@article{MTMT:2459240, title = {Foldameric α/β-Peptide Analogs of the β-Sheet-Forming Antiangiogenic Anginex: Structure and Bioactivity}, url = {https://m2.mtmt.hu/api/publication/2459240}, author = {Hegedüs, Zsófia and Wéber, Edit and Kriston-Pál, Éva and Makra, Ildikó and Czibula, Ágnes and Monostori, Éva and Martinek, Tamás}, doi = {10.1021/ja408054f}, journal-iso = {J AM CHEM SOC}, journal = {JOURNAL OF THE AMERICAN CHEMICAL SOCIETY}, volume = {135}, unique-id = {2459240}, issn = {0002-7863}, abstract = {The principles of beta-sheet folding and design for alpha-peptidic sequences are well established, while those for sheet mimetics containing homologated amino acid building blocks are still under investigation. To reveal the structure-function relations of beta-amino-acid-containing foldamers, we followed a top-down approach to study a series of alpha/beta-peptidic analogs of anginex, a beta-sheet-forming antiangiogenic peptide. Eight anginex analogs were developed by systematic alpha --> beta(3) substitutions and analyzed by using NMR and CD spectroscopy. The foldamers retained the beta-sheet tendency, though with a decreased folding propensity. beta-Sheet formation could be induced by a micellar environment, similarly to that of the parent peptide. The destructuring effect was higher when the alpha --> beta(3) exchange was located in the beta-sheet core. Analysis of the beta-sheet stability versus substitution pattern and the local conformational bias of the bulky beta(3)V and beta(3)I residues revealed that a mismatch between the H-bonding preferences of the alpha- and beta-residues played a minor role in the structure-breaking effect. Temperature-dependent CD and NMR measurements showed that the hydrophobic stabilization was scaled-down for the alpha/beta-peptides. Analysis of the biological activity of the foldamer peptides showed that four anginex derivatives dose-dependently inhibited the proliferation of a mouse endothelial cell line. The alpha --> beta(3) substitution strategy applied in this work can be a useful approach to the construction of bioactive beta-sheet mimetics with a reduced aggregation tendency and improved pharmacokinetic properties.}, year = {2013}, eissn = {1520-5126}, pages = {16578-16584}, orcid-numbers = {Hegedüs, Zsófia/0000-0002-5546-8167; Wéber, Edit/0000-0002-5904-0619; Czibula, Ágnes/0000-0003-4461-2773; Monostori, Éva/0000-0002-7442-3562; Martinek, Tamás/0000-0003-3168-8066} } @article{MTMT:1819649, title = {High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on macrocyclic glycopeptide-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/1819649}, author = {Sipos, László and Ilisz, István and Nonn, Melinda and Fülöp, Ferenc and Pataj, Zoltán and Armstrong, D W and Péter, Antal}, doi = {10.1016/j.chroma.2011.11.027}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1232}, unique-id = {1819649}, issn = {0021-9673}, year = {2012}, eissn = {1873-3778}, pages = {142-151}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Nonn, Melinda/0000-0002-1623-4173; 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} } @article{MTMT:1321220, title = {High-performance liquid chromatographic enantioseparation of β2-amino acids using a long-tethered (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase}, url = {https://m2.mtmt.hu/api/publication/1321220}, author = {Ilisz, István and Pataj, Zoltán and Berkecz, Róbert and Misicka, A and Tymecka, D and Fülöp, Ferenc and Choi, HJ and Hyun, MH and Péter, Antal}, doi = {10.1016/j.chroma.2009.07.003}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1217}, unique-id = {1321220}, issn = {0021-9673}, abstract = {Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural [beta]2-amino acids on a new chiral stationary phase, using the 11-methylene-unit spacer of aminoundecylsilica gel for the bonding of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as selector. The nature and concentration of the acidic and organic modifiers, the pH, the mobile phase composition, and the structures of the analytes substantially influenced the retention and resolution. Separations were carried out at constant mobile phase compositions in the temperature range 7-40 °C and the changes in enthalpy, [Delta]([Delta]H°), entropy, [Delta]([Delta]S°), and free energy, [Delta]([Delta]G°) were calculated. The elution sequence was determined in some cases: the S enantiomers eluted before the R enantiomers.}, year = {2010}, eissn = {1873-3778}, pages = {1075-1082}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Berkecz, Róbert/0000-0002-9076-2177; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1189444, title = {High-performance liquid chromatographic enantioseparation of 2-aminomono- and dihydroxycyclopentanecarboxylic and 2-aminodihydroxycyclohexanecarboxylic acids on macrocyclic glycopeptide-based phases}, url = {https://m2.mtmt.hu/api/publication/1189444}, author = {Berkecz, Róbert and Ilisz, István and Benedek, G and Fülöp, Ferenc and Armstrong, DW and Péter, Antal}, doi = {10.1016/j.chroma.2008.12.011}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1216}, unique-id = {1189444}, issn = {0021-9673}, abstract = {The direct separation of the enantiomers of four 2-aminomono- or dihydroxycyclopentanecarboxylic acids and four 2-aminodihydroxycyclohexanecarboxylic acids was performed on chiral stationary phases containing macrocyclic glycopeptide antibiotics such as teicoplanin (Astec Chirobiotic T and T2), teicoplanin aglycone (Chirobiotic TAG) or ristocetin A (Chirobiotic R) as chiral selectors. The effects of the nature of organic modifiers, the pH, the mobile phase composition and the structures of the analytes oil the separation were investigated. Chirobiotic TAG, and in some cases Chirobiotic T, proved to be the Most useful of these columns. The elution sequence was determined in most cases. (C) 2008 Elsevier B.V. All rights reserved.}, year = {2009}, eissn = {1873-3778}, pages = {927-932}, orcid-numbers = {Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1230499, title = {HPLC enantioseparation of beta(2)-homoamino acids using crown ether-based chiral stationary phase}, url = {https://m2.mtmt.hu/api/publication/1230499}, author = {Berkecz, Róbert and Ilisz, István and Misicka, A and Tymecka, D and Fülöp, Ferenc and Choi, HJ and Hyun, MH and Péter, Antal}, doi = {10.1002/jssc.200800561}, journal-iso = {J SEP SCI}, journal = {JOURNAL OF SEPARATION SCIENCE}, volume = {32}, unique-id = {1230499}, issn = {1615-9306}, abstract = {RP high-performance liquid chromatographic methods were developed for the enantioseparation of eleven unusual beta(2)-homoamino acids. The underivatized analytes were separated on a chiral stationary phase containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The effects of organic (alcoholic) and acidic modifiers, the mobile phase composition and temperature on the separation were investigated. The structures of the substituents in the alpha-position of the analytes substantially influenced the retention and resolution. The elution sequence was determined in some cases: the S enantiomers eluted before the R enantiomers.}, year = {2009}, eissn = {1615-9314}, pages = {981-987}, orcid-numbers = {Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1122999, title = {High-performance liquid chromatographic enantioseparation of beta-3-homo-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase}, url = {https://m2.mtmt.hu/api/publication/1122999}, author = {Berkecz, Róbert and Ilisz, István and Fülöp, Ferenc and Pataj, Zoltán and Hyun, MH and Péter, Antal}, doi = {10.1016/j.chroma.2007.09.054}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1189}, unique-id = {1122999}, issn = {0021-9673}, abstract = {High-performance liquid chromatographic methods were developed for the separation of the enantiomers of thirteen unusual beta-3-homo-amino acids and three of its ethyl esters on a chiral stationary phase containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The effects of the mobile phase composition and the acidic modifiers on the separation were investigated. The structures of the substiments in beta-position substantially influenced the retention and enantioseparation. The influence of ionic strength. on the enantioseparation was established experimentally. The elution sequence was determined in all cases. (c) 2007 Elsevier B.V. All rights reserved.}, year = {2008}, eissn = {1873-3778}, pages = {285-291}, orcid-numbers = {Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1127901, title = {New endomorphin analogues containing alicyclic beta-amino acids: Influence on bioactive conformation and pharmacological profile}, url = {https://m2.mtmt.hu/api/publication/1127901}, author = {Keresztes, Attila and Szűcs, Mária and Borics, Attila and E Kövér, Katalin and Forró, Enikő and Fülöp, Ferenc and Tömböly, Csaba and Péter, Antal and Pahi, A and Fábián, Gabriella and Muranyi, M and Tóth, Géza}, doi = {10.1021/jm800223t}, journal-iso = {J MED CHEM}, journal = {JOURNAL OF MEDICINAL CHEMISTRY}, volume = {51}, unique-id = {1127901}, issn = {0022-2623}, abstract = {Endomorphins were subjected to a number of structural modifications in a search for their bioactive conformations. The alicyclic beta-amino acids cis-(1S,2R)ACPC/ACHC, cis-(IR,2S)ACPC/ACHC, trans(IS,2S)ACPC/ACHC, and trans-(1R,2R)ACPC/ACHC were introduced into endomorphins to examine the conformational effects on the bioactivity. Use of a combination of receptor binding techniques, H-1 NMR, and molecular modeling allowed the conclusion that Pro(2) substitution by these residues causes changes in structure, proteolytic stability, and pharmacological activity. It seems that the size of the alicyclic beta-amino acids does not have marked influence on the receptor binding affinities and/or selectivities. Among the new analogues, the cis-(1S,2R)ACPC(2) and cis-(1S,2R)ACHC(2)-containing derivatives displayed the highest binding potencies and efficacies in receptor binding and ligand-stimulated [S-35]GTP gamma S functional experiments. Molecular dynamic simulations and H-1 NMR studies of the cis-ACPC/ACHC-containing analogues revealed that many conformations are accessible, though it is most likely that these peptides bind to the mu-opioid receptor in a compact, folded structure rather than extended.}, year = {2008}, eissn = {1520-4804}, pages = {4270-4279}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287; Fábián, Gabriella/0000-0002-2323-4948} } @article{MTMT:1916846, title = {Beta-homo-amino acid scan of angiotensin IV}, url = {https://m2.mtmt.hu/api/publication/1916846}, author = {Lukaszuk, A and Demaegdt, H and Szemenyei, Erzsébet and Tóth, Géza and Tymecka, D and Misicka, A and Karoyan, P and Vanderheyden, P and Vauquelin, G and Tourwe, D}, doi = {10.1021/jm701490g}, journal-iso = {J MED CHEM}, journal = {JOURNAL OF MEDICINAL CHEMISTRY}, volume = {51}, unique-id = {1916846}, issn = {0022-2623}, abstract = {Angiotensin IV, a metabolite of angiotensin II, inhibits the enzyme insulin regulated aminopeptidase or IRAP and also, although with lower potency, aminopeptidase-N (AP-N). When both beta(2)-homo amino acid- and beta(3)-homo amino acid substitutions were used, allowed the identification of H-(R) beta(2)hVal-Tyr-Ile-His-Pro-beta(3) hPhe-OH as a potent and stable Ang IV analog with high selectivity for IRAP versus AP-N and the AT1 receptor.}, year = {2008}, eissn = {1520-4804}, pages = {2291-2296} } @article{MTMT:1078949, title = {High-performance liquid chromatographic enantioseparation of beta-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase}, url = {https://m2.mtmt.hu/api/publication/1078949}, author = {Berkecz, Róbert and Sztojkov-Ivanov, Anita and Ilisz, István and Forró, Enikő and Fülöp, Ferenc and Hyun, MH and Péter, Antal}, doi = {10.1016/j.chroma.2006.06.064}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1125}, unique-id = {1078949}, issn = {0021-9673}, year = {2006}, eissn = {1873-3778}, pages = {138-143}, orcid-numbers = {Berkecz, Róbert/0000-0002-9076-2177; Ilisz, István/0000-0001-8282-457X; Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1323957, title = {HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic-based chiral stationary phases: A review}, url = {https://m2.mtmt.hu/api/publication/1323957}, author = {Ilisz, István and Berkecz, Róbert and Péter, Antal}, doi = {10.1002/jssc.200600046}, journal-iso = {J SEP SCI}, journal = {JOURNAL OF SEPARATION SCIENCE}, volume = {29}, unique-id = {1323957}, issn = {1615-9306}, keywords = {HPLC; MASS-SPECTROMETRY; amino acids; enantiomer separation; RISTOCETIN-A; LIQUID-CHROMATOGRAPHIC SEPARATION; TAG COLUMNS; CHIROBIOTIC-T; GLYCOPEPTIDES; MOBILE-PHASE; ENANTIOSELECTIVE SEPARATION; SELENOMETHIONINE ENANTIOMERS; BONDED TEICOPLANIN COLUMNS; CAPILLARY ELECTROPHORETIC ENANTIOSEPARATIONS; microcyclic antibiotics}, year = {2006}, eissn = {1615-9314}, pages = {1305-1321}, orcid-numbers = {Ilisz, István/0000-0001-8282-457X; Berkecz, Róbert/0000-0002-9076-2177} } @article{MTMT:1013257, title = {Direct and indirect high-performance liquid chromatographic enantioseparation of beta-amino acids}, url = {https://m2.mtmt.hu/api/publication/1013257}, author = {Péter, Antal and Arki, A and Vekes, E and Tourwe, D and Lázár, László and Fülöp, Ferenc and Armstrong, D W}, doi = {10.1016/j.chroma.2003.08.070}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1031}, unique-id = {1013257}, issn = {0021-9673}, keywords = {PEPTIDES; RESOLUTION; ENANTIOMERS; SEPARATION; amino acids; derivatization, LC; enantiomer separation; CHIRAL STATIONARY-PHASE; DERIVATIZING AGENT; nitrophenoxycarbonyl phenylalanine methoxyethyl ester; stationary phases, LC; LIGAND-EXCHANGE CHROMATOGRAPHY}, year = {2004}, eissn = {1873-3778}, pages = {171-178}, orcid-numbers = {Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1322892, title = {Liquid chromatographic enantioseparation of spin-labelled beta-amino acids}, url = {https://m2.mtmt.hu/api/publication/1322892}, author = {Péter, Antal and Torok, R and Wright, K and Wakselman, M and Mazaleyrat, JP}, doi = {10.1016/j.chroma.2003.09.015}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1021}, unique-id = {1322892}, issn = {0021-9673}, year = {2003}, eissn = {1873-3778}, pages = {1-10} } @article{MTMT:1322901, title = {Direct high-performance liquid chromatographic enantioseparation of apolar beta-amino acids on a quinine-derived chiral anion-exchanger stationary phase}, url = {https://m2.mtmt.hu/api/publication/1322901}, author = {Péter, Antal}, doi = {10.1016/S0021-9673(02)00192-9}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {955}, unique-id = {1322901}, issn = {0021-9673}, year = {2002}, eissn = {1873-3778}, pages = {141-150} } @article{MTMT:1322900, title = {Effects of temperature on retention of chiral compounds on a ristocetin A chiral stationary phase}, url = {https://m2.mtmt.hu/api/publication/1322900}, author = {Péter, Antal and Vekes, E and Armstrong, DW}, doi = {10.1016/S0021-9673(02)00390-4}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {958}, unique-id = {1322900}, issn = {0021-9673}, year = {2002}, eissn = {1873-3778}, pages = {89-107} } @article{MTMT:1013893, title = {High-performance liquid chromatographic enantioseparation of beta-amino acids}, url = {https://m2.mtmt.hu/api/publication/1013893}, author = {Péter, Antal and Lázár, László and Fülöp, Ferenc and Armstrong, D W}, doi = {10.1016/S0021-9673(01)01078-0}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {926}, unique-id = {1013893}, issn = {0021-9673}, abstract = {Direct and indirect high-performance liquid chromatographic methods were developed for the enantioseparation of beta -amino acids (beta -substituted- beta -alanines). Direct separation involved the application of chiral columns: Crownpak CR(+), Chirobiotic T and Chirobiotic R. Indirect separation was based on precolumn derivatization with 2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl isothiocyanate or N-alpha-(2,4-dinitro-5-fluorophenyl)-L-alanineamide (Marfey's reagent), with subsequent separation on an achiral column. The chromatographic conditions were varied to achieve optimum separation.}, year = {2001}, eissn = {1873-3778}, pages = {229-238}, orcid-numbers = {Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1322919, title = {Effect of temperature on retention of enantiomers of beta-methyl amino acids on a teicoplanin chiral stationary phase}, url = {https://m2.mtmt.hu/api/publication/1322919}, author = {Péter, Antal and Torok, G and Armstrong, DW and Tóth, Géza and Tourwe, D}, doi = {10.1016/S0021-9673(98)00835-8}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {828}, unique-id = {1322919}, issn = {0021-9673}, year = {1998}, eissn = {1873-3778}, pages = {177-190} }