016 SP - 164 EP - 173 PG - 10 SN - 0731-7085 DO - 10.1016/j.jpba.2016.02.043 UR - https://m2.mtmt.hu/api/publication/3040887 ID - 3040887 AB - The enantiomers of trans-paroxetine were separated on four chiral stationary phases (CSPs) based on chiral zwitterionic Cinchona alkaloids fused with (R,R)- or (S,S)-trans-2-aminocyclohexanesulfonic acid. The enantioseparations were carried out in polar-ionic or in hydro-organic mobile phases with MeOH/THF, MeCN/THF, MeCN/THF/H2O and MeOH/MeCN/THF containing organic acid and base additives, in the temperature range 0-50 °C. The effects of the mobile phase composition, the natures and concentrations of the additives and temperature on the separations were investigated. Thermodynamic parameters were calculated from plots of ln α vs 1/T. δ(δH°) ranged between -3.0 and +1.5 kJ mol-1, and δ(δS°) between -8.8 and +5.9 J mol-1 K-1. The enantioseparation was generally enthalpically controlled, the retention factor and separation factor decreasing with increasing temperature, but entropically controlled separation was also observed. The elution sequences of the paroxetine enantiomers on the two pairs of pseudo-enantiomeric CSPs were investigated, and an attempt was made to explain the observed anomalies in silico in order to gain an insight into the underlying molecular recognition events between the four chiral selectors and the analyte enantiomers. © 2016 Elsevier B.V. LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Péter, Antal AU - Lindner, W TI - State-of-the-art enantioseparations of natural and unnatural amino acids by high-performance liquid chromatography JF - TRAC-TRENDS IN ANALYTICAL CHEMISTRY J2 - TRAC-TREND ANAL CHEM VL - 81 PY - 2016 SP - 11 EP - 22 PG - 12 SN - 0165-9936 DO - 10.1016/j.trac.2016.01.016 UR - https://m2.mtmt.hu/api/publication/3103586 ID - 3103586 N1 - Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, Szeged, H-6720, Hungary Department of Analytical Chemistry, University of Vienna, Währinger Strasse 38, Vienna, 1090, Austria Cited By :37 Export Date: 24 September 2019 CODEN: TTAED Correspondence Address: Lindner, W.; Department of Analytical Chemistry, University of Vienna, Währinger Strasse 38, Austria; email: wolfgang.lindner@univie.ac.at Chemicals/CAS: 1,3 dinitrobenzene, 99-65-0; 2,4 dinitrophenol, 25550-58-7, 51-28-5 Funding details: Hungarian Science Foundation Funding details: Hungarian Scientific Research Fund, K 108847 Funding text 1: This work was supported by Hungarian National Science Foundation grant OTKA K 108847 . AB - This review discusses recent publications on the separation and analysis of natural and unnatural amino acid enantiomers by liquid chromatography. Focus is placed on methodological aspects relating chiral stationary phases and chiral columns which can cope with the challenge. Conceptually, amino acids can be enantioseparated in free form, which refers to the resolution of polar ampholytes, or as N-protected amino acids, which can be regarded as acidic commodities. Such synthons are used, for instance, in peptide synthesis protocols. Amino groups are frequently tagged with highly fluorescent or MS/MS active labels in order to generate sensitive and simultaneously stereoselective assays of diverse amino acids in complex matrices. It is our intention to present the state of the art of enantioselective amino acid analysis by HPLC concepts and to pinpoint practical aspects. (C) 2016 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Scriba, Gerhard K E TI - Chiral recognition in separation science - an update JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1467 PY - 2016 SP - 56 EP - 78 PG - 23 SN - 0021-9673 DO - 10.1016/j.chroma.2016.05.061 UR - https://m2.mtmt.hu/api/publication/26878126 ID - 26878126 LA - English DB - MTMT ER - TY - JOUR AU - Zhang, Tong AU - Holder, Emilie AU - Franco, Pilar AU - Laemmerhofer, Michael AU - Sievers-Engler, Adrian AU - Gerhardt, Heike AU - Gross, Harald AU - Lindner, Wolfgang TI - Peptide Analysis: Zwitterionic Chiral Ion-Exchangers as Complementary Option to HILIC and to Reversed-Phase Chromatography JF - LC GC EUROPE J2 - LC GC EUR VL - 29 PY - 2016 IS - 3 SP - 112 EP - + PG - 10 SN - 1471-6577 UR - https://m2.mtmt.hu/api/publication/26878136 ID - 26878136 N1 - Funding Agency and Grant Number: Struktur- and Innovationsfonds Baden-Wurttemberg (SI-BW); German Research Foundation DFGGerman Research Foundation (DFG) [INST 37/821-1 FUGG] Funding text: M.L. acknowledges the support by the "Struktur- and Innovationsfonds Baden-Wurttemberg (SI-BW)" and by the German Research Foundation DFG for funding scientific equipment as part of the DFG's Major Research Instrumentation Programme as per Art.91b GG (INST 37/821-1 FUGG). LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Grecsó, Nóra AU - Misicka, A AU - Tymecka, D AU - Lázár, László AU - Lindner, W AU - Péter, Antal TI - Comparison of the separation performances of cinchona alkaloid-based zwitterionic stationary phases in the enantioseparation of β2- And β3-amino acids JF - MOLECULES J2 - MOLECULES VL - 20 PY - 2015 IS - 1 SP - 70 EP - 87 PG - 18 SN - 1420-3049 DO - 10.3390/molecules20010070 UR - https://m2.mtmt.hu/api/publication/2833796 ID - 2833796 N1 - Funding Agency and Grant Number: Hungarian National Science Foundation [OTKA K 108847] Funding text: This work was supported by Hungarian National Science Foundation grant OTKA K 108847. The support of Pilar Franco (Chiral Technologies Europe) in providing the Chiralpak columns is gratefully acknowledged. AB - The enantiomers of twelve unusual β2- and β3-homoamino acids containing the same side-chains were separated on chiral stationary phases containing a quinine- or quinidine-based zwitterionic ion-exchanger as chiral selector. The effects of the mobile phase composition, the nature and concentration of the acid and base additives and temperature on the separations were investigated. The changes in standard enthalpy, Δ(ΔH° ), entropy, Δ(ΔS° ), and free energy, Δ(ΔG° ), were calculated from the linear van't Hoff plots derived from the ln α vs. 1/T curves in the studied temperature range (10-50 °C). The values of the thermodynamic parameters depended on the nature of the selectors, the structures of the analytes, and the positions of the substituents on the analytes. A comparison of the zwitterionic stationary phases revealed that the quinidine-based ZWIX(-)™ column exhibited much better selectivity for both β2- and β 3-amino acids than the quinine-based ZWIX(+)™ column, and the separation performances of both the ZWIX(+)™ and ZWIX(-)™ columns were better for β2-amino acids. The elution sequence was determined in some cases and was observed to be R < S and S < R on the ZWIX(+)™ and ZWIX(-)™ columns, respectively. LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Grecsó, Nóra AU - Fülöp, Ferenc AU - Lindner, Wolfgang AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of cationic 1,2,3,4-tetrahydroisoquinoline analogs on Cinchona alkaloid-based zwitterionic chiral stationary phases JF - ANALYTICAL AND BIOANALYTICAL CHEMISTRY J2 - ANAL BIOANAL CHEM VL - 407 PY - 2015 IS - 3 SP - 961 EP - 972 PG - 12 SN - 1618-2642 DO - 10.1007/s00216-014-8247-0 UR - https://m2.mtmt.hu/api/publication/2852283 ID - 2852283 N1 - Funding Agency and Grant Number: OTKAOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [T 108847] Funding text: This work was supported by OTKA grant T 108847. A.P. is grateful to Pilar Franco for the ZWIX(+)(TM) and ZWIX(-)(TM) columns. AB - The stereoisomers of 1,2,3,4-tetrahydroisoquinoline analogs were resolved for the first time by applying a polar ionic mobile phase on a quinine or a quinidine moiety fused with a chiral sulfonic acid-type chiral selector immobilized on silica [Chiralpak ZWIX(+)(TM) and Chiralpak ZWIX(-)(TM)]. The effects of the nature and concentrations of the mobile phase components and additives and temperature on the retention and enantioseparation on the investigated chiral columns were studied. Experiments were performed in the temperature range 10-50 A degrees C. Thermodynamic parameters were calculated from plots of ln alpha versus 1/T. The separations were generally enthalpy-controlled, but entropy-controlled separation was also observed below 30 A degrees C. The enantiomer elution order was determined in some cases and was observed to be opposite on the ZWIX(+)(TM) and ZWIX(-)(TM) columns. Our results contribute to a better understanding of the enantiorecognition mechanism of chiral bases with chiral zwitterionic selectors. LA - English DB - MTMT ER - TY - JOUR AU - Remelli, Maurizio AU - Pozzati, Giovanni AU - Conato, Chiara TI - Direct chiral resolution of underivatized amino acids on a stationary phase dynamically modified with the ion-exchanger N '-decyl-L-spinacine JF - JOURNAL OF SEPARATION SCIENCE J2 - J SEP SCI VL - 38 PY - 2015 IS - 6 SP - 894 EP - 900 PG - 7 SN - 1615-9306 DO - 10.1002/jssc.201401381 UR - https://m2.mtmt.hu/api/publication/24876313 ID - 24876313 N1 - Cited By :5 Export Date: 29 June 2023 CODEN: JSSCC Correspondence Address: Remelli, M.; Dipartimento di Scienze Chimiche e Farmaceutiche, via Fossato di Mortara 17, Italy; email: rmm@unife.it Chemicals/CAS: amino acid, 65072-01-7; Amino Acids; Imidazoles; Pyridines; spinacine LA - English DB - MTMT ER - TY - JOUR AU - Tanwar, S AU - Bhushan, R TI - Enantioresolution of Amino Acids: A Decade's Perspective, Prospects and Challenges JF - CHROMATOGRAPHIA J2 - CHROMATOGRAPHIA VL - 78 PY - 2015 IS - 17-18 SP - 1113 EP - 1134 PG - 22 SN - 0009-5893 DO - 10.1007/s10337-015-2933-8 UR - https://m2.mtmt.hu/api/publication/25040020 ID - 25040020 N1 - Cited By :31 Export Date: 29 June 2023 CODEN: CHRGB Correspondence Address: Tanwar, S.; Department of Chemistry and Industrial Chemistry, University of Genoa, Via Dodecaneso 31, Italy Chemicals/CAS: alpha cyclodextrin, 10016-20-3; amino acid, 65072-01-7; beta cyclodextrin, 7585-39-9; chloride, 16887-00-6; gamma cyclodextrin, 17465-86-0; isothiocyanic acid, 3129-90-6, 71048-69-6; thiol derivative, 13940-21-1 LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Grecsó, Nóra AU - Palkó, Márta AU - Fülöp, Ferenc AU - Lindner, W AU - Péter, Antal TI - Structural and temperature effects on enantiomer separations of bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids on cinchona alkaloid-based zwitterionic chiral stationary phases JF - JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS J2 - J PHARMACEUT BIOMED ANAL VL - 98 PY - 2014 SP - 130 EP - 139 PG - 10 SN - 0731-7085 DO - 10.1016/j.jpba.2014.05.012 UR - https://m2.mtmt.hu/api/publication/2702824 ID - 2702824 N1 - Funding Agency and Grant Number: Hungarian National Science Foundation [OTKA K 108847] Funding text: This work was supported by Hungarian National Science Foundation grant OTKA K 108847. A.P gratefully thanks to Pilar Franco (Chiral Technologies Europe) for providing the Chiralpak columns. ISSN:0731-7085 AB - Procedures for the direct high-performance liquid chromatographic enantiomer separation of four bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids were developed in polar-ionic mode on zwitterionic chiral stationary phases (CSPs) based on cinchonane alkaloide quinine, quinidine and chiral sulfonic acid motifs. The effects of the mobile phase composition including the type of acid and base additives, the structures of the analytes and temperature were investigated. Experiments were performed at constant mobile phase compositions in the temperature range 10-50. °C in order to study the effects of temperature, and thermodynamic parameters were calculated from plots of ln k or ln α vs. 1/. T. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes. It was found that the enantiomeric separations were in most cases enthalpically driven, but entropically driven separation was also observed. The sequence of elution of the enantiomers on the pseudo-enantiomerically behaving CSPs was determined in all cases. © 2014 Elsevier B.V. LA - English DB - MTMT ER - TY - JOUR AU - Laemmerhofer, Michael TI - Liquid chromatographic enantiomer separation with special focus on zwitterionic chiral ion-exchangers JF - ANALYTICAL AND BIOANALYTICAL CHEMISTRY J2 - ANAL BIOANAL CHEM VL - 406 PY - 2014 IS - 25 SP - 6095 EP - 6103 PG - 9 SN - 1618-2642 DO - 10.1007/s00216-014-7930-5 UR - https://m2.mtmt.hu/api/publication/25611151 ID - 25611151 LA - English DB - MTMT ER - TY - JOUR AU - Zhang, Tong AU - Holder, Emilie AU - Franco, Pilar AU - Lindner, Wolfgang TI - Method development and optimization on cinchona and chiral sulfonic acid-based zwitterionic stationary phases for enantiomer separations of free amino acids by high-performance liquid chromatography JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1363 PY - 2014 SP - 191 EP - 199 PG - 9 SN - 0021-9673 DO - 10.1016/j.chroma.2014.06.012 UR - https://m2.mtmt.hu/api/publication/24876541 ID - 24876541 LA - English DB - MTMT ER - TY - JOUR AU - Zhang, Tong AU - Holder, Emilie AU - Franco, Pilar AU - Lindner, Wolfgang TI - Zwitterionic chiral stationary phases based on cinchona and chiral sulfonic acids for the direct stereoselective separation of amino acids and other amphoteric compounds JF - JOURNAL OF SEPARATION SCIENCE J2 - J SEP SCI VL - 37 PY - 2014 IS - 11 SP - 1237 EP - 1247 PG - 11 SN - 1615-9306 DO - 10.1002/jssc.201400149 UR - https://m2.mtmt.hu/api/publication/26878137 ID - 26878137 LA - English DB - MTMT ER -