FEASIBILITY OF USING DIFFERENT IONIC LIQUIDS FOR THE ENZYMATIC SYNTHESIS OF AMOXICILLIN

FEASIBILITY OF USING DIFFERENT IONIC LIQUIDS FOR THE ENZYMATIC SYNTHESIS OF AMOXICILLIN

PEREIRA, S. C.; KOPP, W.; DURO, M. A. I.; SILVA, S. M.; BUSSAMARA, R.; MARIN, G.; DUPONT, J.; GIORDANO, R. L. C.; GIORDANO, R. C.

Artigo:

Industrially, amoxicillin has been produced by chemical processes. But, the enzymatic synthesis catalyzed by penicillin G acylase (PGA, E.C.3.5.1.11) is more attractive from the environmental point of view. However, an obstacle for the industrial application of the enzymatic route is the limited product yield due to undesirable hydrolytic reactions. This drawback can be minimized by reducing water activity in the reaction medium. Ionic liquids (ILs) have emerged as an alternative to conventional organic media. This study assessed the feasibility of use of different ILs, protic (PILs) and aprotic (AILs), in the enzymatic synthesis of amoxicillin, by testing the stability of reaction substrates (6-aminopenicillanic acid and p-hydroxyphenylglycine methyl ester) in these solvents. These compounds were completely stable in AILs. Besides, PGA was active in AILs. In contrast, none of the evaluated PILs was inert for these substrates making unfeasible the use for this enzymatic process.

Industrially, amoxicillin has been produced by chemical processes. But, the enzymatic synthesis catalyzed by penicillin G acylase (PGA, E.C.3.5.1.11) is more attractive from the environmental point of view. However, an obstacle for the industrial application of the enzymatic route is the limited product yield due to undesirable hydrolytic reactions. This drawback can be minimized by reducing water activity in the reaction medium. Ionic liquids (ILs) have emerged as an alternative to conventional organic media. This study assessed the feasibility of use of different ILs, protic (PILs) and aprotic (AILs), in the enzymatic synthesis of amoxicillin, by testing the stability of reaction substrates (6-aminopenicillanic acid and p-hydroxyphenylglycine methyl ester) in these solvents. These compounds were completely stable in AILs. Besides, PGA was active in AILs. In contrast, none of the evaluated PILs was inert for these substrates making unfeasible the use for this enzymatic process.

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DOI: 10.5151/chemeng-cobeq2014-1248-20264-138554

Referências bibliográficas

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• [9] 6. ACKNOWLEDGEMENTS The authors would like to thank Brazilian research-funding agencies (CAPES, CNPq and FAPESP) and the group of the Prof. Guisán (Department of Enzymatic Biocatalysis, Institute of Catalysis, CSIC, Madrid, Spain) for the biocatalyst.

Como citar:

PEREIRA, S. C.; KOPP, W.; DURO, M. A. I.; SILVA, S. M.; BUSSAMARA, R.; MARIN, G.; DUPONT, J.; GIORDANO, R. L. C.; GIORDANO, R. C.; "FEASIBILITY OF USING DIFFERENT IONIC LIQUIDS FOR THE ENZYMATIC SYNTHESIS OF AMOXICILLIN", p-1793-1800. In: Anais do XX Congresso Brasileiro de Engenharia Química - COBEQ 2014 [= Blucher Chemical Engineering Proceedings, v.1, n.2]. São Paulo: Blucher, 2015.
ISSN 23591757, DOI 10.5151/chemeng-cobeq2014-1248-20264-138554