Síntese enantiosseletiva de amidas e ésteres catalisada por lipases
作者： Neide Queiroz
DOI:
关键词:
摘要: QUEIROZ, Neide. Sintese Enantiosseletiva de Amidas e Esteres Catalisada por Lipases. Florianopolis, 2002. 152f. Tese (Doutorado em Quimica Orgânica) – Programa Pos-graduacao Quimica, UFSC. Orientadora: Maria da Graca Nascimento Defesa: 20/12/2002 In order to synthesize enantiopure compounds , the chemists depend on disponibility of chiral materials. this work, it was investigated production acids, amines and amides optically pure, via enzymatic resolution racemic acids amines. Hydroxy(phenyl) acetic acid compound more extensively due presence hydroxy carboxyl group. To obtain pure enantiomers, esterification carboxylic acylation hydroxyl group catalyzed by lipases accomplished. The reactions with n-pentanol yielded ester in 10% conversion using Pseudomonas sp lipase immobilyzed agar gel (PSL/agar) after 336 h, 26% Candida antarctica (CAL) 840 h reaction at 25 °C. were realized derivatization corresponding methyl ester. esters acylated vinyl acetate, free PSL or immobilized poly (ethylene oxide) (PEO) gel, various organic solvents . Excellent results obtained PEO isopropyl ether as solvent For system, enantiomeric excess (ee) for substrate product >99% near 50%. ratio also excellent, being 1057. system PSL/free an E value 230 obtained. both cases, enantiopreference S isomer. 2and 3-Alkylalkanoic 2-bromoalkanoic submitted No recognition observed 2-alkylalkanoic However, 2-bromo alkanoic discriminated CAL but still showed a low enantioselectivity values 1.2-10. biocatalytic aminolysis (R,S)–hydroxy(phenyl)acetate (R,S)-2-chrorophenoxy) propanoate 1-butylamine 1octylamine, hexane °C, studied ( E= 1.2-2.7) Risomer. 1-ethylpenthylamine, 1methylhexylamine, 1-phenylethylamine, 1,2-dimethylpropylamine 2-ethylhexylmaine PSL, highly dependent amine structure. 24-79 biocatalyst, forming only Biological activity some (acids, esteres ) pures amides) evaluated pharmacological tests. suggested that 2-bromoalkylalkanoic hydroxy(phenyl)acetate its derivatives had antinociceptive these might be used new substances analgesic potencial.
参考文章(136)
Takeshi Sugai, Hideaki Kakeya, Hiromichi Ohta, Mitsuo Morooka, Shigeru Ohba, None, A synthesis of (−)-deoxypodocarpic acid methyl ester via an enzymatic enantioselective hydrolysis of the key intermidiate enol ester Tetrahedron. ,vol. 45, pp. 6135- 6144 ,(1989) , 10.1016/S0040-4020(01)85126-7
Yoshitaka Yasufuku, Shin-ichi Ueji, Effect of temperature on lipase-catalyzed esterification in organic solvent Biotechnology Letters. ,vol. 17, pp. 1311- 1316 ,(1995) , 10.1007/BF00189216
Neeru Munjal, SK Sawhney, None, Stability and properties of mushroom tyrosinase entrapped in alginate, polyacrylamide and gelatin gels Enzyme and Microbial Technology. ,vol. 30, pp. 613- 619 ,(2002) , 10.1016/S0141-0229(02)00019-4
P Lozano, AB Pérez-Marın, Teresa De Diego, D Gomez, Delphine Paolucci-Jeanjean, MP Belleville, GM Rios, JL Iborra, Active membranes coated with immobilized Candida antarctica lipase B: preparation and application for continuous butyl butyrate synthesis in organic media Journal of Membrane Science. ,vol. 201, pp. 55- 64 ,(2002) , 10.1016/S0376-7388(01)00703-7
Alexander E. Ivanov, Manfred P. Schneider, Methods for the immobilization of lipases and their use for ester synthesis Journal of Molecular Catalysis B-enzymatic. ,vol. 3, pp. 303- 309 ,(1997) , 10.1016/S1381-1177(97)00012-X
Kaoru Nakamura, Masamichi Kinoshita, Atsuyoshi Ohno, Effect of solvent on lipase-catalyzed transesterification in organic media Tetrahedron. ,vol. 50, pp. 4681- 4690 ,(1994) , 10.1016/S0040-4020(01)85007-9
Arie L. Gutman, Elazar Meyer, Evgeny Kalerin, Felix Polyak, Jeffrey Sterling, Enzymatic resolution of racemic amines in a continuous reactor in organic solvents Biotechnology and Bioengineering. ,vol. 40, pp. 760- 767 ,(1992) , 10.1002/BIT.260400703
Arto Liljeblad, Jutta Lindborg, Anu Kanerva, Johanna Katajisto, Liisa T. Kanerva, Enantioselective lipase-catalyzed reactions of methyl pipecolinate: transesterification and N-acylation Tetrahedron Letters. ,vol. 43, pp. 2471- 2474 ,(2002) , 10.1016/S0040-4039(02)00288-5
Pedro C de Oliveira, Gizelda M Alves, Heizir F de Castro, Immobilisation studies and catalytic properties of microbial lipase onto styrene–divinylbenzene copolymer Biochemical Engineering Journal. ,vol. 5, pp. 63- 71 ,(2000) , 10.1016/S1369-703X(99)00061-3
Hiroshi Kitaguchi, Paul A. Fitzpatrick, Joel E. Huber, Alexander M. Klibanov, Enzymic resolution of racemic amines: crucial role of the solvent Journal of the American Chemical Society. ,vol. 111, pp. 3094- 3095 ,(1989) , 10.1021/JA00190A070