SÍNTESE ENZIMÁTICA DE BUTIRATO DE GERANILA POR ESTERIFICAÇÃO CATALISADA POR LIPASE IMOBILIZADA EM RESINA HIDROFÓBICA

Adriano Aguiar Mendes

Resumo


Neste estudo, um biocatalisador foi preparado por imobilização de lipase de Thermomyces lanuginosus (LTL) em partículas hidrofóbicas de poli-estireno-divinilbenzeno e empregado na síntese de butirato de geranila por esterificação direta de geraniol e ácido butírico em meio de hexano. O biocatalisador foi preparado com carregamento inicial de proteína de 40  mg g-1 de suporte e alta concentração de proteína imobilizada, da ordem de 39  mg g-1 de suporte, foi observada. O efeito de relevantes na síntese do éster foi determinado. As condições reacionais que maximizaram a síntese do éster foram concentração de biocatalisador de 10% m v-1, temperatura de 40°C e concentração de 1 mol L-1 de cada reagente que apresentou máxima conversão da ordem de 85% após 3 h de reação. Nestas condições ótimas, foi realizada a estabilidade operacional do biocatalisador após cinco sucessivos ciclos de reação e ele manteve 65% de sua atividade inicial. Estes resultados mostram que o suporte testado é bastante promissor na preparação de biocatalisadores ativos na síntese de ésteres de aroma por reação de esterificação.

Palavras-chave


butirato de geranila; esterificação; imobilização; lipase; reuso

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Referências


ADLERCREUTZ, P. Immobilisation and application of lipases in organic media. Chemical Society Reviews, v. 42, p. 6406-6436, 2013.

AKACHA N.B.; GARGOURI M. Microbial and enzymatic technologies used for the production of natural aroma compounds: Synthesis, recovery modeling, and bioprocesses. Food and Bioproducts Processing, v. 94, p. 675-706, 2015.

ALVES, M.D.; CREN, E.C.; MENDES, A.A. Kinetic, thermodynamic, optimization and reusability studies for the enzymatic synthesis of a saturated wax ester. Journal of Molecular Catalysis B: Enzymatic, v. 133, p. S377-S387, 2017.

ALVES, M.D.; ARACRI, F.M.; CREN, E.C.; MENDES, A.A. Isotherm, kinetic, mechanism and thermodynamic studies of adsorption of a microbial lipase on a mesoporous and hydrophobic resin. Chemical Engineering Journal, v. 311, p. 1-12, 2017.

BASSI J.J.; TODERO L.M.; LAGE F.A.P.; KHEDY G.I.; DELL DUCAS J.; CUSTÓDIO A.P.; PINTO M.A.; MENDES A.A. Interfacial activation of lipases on hydrophobic support and application in the synthesis of a lubricant ester. International Journal of Biological Macromolecules, v. 92, p. 900-909, 2016.

BRADFORD, M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry, v. 72, p. 248-254, 1976.

CABRERA Z.; FERNANDEZ-LORENTE G.; FERNANDEZ-LAFUENTE R.; PALOMO J.M.; GUISAN, J.M. Novozym 435 displays very different selectivity compared to lipase from Candida antarctica B adsorbed on other hydrophobic supports. Journal of Molecular Catalysis B: Enzymatic, v. 56, p. 171-176, 2009.

CORRADINI M.C.C.; GOMES R.A.B.; LUIZ J.H.H.; MENDES A.A. Optimization of enzymatic synthesis of n-propyl acetate (fruit flavor ester) – Effect of the support on the properties of biocatalysts. Chemical Engineering Communications, v. 203, p. 1432-1442, 2016.

CORRADINI M.C.C.; COSTA B.M.; BRESSANI A.P.P.; GARCIA K.C.A.; PEREIRA E.B.; MENDES A.A. Improvement of the enzymatic synthesis of ethyl valerate by esterification reaction in a solvent system. Preparative Biochemistry and Biotechnology, v. 47, p. 100-109, 2017.

DAMNJANOVIC J.J.; ZUZA M.G.; SAVANOVIC J.K.; BEZBRADICA D.I.; MIJIN D.Z.; BOSKOVIC-VRAGOLOVIC N.; KNEZEVIC-JUGOVIC Z.D. Covalently immobilized lipase catalyzing high-yielding optimized geranyl butyrate synthesis in a batch and fluidized bed reactor. Journal of Molecular Catalysis B: Enzymatic, v. 75, p. 50-59, 2012.

DE BARROS, D.P.C.; AZEVEDO, A.M.; CABRAL, J.M.S.; FONSECA, L.P. Optimization of flavor esters synthesis by Fusarium solani pisi cutinase. Journal of Food Biochemistry, v. 36, p. 275-284, 2012.

DHAKE K.P.; THAKARE D.D.; BHANAGE, B.M. Lipase: A potential biocatalyst for the synthesis of valuable flavour and fragrance ester compounds. Flavour and Fragrance Journal, v. 28, p. 71-83, 2013.

FLAVOR AND EXTRACT MANUFACTURERS ASSOCIATION OF THE UNITED STATES (FEMA), 2019. Disponível em: https://www.femaflavor.org/flavor-library/geranyl-butyrate. Acessado em 18 de maio de 2019.

FERNANDEZ-LAFUENTE, R. Lipase from Thermomyces lanuginosus: Uses and prospects as an industrial biocatalyst. Journal of Molecular Catalysis B: Enzymatic, v. 62, p. 197-212, 2010.

FRIEDLICH, J.L.R.; PEÑA, F.P.; GARCIA-GALAN, C.; FERNANDEZ-LAFUENTE, R.; AYUB, M.A.Z.; RODRIGUES, R.C. Effect of immobilization protocol on optimal conditions of ethyl butyrate synthesis catalyzed by lipase B from Candida antarctica. Journal of Chemical Technology and Biotechnology, v. 88, p. 1089-1095, 2013.

GUO, Z.; XU, X. Lipase-catalyzed glycerolysis of fats and oils in ionic liquids: a further study on the reaction system. Green Chemistry, v. 8, p 54-62, 2006.

IWAI, I.; OKUMURA, S.; TSUJISAKA, Y. Synthesis of terpene alcohol esters by lipase. Agricultural and Biological Chemistry, v. 44, p. 2731-2732, 1980.

JIN Z.; NTWALI J.; LIN Y.; KUI H.; ZHENG S.; HAN S. Geranyl butyrate production by Candida antarctica lipase B-displaying Pichia pastoris. In: Zhang T.C. and Nakajima M. (eds.). Advances in Applied Biotechnology. Springer-Verlag, Berlin, Cap. 39, 2015.

LORENZONI A.S.G.; GRAEBIN N.G.; MARTINS A.B.; FERNANDEZ-LAFUENTE R.; AYUB M.A.Z.; RODRIGUES R.C. Optimization of pineapple flavour synthesis by esterification catalysed by immobilized lipase from Rhizomucor miehei. Fravour and Fragrance Journal, v. 27, p. 196–200, 2012.

POORNIMA, K.; PREETHA, R. Biosynthesis of food flavours and fragrances - A review. Asian Journal of Chemistry, v. 29, p. 2345-2352.

OZYILMAZ, G.; GEZER, E. Production of aroma esters by immobilized Candida rugosa and porcine pancreatic lipase into calcium alginate gel. Journal of Molecular Catalysis B: Enzymatic, v. 64, p. 140-145, 2010.

SÁ, A.G.A.; DE MENEZES, A.C., DE ARAÚJO, P.H.H.; DE OLIVEIRA, D. A review on enzymatic synthesis of aromatic esters used as flavor ingredients for food, cosmetics and pharmaceuticals industries. Trends in Food Science & Technology, v. 69, p. 95-105, 2017.

SBARDELOTTO C.R. Síntese de butanoato de geranila (aroma de cereja) via esterificação enzimática em sistema livre de solvente orgânico. Dissertação de Mestrado, Universidade Regional Integrada do Alto Uruguai e das Missões, 2015.

SECUNDO, F.; MIEHÉ-BRENDLÉ, J.; CHERALU, C.; FERRANDI, E.E.; DUMITRIU, E. Adsorption and activities of lipases on synthetic beidellite clays with variable composition. Microporous and Mesoporous Materials, v. 109, p. 350-361, 2008.

TODERO, L.M.; BASSI, J.J.; LAGE, F.A.P.; CORRADINI, M.C.C.; BARBOZA, J.C.S.; HIRATA, D.B.; MENDES, A.A. Enzymatic synthesis of isoamyl butyrate catalyzed by immobilized lipase on poly-methacrylate particles: optimization, reusability and mass transfer studies. Bioprocess and Biosystems Engineering, v. 38, p. 1601-1613, 2015.

TORRES, S.; BAIGORI, M.D.; SWATHY, S.L.; PANDEY, A.; CASTRO, G.R. Enzymatic synthesis of banana flavour (isoamyl acetate) by Bacillus licheniformis S-86 esterase. Food Research International, v. 42, p. 454-460, 2009.

YADAV, G.D.; DHOOT, S.B. Immobilized lipase-catalysed synthesis of cinnamyl laurate in non-aqueous media. Journal of Molecular Catalysis B: Enzymatic, v. 57, p. 34-39, 2009.




DOI: https://doi.org/10.18540/jcecvl5iss4pp0386-0391

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