TY - JOUR AU - Pálinkás, Noémi AU - Mikle, Gábor AU - Aranyi, Anita AU - Péter, Antal AU - Kollár, László TI - Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2'-Diamino-1,1'-binaphthalene in the Presence of Palladium Catalysts JF - CHEMISTRYSELECT J2 - CHEMISTRYSELECT VL - 5 PY - 2020 IS - 35 SP - 11048 EP - 11051 PG - 4 SN - 2365-6549 DO - 10.1002/slct.202002093 UR - https://m2.mtmt.hu/api/publication/31625419 ID - 31625419 N1 - Funding Agency and Grant Number: Hungarian Scientific Research Fund [OTKA K113177, GINOP-2.3.2-15-2016-00049] Funding text: The authors thank the Hungarian Scientific Research Fund (OTKA K113177) for the financial support. This work was also supported by the GINOP-2.3.2-15-2016-00049 grant. AB - Palladium-catalysed aminocarbonylation of iodobenzene and 1-iodocyclohexene with both enantiomerically pure and racemic 2,2'-diamino-1,1'-binaphthalene (BINAM) asN-nucleophile was carried out. The mono- and dicarboxamide enantiomers possessing axial chirality were synthesised using (S-ax)-BINAM. In the possession of these reference compounds the partial chiral kinetic resolution of racemic BINAM was carried out using various optically active bidentate ligands such as (2S,4S)-BDPP, (2S,3S)-CHIRAPHOS and (R)-BINAP. It was revealed by chiral HPLC measurements that up to 10 % enantiomeric excess of carboxamides can be achieved in this way. Although with low enantioselection, enantioselectve aminocarbonylation was carried out for the first time. LA - English DB - MTMT ER - TY - JOUR AU - Aranyi, Anita AU - Ilisz, István AU - Péter, Antal AU - Fülöp, Ferenc AU - West, C TI - Exploring the enantioseparation of amino-naphthol analogues by supercritical fluid chromatography JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1387 PY - 2015 SP - 123 EP - 133 PG - 11 SN - 0021-9673 DO - 10.1016/j.chroma.2015.01.084 UR - https://m2.mtmt.hu/api/publication/2869802 ID - 2869802 N1 - Funding Agency and Grant Number: Campus France Funding text: Yingru Zhang (Bristol-Myers Squibb) and Pilar Franco (Chiral Technologies) are acknowledged for the kind gift of columns. We are grateful to Waters for the Acquity UPC2 system let at our disposal. Campus France is acknowledged for the grant allowed to Miss Aranyi. AB - The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1-naphthol analogues and 2-(1-amino-2-methylpropyl)-1-naphthol) was investigated in supercritical fluid chromatography. Five commercially available chiral stationary phases based on immobilized polysaccharide chiral selectors (Chiralpak IA, IB, IC, ID and IE) were evaluated. Chiralpak IB was by far the most efficient to achieve the separation of these racemates and was further selected for optimization of elution conditions. The effects of column temperature (varying between 5 and 45. °C) and co-solvent added to carbon dioxide (methanol, ethanol, isopropanol and dichloromethane) were investigated. A particular attention was paid to mobile-phase additives. Several of them, acids, bases or salts (namely water, formic acid, acetic acid, trifluoroacetic acid, diethylamine, diethanolamine, triethylamine, triethanolamine, dimethylethanolamine, ammonia and ammonium acetate), were tested in order to improve peak shapes while maintaining selectivity. With the help of other achiral naphthol derivatives, the additive effects were examined. LA - English DB - MTMT ER - TY - THES AU - Aranyi, Anita TI - Poliszacharid és ciklofruktán típusú királis állófázisok alkalmazása enantiomerek elválasztására PB - Szegedi Tudományegyetem (SZTE) PY - 2014 SP - 92 DO - 10.14232/phd.2356 UR - https://m2.mtmt.hu/api/publication/2818947 ID - 2818947 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Aranyi, Anita AU - Pataj, Zoltán AU - Ilisz, István AU - Péter, Antal TI - Aminonaftol enantiomerek nagyhatékonyságú folyadékkromatográfiás vizsgálata: A hőmérséklet hatása a királis elválasztásra JF - MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-) J2 - MAGY KÉM FOLY KÉM KÖZL VL - 120 PY - 2014 IS - 2-3 SP - 60 EP - 66 PG - 7 SN - 1418-9933 UR - https://m2.mtmt.hu/api/publication/2790838 ID - 2790838 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Pataj, Zoltán AU - Aranyi, Anita AU - Ilisz, István AU - Péter, Antal TI - Nagyhatékonyságú folyadékkromatográfiás enantiomerelválasztás: ß-aminosavak viselkedése antibiotikum szelektorokon JF - MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-) J2 - MAGY KÉM FOLY KÉM KÖZL VL - 120 PY - 2014 IS - 2-3 SP - 45 EP - 49 PG - 5 SN - 1418-9933 UR - https://m2.mtmt.hu/api/publication/2790835 ID - 2790835 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Aranyi, Anita AU - Péter, Antal AU - Ilisz, István AU - Fülöp, Ferenc AU - Scriba, GKE TI - Cyclodextrin-mediated enantioseparation of phenylalanine amide derivatives and amino alcohols by capillary electrophoresis-Role of complexation constants and complex mobilities JF - ELECTROPHORESIS J2 - ELECTROPHORESIS VL - 35 PY - 2014 IS - 19 SP - 2848 EP - 2854 PG - 7 SN - 0173-0835 DO - 10.1002/elps.201400142 UR - https://m2.mtmt.hu/api/publication/2770770 ID - 2770770 AB - The separation of the enantiomers of phenylalanine amide and N-methyl derivatives as well as some amino alcohols was studied by CE in acidic BGEs using CDs as chiral selectors. The native CDs displayed only low chiral recognition ability at a concentration of 15 mg/mL in 20 mM sodium phosphate buffer, pH 2.5. In contrast, the analyte enantiomers were separated in the presence of randomly sulfated CDs under reversed polarity of the applied voltage. Sulfated β-CD proved to be the most universal selector resulting in the enantioseparation of all analytes. Opposite enantiomer migration order depending on the size of the CD cavity was observed for phenylalanine amide and 2-amino-2-phenylethanol. The R-enantiomers migrated first in the presence of sulfated α-CD and γ-CD while the S-enantiomers were detected first in the presence of sulfated β-CD. The enantioseparations could be rationalized based on analyte complexation by the respective CDs except for 2-amino-2-phenylethanol and sulfated β-CD where essentially equal complexation constants were derived for the enantiomers. In this case, the migration behavior could be attributed to the mobilities of the enantiomer-CD complexes adding another example to the CE-specific phenomenon of enantioseparations based primarily on complexmobilities. LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Grecsó, Nóra AU - Aranyi, Anita AU - Suchotin, P AU - Tymecka, D AU - Wilenska, B AU - Misicka, A AU - Fülöp, Ferenc AU - Lindner, W AU - Péter, Antal TI - Enantioseparation of β2-amino acids on cinchona alkaloid-based zwitterionic chiral stationary phases. Structural and temperature effects JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1334 PY - 2014 SP - 44 EP - 54 PG - 11 SN - 0021-9673 DO - 10.1016/j.chroma.2014.01.075 UR - https://m2.mtmt.hu/api/publication/2547618 ID - 2547618 N1 - Funding Agency and Grant Number: Hungarian National Science Foundation [OM K 108847, TeT-10-1-2011-0055]; Pilar Franco (Chiral Technologies Europe); TAMOP [4.2.4. A/2-11-1-2012-0001]; European Union; European Social Fund; European Regional Development Fund under the Operational Program Innovative Economy Funding text: This work was supported by Hungarian National Science Foundation grant OM K 108847 and TeT-10-1-2011-0055. The support of Pilar Franco (Chiral Technologies Europe) in providing of Chiralpak columns is gratefully acknowledged. The research of N.G. was realized in the frames of TAMOP 4.2.4. A/2-11-1-2012-0001 "National Excellence Program - Elaborating and operating an inland student and researcher personal support system convergence program. The project was subsidized by the European Union and co-financed by the European Social Fund". "The study was carried out at the Biological and Chemical Research Center, University of Warsaw, established within the project co-financed by EU from the European Regional Development Fund under the Operational Program Innovative Economy, 2007-2013, and with the use of CeePT infrastructure financed by the same EU programme". AB - The enantiomers of sixteen unusual β2-amino acids were directly separated on chiral stationary phases containing quinine- or quinidine-based zwitterionic selectors. The effects of the mobile phase composition, the structure of the analyte and temperature on the separations were investigated. Experiments were performed at constant mobile phase compositions in the temperature range -5 to 55°C in order to study the effects of temperature, and thermodynamic parameters were estimated from plots of lnk or lnα 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 was determined in some cases. © 2014 Elsevier B.V. LA - English DB - MTMT ER - TY - JOUR AU - Aranyi, Anita AU - Ilisz, István AU - Grecsó, Nóra AU - Csütörtöki, Renáta AU - Szatmári, István AU - Fülöp, Ferenc AU - Péter, Antal TI - Development of the high-performance liquid chromatographic method for the enantioseparation of unusual glycine ester analogs on polysaccharide-based chiral stationary phases JF - JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS J2 - J PHARMACEUT BIOMED ANAL VL - 76 PY - 2013 SP - 183 EP - 191 PG - 9 SN - 0731-7085 DO - 10.1016/j.jpba.2012.12.030 UR - https://m2.mtmt.hu/api/publication/2238778 ID - 2238778 N1 - Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary Cited By :4 Export Date: 3 April 2023 CODEN: JPBAD Correspondence Address: Péter, A.; Department of Inorganic and Analytical Chemistry, Dóm tér 7, H-6720 Szeged, Hungary; email: apeter@chem.u-szeged.hu Chemicals/CAS: alcohol, 64-17-5; diethylamine, 109-89-7, 660-68-4; heptane, 142-82-5, 3356-67-0; Esters; Glycine, 56-40-6; Polysaccharides AB - The stereoisomers of ten unusual amino acid analogs, 1- and 2-naphthol-substituted glycine and its ester derivatives, were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenylcarbamate) (Cellulose-1), cellulose tris-(3-chloro-4-methylphenylcarbamate) (Cellulose-2), cellulose tris-(4-methylbenzoate) (Cellulose-3), cellulose tris-(4-chloro-3-methylphenylcarbamate) (Cellulose-4) and amylose tris-(5-chloro-2-methylphenylcarbamate) (Amylose-2). Experiments were performed in normal-phase mode with n-heptane/alcohol/diethylamine mobile phases in a wide temperature range: 5-50 degrees C. Thermodynamic parameters were calculated from plots of In k or In alpha vs. 1/T. Delta(Delta H degrees) ranged from -10.1 to 6.2 kJ mol(-1), Delta(Delta S degrees) from -31.5 to 22.5 J mol(-1) K-1 and -Delta(Delta G degrees) from 0.4 to 1.4 kJ mol(-1), and both enthalpy and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature. The sequence of elution of the stereoisomers was determined in some cases. (C) 2013 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Aranyi, Anita AU - Bagi, Ágnes AU - Ilisz, István AU - Pataj, Zoltán AU - Fülöp, Ferenc AU - Armstrong, DW AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of amino compounds on newly developed cyclofructan-based chiral stationary phases JF - JOURNAL OF SEPARATION SCIENCE J2 - J SEP SCI VL - 35 PY - 2012 IS - 5-6 SP - 617 EP - 624 PG - 8 SN - 1615-9306 DO - 10.1002/jssc.201100921 UR - https://m2.mtmt.hu/api/publication/2046793 ID - 2046793 AB - Direct separation of the enantiomers of amino acid amines, amino alcohols, and diamines was performed on recently developed chiral stationary phases containing isopropyl carbamate-cyclofructan 6 (IP-CF6), (R)-naphthylethylcarbamate cyclofructan 6 (RN-CF6), or dimethylphenylcarbamate cyclofructan 7 (DMP-CF7) as chiral selectors, using n-hexane/alcohol/TFA as mobile phase. The effects of the mobile phase composition, the nature and concentrations of the alcoholic and acidic modifiers, and the structures of the analytes on the retention and resolution were investigated. In some cases, separations were carried out at constant mobile phase composition in the temperature range 540 degrees C. Thermodynamic parameters and Tiso values were calculated from plots of lnk versus 1/T. It was found that the enantioseparations were enthalpy driven. The sequences of elution of the stereoisomers were determined but no general rule could be established. LA - English DB - MTMT ER - TY - JOUR AU - Sipos, László AU - Ilisz, István AU - Aranyi, Anita AU - Gecse, Zsanett AU - Nonn, Melinda AU - Fülöp, Ferenc AU - Ho, Hyun Myung AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phases JF - CHIRALITY: THE PHARMACOLOGICAL BIOLOGICAL AND CHEMICAL CONSEQUENCES OF MOLECULAR ASYMMETRY J2 - CHIRALITY VL - 24 PY - 2012 IS - 10 SP - 817 EP - 824 PG - 8 SN - 0899-0042 DO - 10.1002/chir.22077 UR - https://m2.mtmt.hu/api/publication/1949178 ID - 1949178 N1 - Funding Agency and Grant Number: Hungarian National Science Foundation [K 67563] Funding text: Contract grant sponsor: Hungarian National Science Foundation; Contract grant number: K 67563. ISSN:0899-0042 AB - The enantiomers of four unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids were directly separated on chiral stationary phases containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The nature of the alcoholic modifier (MeOH, EtOH, IPA) exerted a great effect on the retention, whereas the selectivity and resolution did not change substantially. Two types of dependence of retention on alcohol content were detected: k1 increased continuously with increasing alcohol content or a U-shaped retention curve was observed. A comparison of the chromatographic data obtained with HCOOH, AcOH, TFA, HClO4, H2SO4, or H3PO4 as acidic modifier at a constant concentration demonstrated that in most cases, larger k values were obtained on the application of AcOH or HCOOH, and an increase of the acid content resulted in a decrease of retention. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes and selector. The sequence of elution of the enantiomers was determined in all cases. Chirality 24:817-824, 2012. (c) 2012 Wiley Periodicals, Inc. LA - English DB - MTMT ER -