TY - JOUR AU - Forró, Enikő AU - Fülöp, Ferenc TI - Advanced procedure for the enzymatic ring opening of unsaturated alicyclic beta-lactams JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 15 PY - 2004 IS - 18 SP - 2875 EP - 2880 PG - 6 SN - 0957-4166 DO - 10.1016/j.tetasy.2004.05.029 UR - https://m2.mtmt.hu/api/publication/1013238 ID - 1013238 N1 - Cited By :65 Export Date: 3 June 2023 CODEN: TASYE Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, , Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu Chemicals/CAS: chloride, 16887-00-6; water, 7732-18-5 Funding details: Hungarian Scientific Research Fund, OTKA, 0115/2001, 181/2002, T 046440, TS 040888 Funding text 1: The authors acknowledge the receipt of OTKA grants TS 040888 and T 046440, FKFP grant 0115/2001 and a Békésy Fellowship for EF (grant no. 181/2002). AB - Enantiopure beta-amino acids 1a-4a and beta-lactams 1b-4b were prepared simultaneously through the lipolase-catalysed enantioselective ring opening of unsaturated racemic beta-lactams (+/-)-1-(+/-)-4. High enantioselectivities (E >200) were observed when the reactions were performed with 1 equiv of water in iPr(2)O at 70degreesC. The resolved (1R,2S)-amino acids (yield greater than or equal to 45%) and (1S,5R)-, (1S,6R)- and (1S,8R)-lactams (yield greater than or equal to47%) could be easily separated. The ring opening of lactam enantiomers 1b-4b with 18% HCl afforded the corresponding beta-amino acid hydrochlorides 1c(.)HCl-4c(.)HCl (ee >95%). (C) 2004 Elsevier Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Forró, Enikő AU - Fülöp, Ferenc TI - Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of beta-lactams JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 15 PY - 2004 IS - 4 SP - 573 EP - 575 PG - 3 SN - 0957-4166 DO - 10.1016/j.tetasy.2003.12.034 UR - https://m2.mtmt.hu/api/publication/2326718 ID - 2326718 N1 - Cited By :48 Export Date: 3 June 2023 CODEN: TASYE Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, PO Box 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu Chemicals/CAS: 2 aminocyclopentanecarboxylic acid, 3814-46-8; diisopropyl ether, 108-20-3; triacylglycerol lipase, 9001-62-1 Funding details: Hungarian Scientific Research Fund, OTKA, 0115/2001, 181/2002, T 034901, TS 040888 Funding text 1: The authors acknowledge receipt of OTKA grants T 034901 and TS 040888, FKFP grant 0115/2001 and a Békésy Fellowship for EF (grant no. 181/2002). AB - 1, 4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.0(2.5)]nonan-4-one, (+/-)-1, and exo-3-azatricyclo[4.2.1.0(2.5)]non-7-en-4-one, (+/-)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1 equiv of H2O in diisopropyl ether at 70degreesC. The resolved beta-amino acids 1a and 2a (yield,46%) and beta-lactams 1b and 2b (yield greater than or equal to40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding beta-amino acid hydrochloride enantiomers (ee greater than or equal to98%). (C) 2004 Elsevier Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Fülöp, Ferenc AU - Forró, Enikő AU - Tóth, Gábor TI - A new strategy to produce beta-peptides: Use of alicyclic beta-lactams JF - ORGANIC LETTERS J2 - ORG LETT VL - 6 PY - 2004 IS - 23 SP - 4239 EP - 4241 PG - 3 SN - 1523-7060 DO - 10.1021/ol048356t UR - https://m2.mtmt.hu/api/publication/1013236 ID - 1013236 N1 - Megjegyzés-21956235 Z9: 11 WC: Chemistry, Organic AB - On p-methylbenzhydrylamine (MBHA) resin, by means of t-Boc chemistry, several tetrapeptides (H-Ala-ACXC-Ala-Gly-NH2) containing cyclic beta-amino acid units were prepared. These units were introduced into the growing peptide chain by using Boc-protected beta-lactams with KCN as catalyst in DMF. The method was applicable for both racemic and enantiomeric beta-lactams. LA - English DB - MTMT ER - TY - JOUR AU - Gyarmati, Zsuzsanna AU - Liljeblad, A AU - Argay, Gyula AU - Kálmán, A AU - Bernáth, Gábor AU - Kanerva, L TI - Chemoenzimatic preparation of enantiopure homoadamantyl beta-amino acid and beta-lactam derivatives JF - ADVANCED SYNTHESIS & CATALYSIS J2 - ADV SYNTH CATAL VL - 346 PY - 2004 IS - 5 SP - 566 EP - 572 PG - 7 SN - 1615-4150 DO - 10.1002/adsc.200303205 UR - https://m2.mtmt.hu/api/publication/118394 ID - 118394 N1 - Lab. of Synthetic Drug Chemistry, Department of Chemistry, University of Turku, Lemminkäisenkatu 2, 20520 Turku, Finland Inst. of Pharmaceutical Chemistry, Univ. Szeged Res. Grp. H., Hungarian Academy of Sciences, P.O. Box 121, 6701 Szeged, Hungary Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, P.O. Box 17, 1525 Budapest, Hungary Cited By :19 Export Date: 16 May 2023 CODEN: JPCHF Correspondence Address: Kanerva, L.T.; Lab. of Synthetic Drug Chemistry, Lemminkäisenkatu 2, 20520 Turku, Finland; email: lkanerva@utu.fi Chemicals/CAS: alcohol, 64-17-5; amide, 17655-31-1; butyric acid, 107-92-6, 156-54-7, 461-55-2; decane, 124-18-5; triacylglycerol lipase, 9001-62-1 LA - English DB - MTMT ER - TY - JOUR AU - Solymar, M AU - Kanerva, L T AU - Fülöp, Ferenc TI - Synthesis of the enantiomers and N-protected derivatives of 3-amino-3-(4-cyanophenyl)propanoic acid JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 15 PY - 2004 IS - 12 SP - 1893 EP - 1897 PG - 5 SN - 0957-4166 DO - 10.1016/j.tetasy.2004.05.012 UR - https://m2.mtmt.hu/api/publication/1013249 ID - 1013249 AB - Racemic ethyl 3-amino-3-(4-cyanophenyl)propanoate was synthesized and the enantiomers separated through enantioselective N-acylation by Candida antarctica lipase A (CAL-A) in neat butyl butanoate. The free amino acid enantiomers were transformed to the Boc and Fmoc-protected derivatives. (C) 2004 Elsevier Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Forró, Enikő AU - Fülöp, Ferenc TI - Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent JF - ORGANIC LETTERS J2 - ORG LETT VL - 5 PY - 2003 SP - 1209 EP - 1212 PG - 4 SN - 1523-7060 DO - 10.1021/ol034096o UR - https://m2.mtmt.hu/api/publication/1013530 ID - 1013530 N1 - Megjegyzés-21956242 Z9: 55 WC: Chemistry, Organic Megjegyzés-26797570 N1 CAPLUS AN 2003:213291(Journal) AB - A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic, beta-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase flipase B from Candida antarctica)-catalyzed reactions were performed with H2O (1 equiv) in dilsopropyl ether at 60 degreesC. The resolved products, obtained in good chemical yield (36-47%), could be easily separated. LA - English DB - MTMT ER - TY - JOUR AU - Gyarmati, Zsuzsanna AU - Liljeblad, A AU - Rintola, M AU - Bernáth, Gábor AU - Kanerva, L TI - Lipase-catalyzed kinetic resolution of 7-, 8- and 12-membered alicyclic beta-amino esters and N-hydroxymethyl-beta-lactam enantiomers JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 14 PY - 2003 IS - 23 SP - 3805 EP - 3814 PG - 10 SN - 0957-4166 DO - 10.1016/j.tetasy.2003.08.028 UR - https://m2.mtmt.hu/api/publication/118395 ID - 118395 N1 - Lab. of Synthetic Drug Chemistry, Department of Chemistry, University of Turku, Lemminkäisenkatu 2, FIN-20520 Turku, Finland Inst. of Pharmaceutical Chemistry, University of Szeged, Hungarian Academy of Sciences, PO Box 121, H-6701 Szeged, Hungary Cited By :25 Export Date: 16 May 2023 CODEN: TASYE Correspondence Address: Kanerva, L.T.; Lab. of Synthetic Drug Chemistry, Lemminkäisenkatu 2, FIN-20520 Turku, Finland; email: lkanerva@utu.fi Chemicals/CAS: acetone, 67-64-1 LA - English DB - MTMT ER - TY - JOUR AU - Park, S AU - Forró, Enikő AU - Grewal, H AU - Fülöp, Ferenc AU - Kazlauskas, R I TI - Molecular basis for the enantioselective ring opening of beta-lactams catalyzed by Candida antarctica lipase B JF - ADVANCED SYNTHESIS & CATALYSIS J2 - ADV SYNTH CATAL VL - 345 PY - 2003 SP - 986 EP - 995 PG - 10 SN - 1615-4150 DO - 10.1002/adsc.200303069 UR - https://m2.mtmt.hu/api/publication/1013524 ID - 1013524 N1 - Department of Chemistry, McGill University, 801 Sherbrooke St. W., Montréal, Que. H3A 3K6, Canada Inst. of Pharmaceutical Chemistry, University of Szeged, PO Box 121, H-6701 Szeged, Hungary Cited By :52 Export Date: 3 June 2023 CODEN: JPCHF Correspondence Address: Kazlauskas, R.J.; Department of Chemistry, 801 Sherbrooke St. W., Montréal, Que. H3A 3K6, Canada; email: romas.kazlauskas@mcgill.ca Chemicals/CAS: 2 octanol, 123-96-6; diisopropyl ether, 108-20-3; histidine, 645-35-2, 7006-35-1, 71-00-1; nitrogen, 7727-37-9; water, 7732-18-5 AB - Lipase B from Candida antarctica (CAL-B) catalyzes the slow, but highly enantioselective (E >200), ring-opening alcoholysis of two bicyclic and two 4-aryl-substituted beta-lactams. Surprisingly, the rate of the reaction varies with the nature of the alcohols and was fastest with either enantiomer of 2-octanol. A 0.5-g scale reaction with 2-octanol as the nucleophile in diisopropyl ether at 60degreesC yielded the unreacted beta-lactam in 39-46% yield (maximum yield is 50%) with greater than or equal to96% ee. The product beta-amino acid esters reacted further by polymerization (not isolated or characterized) or by hydrolysis due to small amounts of water in the reaction mixture yielding beta-amino acids (7-11% yield, greater than or equal to96% ee). The favored enantiomer of all four beta-lactams had similar 3-D orientation of substituents, as did most previously reported beta-lactams and beta-lactones in similar ring-opening reactions. Computer modeling of the ring opening of 4-phenylazetidin-2-one suggests that the reaction proceeds via an unusual substrate-assisted transition state, where the substrate alcohol bridges between the catalytic histidine and the nitrogen of the beta-lactam. Computer modeling also suggested that the molecular basis for the high enantioselectivity is a severe steric clash between Ile189 in CAL-B and the phenyl substituent on the slow-reacting enantiomer of the beta-lactam. LA - English DB - MTMT ER - TY - JOUR AU - Gedey, S AU - Liljeblad, A AU - Lázár, László AU - Fülöp, Ferenc AU - Kanerva, L T TI - Structural effects on chemo- and enantio-selectivity of Candida antarctica lipase B - Resolution of beta-amino esters JF - CANADIAN JOURNAL OF CHEMISTRY J2 - CAN J CHEM VL - 80 PY - 2002 IS - 6 SP - 565 EP - 570 PG - 6 SN - 0008-4042 DO - 10.1139/V02-015 UR - https://m2.mtmt.hu/api/publication/1013823 ID - 1013823 N1 - Cited By :22 Export Date: 16 May 2023 CODEN: CJCHA Correspondence Address: Kanerva, L.T.; Lab. of Synthetic Drug Chemistry, Lemminkäisenkatu 2, FIN-20520 Turku, Finland; email: lkanerva@utu.fi AB - The Candida antarctica lipase B-catalyzed reactions of five beta-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same beta-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated beta-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated la was performed to demonstrate the usefulness of the method. LA - English DB - MTMT ER - TY - JOUR AU - Solymar, M AU - Fülöp, Ferenc AU - Kanerva, L T TI - Candida antarctica lipase A - a powerful catalyst for the resolution of heteroaromatic beta-amino esters JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 13 PY - 2002 IS - 21 SP - 2383 EP - 2388 PG - 6 SN - 0957-4166 DO - 10.1016/S0957-4166(02)00637-7 UR - https://m2.mtmt.hu/api/publication/1013817 ID - 1013817 N1 - Megjegyzés-26797581 N1 CAPLUS AN 2002:862492(Journal) AB - Enantioselective acylations of 3-amino-3-beteroarylpropanoates (ArCH(NH2)CH2CO2Et; Ar = 2- or 3-thienyl or -furyl) were performed in the presence of Candida antarctica lipase A. As a result of the excellent chemo- and enantioselectivities (E > 100), gram-scale resolutions were carried out in ethyl butanoate. The hydrochloride salts of the unreacted R substrates and the butanamides of the reactive S enantiomers were thus prepared. (C) 2002 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Solymar, M AU - Liljeblad, A AU - Lázár, László AU - Fülöp, Ferenc AU - Kanerva, L T TI - Lipase-catalysed kinetic resolution in organic solvents: an approach to enantiopure alpha-methyl-beta-alanine esters JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 13 PY - 2002 IS - 17 SP - 1923 EP - 1928 PG - 6 SN - 0957-4166 DO - 10.1016/S0957-4166(02)00478-0 UR - https://m2.mtmt.hu/api/publication/1013820 ID - 1013820 N1 - Laboratory of Synthetic Drug Chemistry and Department of Chemistry, University of Turku, Lemminkäisenkatu 2, FIN-20520 Turku, Finland Institute of Pharmaceutical Chemistry, University of Szeged, PO Box 121, H-6701 Szeged, Hungary Cited By :26 Export Date: 16 May 2023 CODEN: TASYE Correspondence Address: Kanerva, L.T.; Lab. of Synthetic Drug Chemistry, Lemminkäisenkatu 2, FIN-20520 Turku, Finland Funding details: Hungarian Scientific Research Fund, OTKA Funding details: Kansainvälisen Liikkuvuuden ja Yhteistyön Keskus, CIMO Funding text 1: M.S. is grateful for a grant from the Centre for International Mobility (CIMO) in Finland. We thank the Hungarian Research Foundation (OTKA) for financial support. AB - The Candida antarctica lipase A (CAL-A) and B (CAL-B)-catalysed resolutions of alpha-methyl-beta-alanine ethyl ester 1 wit neat ethyl and butyl butanoates and with 2,12-trifluoroethyl butanoate in organic solvents Were Studied, as were the alcoholyses in neat butanol and with methanol (0.8 M) in diisopropyl ether. The two enzymes, which display opposite (S for CAL-A and R for CAL-B) and low enantioselectivities (E=7-10), allowed the preparation of the two enantiomers in a two-step resolution protocol. The R enantiomer (ee=97%) was first separated as its Boc-protected derivative front the CAL-A-catalysed resolution mixture of (R)-1 and the enantiomerically enriched N-butanoylated counterpart. The enantiopurification of the latter gave the S enantiomer (ec=96%)) in the following CAL-B-catalysed 'interesterification' in butyl butanoate. (C) 2002 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Forró, Enikő AU - Arva, J AU - Fülöp, Ferenc TI - Preparation of (1R,8S)- and (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one: potential starting compounds for the synthesis of anatoxin-a JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 12 PY - 2001 IS - 4 SP - 643 EP - 649 PG - 7 SN - 0957-4166 DO - 10.1016/S0957-4166(01)00100-8 UR - https://m2.mtmt.hu/api/publication/1013900 ID - 1013900 N1 - Cited By :44 Export Date: 25 May 2023 CODEN: TASYE Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu Funding details: Egészségügyi Tudományos Tanács, ETT, 32/2000 Funding details: Hungarian Scientific Research Fund, OTKA, 030452 Funding text 1: The authors thank OTKA (grant No. T 030452) and ETT (32/2000) for financial support. AB - 9-Azabicyclo[6.2.0]dec-4-en-10-one (+/-)-2, obtained from cyclooctadiene by addition of chlorosulfonyl isocyanate, was N-hydroxymethylated to (+/-)-3 and then resolved by lipase-catalysed asymmetric acylation of the primary OH group at the (S)-stereogenic centre. High enantioselectivity (E=94) was observed when lipase PS and vinyl butyrate were used in di-iso-propyl ether at -15 degreesC, resulting in the enantiomerically enriched ester 3a and alcohol 3b (e.e. greater than or equal to 92%). Treatment of 3a and 3b with NH4OH/MeOH afforded the corresponding beta -lactams (1R,8S)-2a and (1S,8R)-2b (e.e. greater than or equal to 93%), potential starting compounds in anatoxin-a synthesis. The ring opening of lactams (+/-)-2, (+/-)-7, 3a and 3b, followed by reduction, resulted in racemic 4-6 and 8 and enantiomeric 4a, 3b, 5a and 5b eight-membered cyclic beta -amino acid derivatives. (C) 2001 Published by Elsevier Science Ltd. LA - English DB - MTMT ER - TY - JOUR AU - Forró, Enikő AU - Fülöp, Ferenc TI - Synthesis of 4-aryl-substituted beta-lactam enantiomers by enzyme-catalyzed kinetic resolution JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 12 PY - 2001 IS - 16 SP - 2351 EP - 2358 PG - 8 SN - 0957-4166 DO - 10.1016/S0957-4166(01)00388-3 UR - https://m2.mtmt.hu/api/publication/1013890 ID - 1013890 N1 - Cited By :40 Export Date: 25 May 2023 CODEN: TASYE Correspondence Address: Fülöp, F.; Institute Pharmaceutical Chemistry, PO Box 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu AB - Enantiopure 4-phenyl- and 4-(p-tolyl)-2-azetidinones 3a, 3b, 4a and 4b (with e.e.s of greater than or equal to 96%) were prepared through lipase-catalyzed asymmetric butyrylation of the primary OH group of N-hydroxymethylated beta -lactams (+/-)-5 and (+/-)-6 at the (R)-stereogenic centre or by lipase-catalyzed asymmetric debutyrylation of O-butyryloxymethyl-2-azetidinones (+/-)-7 and (+/-)-8 at the (R)-stereogenic centre. The ring-opening of lactams 5a. 5b, 6b and 8a with HCl/EtOH afforded the corresponding P-amino ester enantiomers 9a, 9b, 10a and 10b with e.e.s or greater than or equal to 92%, (C) 2001 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Fülöp, Ferenc TI - The chemistry of 2-aminocycloalkanecarboxylic acids JF - CHEMICAL REVIEWS J2 - CHEM REV VL - 101 PY - 2001 IS - 7 SP - 2181 EP - 2204 PG - 24 SN - 0009-2665 DO - 10.1021/cr000456z UR - https://m2.mtmt.hu/api/publication/1013895 ID - 1013895 N1 - Cited By :361 Export Date: 3 June 2023 CODEN: CHREA Correspondence Address: Fülöp, F.; Institute of Pharmaceutical Chem., POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu Chemicals/CAS: Acids, Carbocyclic; Amino Acids, Cyclic; Analgesics, Opioid; Antifungal Agents; Antineoplastic Agents LA - English DB - MTMT ER - TY - JOUR AU - Gedey, S AU - Liljeblad, A AU - Lázár, László AU - Fülöp, Ferenc AU - Kanerva, L T TI - Preparation of highly enantiopure beta-amino esters by Candida antarctica lipase A JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 12 PY - 2001 IS - 1 SP - 105 EP - 110 PG - 6 SN - 0957-4166 DO - 10.1016/S0957-4166(01)00002-7 UR - https://m2.mtmt.hu/api/publication/1013902 ID - 1013902 N1 - Department of Chemistry and Laboratory of Synthetic Drug Chemistry, University of Turku, Lemminkäisenkatu 2, FIN-20520 Turku, Finland Institute of Pharmaceutical Chemistry, University of Szeged, PO Box 121, H-6701 Szeged, Hungary Cited By :76 Export Date: 3 June 2023 CODEN: TASYE Correspondence Address: Kanerva, L.T.; Department of Chemistry, Lemminkäisenkatu 2, FIN-20520 Turku, Finland; email: lkanerva@utu.fi Funding details: FKFP 0535/1999 Funding details: Kansainvälisen Liikkuvuuden ja Yhteistyön Keskus, CIMO Funding text 1: S.G. is grateful for a grant from the Centre for International Mobility (CIMO) in Finland. Support from the Technology Development Centre (TEKES) in Finland and from MKM (Grant No. FKFP 0535/1999) in Hungary is also gratefully acknowledged. AB - The enantioselectivities for the reactions of aliphatic beta -substituted beta -amino esters [RCH(NH2)CH2CO2Et with R = Me, Et, n-Pr, i-Pr, CHEt2, cyclohexyl and Ph] with butyl butanoate in neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied in the presence of Candida antarctica lipase A. Enantioselectivities ranging from good (E=70-100) to excellent (E>100) were commonly observed, allowing gram-scale resolution of the substrates. (C) 2001 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Kaman, J AU - van Der, Eycken J AU - Péter, Antal AU - Fülöp, Ferenc TI - Enzymatic resolution of bicyclic 1,3-amino alcohols in organic media JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 12 PY - 2001 IS - 4 SP - 625 EP - 631 PG - 7 SN - 0957-4166 DO - 10.1016/S0957-4166(01)00093-3 UR - https://m2.mtmt.hu/api/publication/1013899 ID - 1013899 N1 - Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S.4), B-9000 Gent, Belgium Institute of Pharmaceutical Chemistry, University of Szeged, POB 121, H-6701 Szeged, Hungary Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6701 Szeged, Hungary Cited By :14 Export Date: 25 May 2023 CODEN: TASYE Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu Funding details: 1.5.930.95 Funding details: BIL 98/28 Funding details: Vlaamse Overheid Funding details: Hungarian Scientific Research Fund, OTKA Funding text 1: This work was supported by a COPERNICUS project (Contract No. ERBCIPA-CT94-0121). F.F. thanks OTKA for their financial support. J.VdE. thanks the Fund for Scientific Research, Flanders (F.W.O., Belgium) for a Research Grant (No. 1.5.930.95) and the ‘Ministerie van de Vlaamse Gemeeschap’ for financial support (BIL 98/28). We are indebted to Amano Enzyme Europe and Novo Nordisk for the generous gift of the lipases. AB - N-Protected racemic di-exo- and di-endo-3-aminobicyclo[2.2.1]heptane-2-methanols and di-exo- and di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-methanols were resolved through lipase-catalysed O-acylation, using vinyl butyrate in organic solvents. Of the lipases screened most showed a preference for the (2S)-enantiomer. (C) 2001 Published by Elsevier Science Ltd. LA - English DB - MTMT ER - TY - JOUR AU - Fülöp, Ferenc AU - Palkó, Márta AU - Kaman, J AU - Lázár, László AU - Sillanpaa, R TI - Synthesis of all four enantiomers of 1-aminoindane-2-carboxylic acid, a new cispentacin benzologue JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 11 PY - 2000 IS - 20 SP - 4179 EP - 4187 PG - 9 SN - 0957-4166 DO - 10.1016/S0957-4166(00)00375-X UR - https://m2.mtmt.hu/api/publication/1014471 ID - 1014471 N1 - Megjegyzés-22907514 Z9: 22 DI: 10.1016/S0957-4166(00)00375-X AB - Racemic cis- and trans-1-aminoindane-2-carboxylic acids (3 and 5) were prepared from indene by chlorosulphonyl isocyanate addition followed by ring opening and isomerisation. The intermediate racemic hydroxymethylated beta -lactam 6 was resolved through the lipase-catalysed asymmetric acylation of the primary hydroxy group at the (R)-stereogenic centre. High enantioselectivities (E>200) were observed when the enzymatic reactions were performed with lipase AK or lipase PS as catalyst and vinyl acetate or vinyl butyrate as acyl donor. The hydrolysis and isomerisation resulted in all four enantiomers (9, 11, 13 and 14) of 1-aminoindane-2-carboxylic acid, a new benzologue of cispentacin. (C) 2000 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - CHAP AU - Fülöp, Ferenc ED - Atta-Ur, Rahman TI - The chemistry of 2-aminocyclopentanecarboxylic acid T2 - Studies in Natural Products Chemistry: Bioactive Natural Products (Part C) PB - Elsevier CY - New York, New York SN - 0444505881 T3 - Studies in Natural Products Chemistry, ISSN 1572-5995 ; 22. PY - 2000 SP - 273 EP - 306 PG - 34 DO - 10.1016/S1572-5995(00)80028-9 UR - https://m2.mtmt.hu/api/publication/1014519 ID - 1014519 LA - English DB - MTMT ER - TY - JOUR AU - Kaman, J AU - Forró, Enikő AU - Fülöp, Ferenc TI - Enzymatic resolution of alicyclic beta-lactams JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 11 PY - 2000 IS - 7 SP - 1593 EP - 1600 PG - 8 SN - 0957-4166 DO - 10.1016/S0957-4166(00)00070-7 UR - https://m2.mtmt.hu/api/publication/1014473 ID - 1014473 N1 - Cited By :41 Export Date: 30 May 2023 CODEN: TASYE Correspondence Address: Fulop, F.; Institute Pharmaceutical Chemistry, PO Box 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu Funding details: FKFP 0535/1999 Funding details: Hungarian Scientific Research Fund, OTKA, 030452 Funding text 1: The authors' thanks are due to OTKA (grant No. T 030452) and MKM (grant No. FKFP 0535/1999) for financial support. AB - Racemates of N-hydroxymethylated beta-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E > 200) was observed when the enzymatic reactions were performed in acetone with lipase PS as catalyst and vinyl butyrate as acyl donor. The hydrolysis of the enantiomeric azetidinones 4a-6a and 4b-6b resulted in the enantiomerically pure alicyclic beta-amino acids 4c-6c and 4d-6d. When the less reactive enantiomers 4b-6b were treated with NH4OH/MeOH, enantiomerically pure beta-lactams 4e-6e were formed. (C) 2000 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Szakonyi, Zsolt AU - Martinek, Tamás AU - Hetényi, Anasztázia AU - Fülöp, Ferenc TI - Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 11 PY - 2000 IS - 22 SP - 4571 EP - 4579 PG - 9 SN - 0957-4166 DO - 10.1016/S0957-4166(00)00435-3 UR - https://m2.mtmt.hu/api/publication/1014481 ID - 1014481 N1 - Cited By :50 Export Date: 8 September 2023 CODEN: TASYE Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu AB - Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-alpha -pinene I resulted in enantiomerically pure beta -lactams 2, which were converted to enantiomeric beta -amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The resulting 1,3-difunctional compounds 3, 4 and 6 were transformed to fused saturated 1,3-heterocycles such as tetrahydro-1,3- oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin- 4-one 13 enantiomers. (C) 2000 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Gedey, S AU - Liljeblad, A AU - Fülöp, Ferenc AU - Kanerva, L T TI - Sequential resolution of ethyl 3-aminobutyrate with carboxylic acid esters by Candida antarctica lipase B JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 10 PY - 1999 SP - 2573 EP - 2581 PG - 9 SN - 0957-4166 UR - https://m2.mtmt.hu/api/publication/1014573 ID - 1014573 AB - The reactions of ethyl 3-aminobutyrate 1 with carboxylic acid esters, catalyzed by lipases from Candida antarctica, Pseudomonas cepacia and Pseudomonas fluorescens, have been studied. The reactions take place on the amino and ester functions of the substrate provided that the alkyl group of the achiral ester differs from ethyl. This property has been exploited for the Candida antarctica lipase B-catalyzed resolution of 1 in butyl butyrate, leading to the unreacted enantiomer (S)-1 and butyl 3-aminobutyrate, and to the butanamide of butyl (R)-3-aminobutyrate, (C) 1999 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Lázár, László AU - Martinek, Tamás AU - Bernáth, Gábor AU - Fülöp, Ferenc TI - A simple synthesis of beta-alkyl-substituted beta-amino acids JF - SYNTHETIC COMMUNICATIONS J2 - SYNTHETIC COMMUN VL - 28 PY - 1998 IS - 2 SP - 219 EP - 224 PG - 6 SN - 0039-7911 DO - 10.1080/00397919808005714 UR - https://m2.mtmt.hu/api/publication/27976 ID - 27976 N1 - Cited By :33 Export Date: 8 September 2023 CODEN: SYNCA Correspondence Address: Fulop, F.; Institute Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary AB - By the condensation of branched-chain aliphatic or alicyclic aldehydes with malonic acid in the presence of ammonium acetate, beta-alkyl-substituted beta-amino acids were prepared. LA - English DB - MTMT ER - TY - JOUR AU - Péter, Mária AU - van Der, Eycken J AU - Bernáth, Gábor AU - Fülöp, Ferenc TI - Enzymatic resolution of alicyclic 1,3-amino alcohols in organic media JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 9 PY - 1998 IS - 13 SP - 2339 EP - 2347 PG - 9 SN - 0957-4166 DO - 10.1016/S0957-4166(98)00236-5 UR - https://m2.mtmt.hu/api/publication/27972 ID - 27972 N1 - Department of Organic Chemistry, University of Gent, Krijgslaan 281 (S.4), B-9000 Gent, Belgium Inst. of Pharmaceutical Chemistry, Albert Szent-Györgyi Med. Univ., POB 121, H-6701 Szeged, Hungary Cited By :23 Export Date: 25 May 2023 CODEN: TASYE Correspondence Address: Van der Eycken, J.; Department of Organic Chemistry, Krijgslaan 281 (S.4), B-9000 Gent, Belgium; email: Johan.Vandereycken@rug.ac.be Funding details: 1.5.930.95 Funding details: Vlaamse Overheid Funding details: Hungarian Scientific Research Fund, OTKA Funding text 1: This work was supported by a COPERNICUS project (Contract No. ERBCIPA-CT94-0121). GB and FF thank OTKA for their financial support. JVdE thanks the Fund for Scientific Research, Flanders (F.W.O., Belgium) for a `Krediet aan Navorsers' (No. 1.5.930.95) and the `Ministerie voor Wetenschapsbeleid' for financial support. We are indebted to Amano Enzyme Europe and Novo Nordisk for the generous gift of the lipases and proteases. PM thanks the Soros Foundation for financial support. AB - Racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans-2-amino-4-cyclohexene-1-methanol were resolved via lipase-catalysed O-acylation of their Z derivatives, using vinyl butyrate in different ether solvents. In accordance with the empirical rule, most of the screened lipases preferred the 1S enantiomer. (C) 1998 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Csomós, Péter AU - Kanerva, LT AU - Bernáth, Gábor AU - Fülöp, Ferenc TI - Biocatalysis for the preparation of optically active beta- lactam precursors of amino acids JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 7 PY - 1996 IS - 6 SP - 1789 EP - 1796 PG - 8 SN - 0957-4166 DO - 10.1016/0957-4166(96)00214-5 UR - https://m2.mtmt.hu/api/publication/27988 ID - 27988 AB - Enantioselective acylation of N-hydroxymethylated beta-lactams in the presence of Pseudomonas sp. lipase afforded optically active precursors for the preparation of (1R,2S)- and (1S,2R)-2-aminocyclopentane- and (1R,2S,3R,4S)- and (1S,2R,3S,4R)-3-aminobicyclo[2.2.1]heptanecarboxylic acids. Due to the high enantioselectivity (E = 90 and 62) and in order to minimize the enzymatic hydrolysis of the acylated products back to the starting alcohol, the reactions were performed in acetone. Copyright (C) 1996 Elsevier Science Ltd LA - English DB - MTMT ER - TY - JOUR AU - Kanerva, LT AU - Csomós, Péter AU - Sundholm, O AU - Bernáth, Gábor AU - Fülöp, Ferenc TI - Approach to highly enantiopure beta-amino acid esters by using lipase catalysis in organic media JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 7 PY - 1996 IS - 6 SP - 1705 EP - 1716 PG - 12 SN - 0957-4166 DO - 10.1016/0957-4166(96)00204-2 UR - https://m2.mtmt.hu/api/publication/27987 ID - 27987 AB - Ethyl esters often alicyclic beta-aminocarboxylic acids were resolved by lipase catalysis in organic solvents. The resolution was based on acylation of the amino group at the R-stereogenic centre with various 2,2,2-trifluoroethyl esters. An increase in the hydrophobic nature of the acyl donor enhanced the enantioselectivity and reactivity in the case of lipase SP 526 from Candida antarctica, while the opposite effect was observed with lipase PS from Pseudomonas cepacia. An unexceptional enantioselectivity enhancement was observed when 2,2,2-trifluoroethyl chloroacetate was used in the case oflipase PS catalysis. Copyright (C) 1996 Elsevier Science Ltd LA - English DB - MTMT ER -