Lipase-catalyzed synthesis of substituted phenylacetamides: Hammett analysis and computational study of the enzymatic aminolysis

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A series of hydroxy-, methoxy-, and nitrophenylacetamides was synthesized by enzyme catalysis. The 28 new products were obtained through a lipase-catalyzed two-step reaction in very good to excellent yield. In the case of nitro derivatives, a one-pot, two-step methodology allowed the desired product...

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Autor principal: García Liñares, G.
Otros Autores: Arroyo Mañez, P., Baldessari, A.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Wiley-VCH Verlag 2014
Acceso en línea:Registro en Scopus
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100 1 |a García Liñares, G. 
245 1 0 |a Lipase-catalyzed synthesis of substituted phenylacetamides: Hammett analysis and computational study of the enzymatic aminolysis 
260 |b Wiley-VCH Verlag  |c 2014 
270 1 0 |m Baldessari, A.; Laboratorio de Biocatálisis, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, piso 3, Argentina 
506 |2 openaire  |e Política editorial 
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520 3 |a A series of hydroxy-, methoxy-, and nitrophenylacetamides was synthesized by enzyme catalysis. The 28 new products were obtained through a lipase-catalyzed two-step reaction in very good to excellent yield. In the case of nitro derivatives, a one-pot, two-step methodology allowed the desired products to be obtained in high yields. The influence of various reaction parameters in the lipase-catalyzed reactions, such as enzyme source, nucleophile (alcohol or amine)/substrate ratio, enzyme/substrate ratio, solvent and temperature were studied. It was observed that nitro-substituted phenylacetates were more reactive in the aminolysis reaction than phenylacetates substituted with a hydroxyl group. To study this substituent effect, a Hammett analysis and the determination of the ρ parameter were carried out. Moreover, a computational study was applied to the most representative systems, performing an exploration of the potential energy surface for the catalyzed and noncatalyzed aminolysis reaction for nitro- and hydroxyphenylacetates. Both analysis showed that the presence of a strongly electron-attracting group favors the activity of the enzyme, in complete agreement with the experimental results of the enzymatic catalysis. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA.  |l eng 
593 |a Laboratorio de Biocatálisis, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, piso 3, Buenos Aires, C1428EGA, Argentina 
593 |a Laboratorio de Modelado Molecular, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, piso 3, Buenos Aires, C1428EGA, Argentina 
690 1 0 |a AMIDES 
690 1 0 |a ENZYME CATALYSIS 
690 1 0 |a ESTERS 
690 1 0 |a MOLECULAR MODELING 
690 1 0 |a REACTION MECHANISMS 
700 1 |a Arroyo Mañez, P. 
700 1 |a Baldessari, A. 
773 0 |d Wiley-VCH Verlag, 2014  |g v. 2014  |h pp. 6439-6450  |k n. 29  |p Eur. J. Org. Chem.  |x 1434193X  |w (AR-BaUEN)CENRE-1605  |t European Journal of Organic Chemistry 
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