TY - JOUR AU - Orsy, György AU - Forró, Enikő TI - Lipase-Catalyzed Strategies for the Preparation of Enantiomeric THIQ and THβC Derivatives: Green Aspects JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 17 PG - 14 SN - 1420-3049 DO - 10.3390/molecules28176362 UR - https://m2.mtmt.hu/api/publication/34123133 ID - 34123133 N1 - Export Date: 20 September 2023 CODEN: MOLEF Correspondence Address: Forró, E.; Institute of Pharmaceutical Chemistry, Eötvös u. 6, Hungary; email: forro.eniko@szte.hu Funding details: Hungarian Scientific Research Fund, OTKA, K-138871 Funding details: Emberi Eroforrások Minisztériuma, EMMI, TKP-2021-EGA-32 Funding text 1: The authors’ thanks are due to the Hungarian Research Foundation (OTKA No. K-138871) and the Ministry of Human Capacities, Hungary, grant TKP-2021-EGA-32. AB - This report reviews the most important lipase-catalyzed strategies for the preparation of pharmaceutically and chemically important tetrahydroisoquinoline and tetrahydro-β-carboline enantiomers through O-acylation of the primary hydroxy group, N-acylation of the secondary amino group, and COOEt hydrolysis of the corresponding racemic compounds with simple molecular structure, which have been reported during the last decade. A brief introduction describes the importance and synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline derivatives, and it formulates the objectives of this compilation. The strategies are presented in chronological order, classified according to function of the reaction type, as kinetic and dynamic kinetic resolutions, in the main text. These reactions result in the desired products with excellent ee values. The pharmacological importance of the products together with their synthesis is given in the main text. The enzymatic hydrolysis of the hydrochloride salts as racemates of the starting amino carboxylic esters furnished the desired enantiomeric amino carboxylic acids quantitatively. The enzymatic reactions, performed in tBuOMe or H2O as usable solvents, and the transformations carried out in a continuous-flow system, indicate clear advantages, including atom economy, reproducibility, safer solvents, short reaction time, rapid heating and compression vs. shaker reactions. These features are highlighted in the main text. LA - English DB - MTMT ER - TY - JOUR AU - Orsy, György AU - Shahmohammadi, Sayeh AU - Forró, Enikő TI - A Sustainable Green Enzymatic Method for Amide Bond Formation JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 15 PG - 11 SN - 1420-3049 DO - 10.3390/molecules28155706 UR - https://m2.mtmt.hu/api/publication/34082152 ID - 34082152 N1 - Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Stereochemistry Research Group, Eötvös Loránd Research Network, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Export Date: 28 August 2023 CODEN: MOLEF Correspondence Address: Forró, E.; Institute of Pharmaceutical Chemistry, Eötvös u. 6, Hungary; email: forro.eniko@szte.hu Funding details: TKP-2021-EGA-32 Funding details: Hungarian Scientific Research Fund, OTKA, K-138871 Funding text 1: The authors’ thanks are due to the Hungarian Research Foundation (OTKA No. K-138871), the Ministry of Human Capacities, Hungary (grant TKP-2021-EGA-32). AB - A sustainable enzymatic strategy for the preparation of amides by using Candida antarctica lipase B as the biocatalyst and cyclopentyl methyl ether as a green and safe solvent was devised. The method is simple and efficient and it produces amides with excellent conversions and yields without the need for intensive purification steps. The scope of the reaction was extended to the preparation of 28 diverse amides using four different free carboxylic acids and seven primary and secondary amines, including cyclic amines. This enzymatic methodology has the potential to become a green and industrially reliable process for direct amide synthesis. LA - English DB - MTMT ER - TY - CONF AU - Shahmohammadi, Sayeh AU - Faragó, Tünde AU - Palkó, Márta AU - Forró, Enikő TI - Green enzymatic strategies for the preparation of enantiomeric carbocyclic beta-amino acid derivatives T2 - GreenCat 2022 Book of Abstracts PY - 2022 PG - 1 UR - https://m2.mtmt.hu/api/publication/33672957 ID - 33672957 LA - English DB - MTMT ER - TY - CHAP AU - Tanács, Dániel AU - Berkecz, Róbert AU - Shahmohammadi, Sayeh AU - Forró, Enikő AU - Daniel, W. Armstrong AU - Péter, Antal AU - Ilisz, István ED - Felinger, Attila TI - Liquid Chromatographic Enantioseparation of Fluorinated ß-Phenylalanine Analogs Utilizing Superficially Porous Particles T2 - 33rd International Symposium on Chromatography – ISC 2022 PB - Hungarian Society for Separation Sciences CY - Budapest SN - 9786155270741 PY - 2022 PG - 1 UR - https://m2.mtmt.hu/api/publication/33551486 ID - 33551486 LA - English DB - MTMT ER - TY - JOUR AU - Forró, Enikő AU - Fülöp, Ferenc TI - Enzymatic Strategies for the Preparation of Pharmaceutically Important Amino Acids through Hydrolysis of Amino Carboxylic Esters and Lactams JF - CURRENT MEDICINAL CHEMISTRY J2 - CURR MED CHEM VL - 29 PY - 2022 IS - 41 SP - 6218 EP - 6227 PG - 10 SN - 0929-8673 DO - 10.2174/0929867329666220718123153 UR - https://m2.mtmt.hu/api/publication/33025006 ID - 33025006 N1 - Funding Agency and Grant Number: Hungarian Scientific Research Council (OTKA) [K129049]; Ministry of National Economy, National Research, Development and Innovation Office (GINOP) [2.3.2-15-2016-00014]; ITM NKFIA [TKP2021-EGA-32] Funding text: The authors thank the Hungarian Scientific Research Council (OTKA, K129049) and the Ministry of National Economy, National Research, Development and Innovation Office (GINOP, 2.3.2-15-2016-00014) and ITM NKFIA TKP2021-EGA-32 for financial support. LA - English DB - MTMT ER - TY - JOUR AU - Tanács, Dániel AU - Berkecz, Róbert AU - Shahmohammadi, Sayeh AU - Forró, Enikő AU - Armstrong, Daniel W. AU - Péter, Antal AU - Ilisz, István TI - Macrocyclic glycopeptides- and derivatized cyclofructan-based chiral stationary phases for the enantioseparation of fluorinated ß-phenylalanine analogs JF - JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS J2 - J PHARMACEUT BIOMED ANAL VL - 219 PY - 2022 PG - 9 SN - 0731-7085 DO - 10.1016/j.jpba.2022.114912 UR - https://m2.mtmt.hu/api/publication/32936379 ID - 32936379 N1 - Funding Agency and Grant Number: National Research, Development and Innovation Office-NKFIA [K137607, K129049, TKP2021-EGA-32]; Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund [TKP2021-EGA] Funding text: Acknowledgments 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 - Shahmohammadi, Sayeh AU - Faragó, Tünde AU - Palkó, Márta AU - Forró, Enikő TI - Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis JF - MOLECULES J2 - MOLECULES VL - 27 PY - 2022 IS - 8 PG - 11 SN - 1420-3049 DO - 10.3390/molecules27082600 UR - https://m2.mtmt.hu/api/publication/32787510 ID - 32787510 N1 - Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, Faculty of Pharmacy, University of Szeged, Szeged, H-6720, Hungary MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Szeged, H-6720, Hungary Export Date: 4 June 2023 CODEN: MOLEF Correspondence Address: Forró, E.; Institute of Pharmaceutical Chemistry, Hungary; email: forro.eniko@szte.hu Chemicals/CAS: amino acid, 65072-01-7; Amino Acids; Esters; Fungal Proteins; Solvents Funding details: 2.3.2-15-2016-00014, EFOP 3.6.3-VEKOP-16-2017-00009 Funding details: Hungarian Scientific Research Fund, OTKA, K129049, K138871 Funding details: National Research, Development and Innovation Office Funding text 1: Funding: The authors thank the Hungarian Scientific Research Council (OTKA, K129049 and K138871) and the Ministry of National Economy, National Research, Development and Innovation Office (GINOP, 2.3.2-15-2016-00014) and (EFOP 3.6.3-VEKOP-16-2017-00009) for financial support. 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 - Bajtai, Attila AU - Berkecz, Róbert AU - Forró, Enikő AU - Fülöp, Ferenc AU - Lindner, Wolfgang AU - Péter, Antal AU - Ilisz, István TI - Cinchona-alkaloid-based zwitterionic chiral stationary phases as potential tools for high-performance liquid chromatographic enantioseparation of cationic compounds of pharmaceutical relevance JF - JOURNAL OF SEPARATION SCIENCE J2 - J SEP SCI VL - 44 PY - 2021 IS - 14 SP - 2735 EP - 2743 PG - 9 SN - 1615-9306 DO - 10.1002/jssc.202100264 UR - https://m2.mtmt.hu/api/publication/32069177 ID - 32069177 N1 - Institute of Pharmaceutical Analysis, Interdisciplinary Excellence Centre, University of Szeged, Szeged, Hungary Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, Szeged, Hungary Department of Analytical Chemistry, University of Vienna, Vienna, Austria Export Date: 7 September 2021 CODEN: JSSCC Correspondence Address: Ilisz, I.; Institute of Pharmaceutical Analysis, Hungary; email: ilisz.istvan@szte.hu Funding details: TKP‐2020 Funding details: Hungarian Scientific Research Fund, OTKA, K129049 Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH Funding details: Innovációs és Technológiai Minisztérium Funding text 1: This work was supported by the project grant GINOP‐2.3.2‐15‐2016‐00034 by the National Research Development and Innovation Office, and the ÚNKP‐20‐3 New National Excellence Program of the Ministry for Innovation and Technology from the Source of National Research, Development and Innovation Fund. The Ministry of Human Capacities, Hungary grant TKP‐2020 and the grant of Hungarian Scientific Research Council (OTKA, K129049) is also acknowledged. LA - English DB - MTMT ER - TY - JOUR AU - Bajtai, Attila AU - Tanács, Dániel AU - Berkecz, Róbert AU - Forró, Enikő AU - Fülöp, Ferenc AU - Lindner, Wolfgang AU - Péter, Antal AU - Ilisz, István TI - High-performance liquid chromatographic evaluation of strong cation exchanger-based chiral stationary phases focusing on stationary phase characteristics and mobile phase effects employing enantiomers of tetrahydro-ß-carboline and 1,2,3,4-tetrahydroisoquinoline analogs JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1644 PY - 2021 PG - 9 SN - 0021-9673 DO - 10.1016/j.chroma.2021.462121 UR - https://m2.mtmt.hu/api/publication/31959792 ID - 31959792 LA - English DB - MTMT ER -