@article{MTMT:31625419, title = {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}, url = {https://m2.mtmt.hu/api/publication/31625419}, author = {Pálinkás, Noémi and Mikle, Gábor and Aranyi, Anita and Péter, Antal and Kollár, László}, doi = {10.1002/slct.202002093}, journal-iso = {CHEMISTRYSELECT}, journal = {CHEMISTRYSELECT}, volume = {5}, unique-id = {31625419}, issn = {2365-6549}, abstract = {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.}, keywords = {COMPLEXES; carbon monoxide; FACILE SYNTHESIS; Carbonylation; Carbonylation; Carboxamide; Axial chirality}, year = {2020}, eissn = {2365-6549}, pages = {11048-11051} } @article{MTMT:2869802, title = {Exploring the enantioseparation of amino-naphthol analogues by supercritical fluid chromatography}, url = {https://m2.mtmt.hu/api/publication/2869802}, author = {Aranyi, Anita and Ilisz, István and Péter, Antal and Fülöp, Ferenc and West, C}, doi = {10.1016/j.chroma.2015.01.084}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1387}, unique-id = {2869802}, issn = {0021-9673}, abstract = {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.}, keywords = {CHROMATOGRAPHY; METHANOL; IMMOBILIZATION; ARTICLE; WATER; AMMONIA; priority journal; controlled study; Acetic Acid; Carbon Dioxide; CHIRALITY; unclassified drug; ADDITIVES; enantioseparation; ENANTIOSELECTIVITY; CHIRAL STATIONARY PHASES; Betti bases; Gas chromatography; silica gel; separation technique; process optimization; enantiomer; SUPERCRITICAL FLUIDS; Trifluoroacetic Acid; Chiral stationary phasis; polysaccharide; racemic mixture; temperature sensitivity; elution; Phase separation; DICHLOROMETHANE; 2 propanol; Organic solvents; ammonium acetate; effluent treatment; Ethanolamines; triethylamine; formic acid; triethanolamine; diethylamine; cellulose tris(3,5 dimethylphenylcarbamate); Supercritical fluid chromatography; NAPHTHOL; 1 naphthol derivative; deanol; diethanolamine; cellulose tris(3,5 dichlorophenylcarbamate); amylose tris(3,5 dichlorophenylcarbamate); amylose tris(3 chlorophenylcarbamate); 2 (alpha aminoarylmethyl) 1 naphthol derivative; 2 (1 amino 2 methylpropyl) 1 naphthol; 1 naphthol; 1 (alpha aminoarylmethyl) 2 naphthol derivative; 1 (alpha aminoalkyl) 2 naphthol derivative; Super critical fluid chromatography; Naphthol derivatives; Mobile phase additives; Elution conditions; Column temperature; Immobilized polysaccharide}, year = {2015}, eissn = {1873-3778}, pages = {123-133}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Fülöp, Ferenc/0000-0003-1066-5287} } @mastersthesis{MTMT:2818947, title = {Poliszacharid és ciklofruktán típusú királis állófázisok alkalmazása enantiomerek elválasztására}, url = {https://m2.mtmt.hu/api/publication/2818947}, author = {Aranyi, Anita}, doi = {10.14232/phd.2356}, publisher = {SZTE}, unique-id = {2818947}, year = {2014} } @article{MTMT:2790838, title = {Aminonaftol enantiomerek nagyhatékonyságú folyadékkromatográfiás vizsgálata: A hőmérséklet hatása a királis elválasztásra}, url = {https://m2.mtmt.hu/api/publication/2790838}, author = {Aranyi, Anita and Pataj, Zoltán and Ilisz, István and Péter, Antal}, journal-iso = {MAGY KÉM FOLY KÉM KÖZL}, journal = {MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-)}, volume = {120}, unique-id = {2790838}, issn = {1418-9933}, year = {2014}, eissn = {1418-8600}, pages = {60-66}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X} } @article{MTMT:2790835, title = {Nagyhatékonyságú folyadékkromatográfiás enantiomerelválasztás: ß-aminosavak viselkedése antibiotikum szelektorokon}, url = {https://m2.mtmt.hu/api/publication/2790835}, author = {Pataj, Zoltán and Aranyi, Anita and Ilisz, István and Péter, Antal}, journal-iso = {MAGY KÉM FOLY KÉM KÖZL}, journal = {MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-)}, volume = {120}, unique-id = {2790835}, issn = {1418-9933}, year = {2014}, eissn = {1418-8600}, pages = {45-49}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X} } @article{MTMT:2770770, title = {Cyclodextrin-mediated enantioseparation of phenylalanine amide derivatives and amino alcohols by capillary electrophoresis-Role of complexation constants and complex mobilities}, url = {https://m2.mtmt.hu/api/publication/2770770}, author = {Aranyi, Anita and Péter, Antal and Ilisz, István and Fülöp, Ferenc and Scriba, GKE}, doi = {10.1002/elps.201400142}, journal-iso = {ELECTROPHORESIS}, journal = {ELECTROPHORESIS}, volume = {35}, unique-id = {2770770}, issn = {0173-0835}, abstract = {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.}, keywords = {enantiomer separation; Binding constants; Phenylalanine amide; Highly sulfated cyclodextrin; Amino alcohol}, year = {2014}, eissn = {1522-2683}, pages = {2848-2854}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:2547618, title = {Enantioseparation of β2-amino acids on cinchona alkaloid-based zwitterionic chiral stationary phases. Structural and temperature effects}, url = {https://m2.mtmt.hu/api/publication/2547618}, author = {Ilisz, István and Grecsó, Nóra and Aranyi, Anita and Suchotin, P and Tymecka, D and Wilenska, B and Misicka, A and Fülöp, Ferenc and Lindner, W and Péter, Antal}, doi = {10.1016/j.chroma.2014.01.075}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1334}, unique-id = {2547618}, issn = {0021-9673}, abstract = {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.}, keywords = {liquid chromatography; Temperature dependence of enantioseparation; Quinine- and quinidine-based chiral zwitterionic ion-exchanger selectors; β2-Amino acids}, year = {2014}, eissn = {1873-3778}, pages = {44-54}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Grecsó, Nóra/0000-0003-4323-1872; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:2238778, title = {Development of the high-performance liquid chromatographic method for the enantioseparation of unusual glycine ester analogs on polysaccharide-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/2238778}, author = {Aranyi, Anita and Ilisz, István and Grecsó, Nóra and Csütörtöki, Renáta and Szatmári, István and Fülöp, Ferenc and Péter, Antal}, doi = {10.1016/j.jpba.2012.12.030}, journal-iso = {J PHARMACEUT BIOMED ANAL}, journal = {JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS}, volume = {76}, unique-id = {2238778}, issn = {0731-7085}, abstract = {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.}, keywords = {DERIVATIVES; SELECTIVITY; ENANTIOMERS; AMYLOSE; pharmaceuticals; enantiomer separation; column liquid chromatography; 2-(alpha-aminobenzyl)-1-naphthol analogs; 1-(ALPHA-AMINOBENZYL)-2-NAPHTHOL; REVERSE-TRANSCRIPTASE INHIBITORS; IMMOBILIZED CELLULASE; Lux Amylose-2 column; EFAVIRENZ SUSTIVA(TM); Lux Cellulose columns; Gly analogs}, year = {2013}, eissn = {1873-264X}, pages = {183-191}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Grecsó, Nóra/0000-0003-4323-1872; Szatmári, István/0000-0002-8571-5229; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:2046793, title = {High-performance liquid chromatographic enantioseparation of amino compounds on newly developed cyclofructan-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/2046793}, author = {Aranyi, Anita and Bagi, Ágnes and Ilisz, István and Pataj, Zoltán and Fülöp, Ferenc and Armstrong, DW and Péter, Antal}, doi = {10.1002/jssc.201100921}, journal-iso = {J SEP SCI}, journal = {JOURNAL OF SEPARATION SCIENCE}, volume = {35}, unique-id = {2046793}, issn = {1615-9306}, abstract = {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.}, keywords = {enantioseparation; column liquid chromatography; temperature effect; IMMOBILIZED CELLULASE; ASYMMETRIC TRANSFER HYDROGENATION; aldol reactions; Cyclofructan-based columns; Amino compounds}, year = {2012}, eissn = {1615-9314}, pages = {617-624}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1949178, title = {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}, url = {https://m2.mtmt.hu/api/publication/1949178}, author = {Sipos, László and Ilisz, István and Aranyi, Anita and Gecse, Zsanett and Nonn, Melinda and Fülöp, Ferenc and Ho, Hyun Myung and Péter, Antal}, doi = {10.1002/chir.22077}, journal-iso = {CHIRALITY}, journal = {CHIRALITY: THE PHARMACOLOGICAL BIOLOGICAL AND CHEMICAL CONSEQUENCES OF MOLECULAR ASYMMETRY}, volume = {24}, unique-id = {1949178}, issn = {0899-0042}, abstract = {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.}, keywords = {enantiomer separation; column liquid chromatography; Isoxazoline-fused 2-Aminocyclopentanecarboxylic acids; 3; (+)-(18-crown-6)-2; 11; 12-tetracarboxylic acid-based chiral stationary phases}, year = {2012}, eissn = {1520-636X}, pages = {817-824}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Nonn, Melinda/0000-0002-1623-4173; Fülöp, Ferenc/0000-0003-1066-5287} }