Abstract
Phenylacetic acid can be produced from 2-phenylethanol by selective oxidation. This process can be performed using Gluconobacter oxydans immobilized in LentiKats®, polyvinyl alcohol particles with lenticular shape. The biotransformation took place at non-growth conditions in an airlift bioreactor. The goal of this work was to examine the impact of the particles on the hydrodynamics and volumetric mass transfer coefficient for oxygen in the airlift reactor and to describe the activity of the immobilized biomass in such systems. For this purpose, the influence of aeration and 2-phenylethanol concentration on the activity of biomass was examined. Also, the effects of long-term storage of immobilized biomass, long duration of fermentation and repeated use of biomass on the rate of phenylacetic acid production were tested. The results were compared with the phenylacetic acid production by free cells of Gluconobacter oxydans. The results show that aeration of the airlift reactor has only a minor effect on the phenylacetic acid production for immobilized biomass but a significant one for free cells; however, the impact of 2-phenylethanol concentration on the production was notable for both forms of biocatalyst depending on the biomass concentration. Production ability of free cells was ten times higher than that of immobilized cells, but the production time was only a quarter of that of immobilized cells.
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References
Anes J, Fernandes P (2014) Towards the continuous production of fructose syrups from inulin using inulinase entrapped in PVA-based particles. Biocatal Agric Biotechnol 3:296–302. doi:10.1016/j.bcab.2013.11.006
Bertóková A, Vikartovská A, Bučko M, Gemeiner P, Tkáč J, Chorvát D, Štefuca V, Neděla V (2015) Biooxidation of 2-phenylethanol to phenylacetic acid by whole-cell Gluconobacter oxydans biocatalyst immobilized in polyelectrolyte complex capsules. Biocatal Biotransform 33:111–120. doi:10.3109/10242422.2015.1053470
Bezbradica D, Obradovic B, Leskosek-Cukalovic I, Bugarski B, Nedovic V (2007) Immobilization of yeast cells in PVA particles for beer fermentation. Process Biochem 42:1348–1351. doi:10.1016/j.procbio.2007.04.009
Blažej M, Annus J, Markoš J (2004) Comparison of gassing-out and pressure-step dynamic methods for k L a measurement in an airlift reactor with internal loop. Chem Eng Res Des 82:1375–1382. doi:10.1205/cerd.82.10.1375.46737
Celik D, Bayraktar E, Mehmetoglu U (2004) Biotransformation of 2-phenylethanol to phenylacetaldehyde in a two-phase fed-batch system. Biochem Eng J 17:5–13. doi:10.1016/S1369-703X(03)00119-0
Chisti Y (1989) Airlift bioreactors. Elsevier Science Publishers, London
Freitas C, Teixeira JA (1997) Hydrodynamic studies in an airlift reactor with an enlarged degassing zone. Bioprocess Eng 18:267–279. doi:10.1007/s004490050441
Freitas C, Teixeira JA (2001) Oxygen mass transfer in a high solids loading three-phase internal-loop airlift reactor. Chem Eng J 84:57–61. doi:10.1016/S1385-8947(00)00274-6
Gandolfi R, Ferrara N, Molinari F (2001) An easy and efficient method for the production of carboxylic acids and aldehydes by microbial oxidation of primary alcohols. Tetrahedron Lett 42:513–514. doi:10.1016/S0040-4039(00)02008-6
Gandolfi R, Cavenago K, Gualandris R, Sinisterra Gago JV, Molinari F (2004) Production of 2-phenylacetic acid and phenylacetaldehyde by oxidation of 2-phenylethanol with free immobilized cells of Acetobacter aceti. Process Biochem 39:749–753. doi:10.1016/S0032-9592(03)00185-7
Grosová Z, Rosenberg M, Gdovin M, Sláviková L, Rebroš M (2009) Production of d-galactose using B-galactosidase and Saccharomyces cerevisiae entrapped in poly(vinylalcohol) hydrogel. Food Chem 116:96–100. doi:10.1016/j.foodchem.2009.02.011
Hua D, Xu P (2011) Recent advances in biotechnological production of 2-phenylethanol. Biotechnol Adv 29:654–660. doi:10.1016/j.biotechadv.2011.05.001
Hwang S-J, Lu W-J (1997) Gas–liquid mass transfer in an internal loop airlift reactor with low density particles. Chem Eng Sci 52:853–857
Jekel M, Buhr A, Willke T, Vorlop KD (1998) Immobilization of biocatalysts in LentiKats. Chem Eng Technol 21:275–278
Jin B, Yin P, Lant P (2006) Hydrodynamics and mass transfer coefficient in three-phase air-lift reactors containing activated sludge. Chem Eng Process 45:608–617. doi:10.1016/j.cep.2005.08.007
Juraščík M, Blažej M, Annus J, Markoš J (2006) Experimental measurements of volumetric mass transfer coefficient by the dynamic pressure-step method in internal loop airlift reactors of different scale. Chem Eng J 125:81–87. doi:10.1016/j.cej.2006.08.013
Molinari F, Gandolfi R, Aragozzini F, Leon R, Prazeres D (1999) Biotransformations in two-liquid-phase systems: production of phenylacetaldehyde by oxidation of 2-phenylethanol with acetic acid bacteria. Enzyme Microb Technol 25:729–735. doi:10.1016/S0141-0229(99)00107-6
Olivieri G, Marzocchella A, Salatino P (2003) Hydrodynamics and mass transfer in a lab-scale three-phase internal loop airlift. Chem Eng J 96:45–54. doi:10.1016/j.cej.2003.08.003
Rebroš M, Rosenberg M, Mlichová Z, Krištofíková Ľ, Paluch M (2006) A simple entrapment of glucoamylase into LentiKats® as an efficient catalyst for maltodextrin hydrolysis. Enzyme Microb Technol 39:800–804. doi:10.1016/j.enzmictec.2006.01.001
Rebroš M, Rosenberg M, Grosová Z, Krištofíková Ľ, Paluch M, Sipocz M (2009) Ethanol production from starch hydrolyzates using Zymomonas mobilis and glucoamylase entrapped in polyvinylalcohol hydrogel. Appl Biochem Biotechnol 158:561–570. doi:10.1007/s12010-008-8475-x
Schlieker M, Vorlop K-D (2006) A novel immobilization method for entrapment: LentiKats®. Immob Enzymes Cells Methods Biotechnol™ 22:333–343. doi:10.1007/978-1-59745-053-9_29
Stark D, Münch T, Sonnleitner B, Marison IW, von Stockar U (2002) Extractive bioconversion of 2-phenylethanol from l-phenylalanine by Saccharomyces cerevisiae. Biotechnol Prog 18:514–523. doi:10.1021/bp020006n
Trogl J, Bouskova A, Mrakota J, Pilarova V, Krudencova J, Mechurova J, Krizenecka S, Stloukal R (2011) Removal of nitrates from simulated ion-exchange brines with Paracoccus denitrificans encapsulated in Lentikats biocatalyst. Desalination 275:82–86. doi:10.1016/j.desal.2011.02.033
Vemmer M, Patel AV (2013) Review of encapsulation methods suitable for microbial biological control agents. Biol Control 67:380–389. doi:10.1016/j.biocontrol.2013.09.003
Vidová M, Slezáková I, Rebroš M, Krištofíková Ľ, Rosenberg M (2014) Gluconobacter oxydans used to production of natural aroma-2-phenylacetic acid in immobilized system (LentiKats form). New Biotechnol 31(Supplement):S91–S92. doi:10.1016/j.nbt.2014.05.1826
Villa R, Romano A, Gandolfi R, Sinisterra Gago JV, Molinari F (2002) Chemoselective oxidation of primary alcohols to aldehydes with Gluconobacter oxydans. Tetrahedron Lett 43:6059–6061. doi:10.1016/S0040-4039(02)01221-2
Vorlop, K. D. & Jekel, M. (2000). Process for preparing a biocatalyst with a polyvinyl alcohol gel and biocatalyst produced by this process. German patent DE 198 27 552
Wang CT, Sun BG, Cao YP, Wang J, Zhang H (2008) Biosynthesis of natural 2-phenylethanol by yeast cells. Modern Chem Ind 28:38–43
Wang H, Dong Q, Guan A, Meng C, Shi XA, Guo Y (2011) Synergistic inhibition effect of 2-phenylethanol and ethanol on bioproduction of natural 2-phenylethanol by Saccharomyces cerevisiae and process enhancement. J Biosci Bioeng 112:26–31. doi:10.1016/j.jbiosc.2011.03.006
Wenner W (1952) Phenylacetamide. Org Synth 4:760
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This work was supported by the Slovak Research and Development Agency under the contract No. APVV-0656-11 and by the grant VEGA 1/0687/16.
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Mihaľ, M., Červeňanský, I., Markoš, J. et al. Bioproduction of phenylacetic acid in airlift reactor by immobilized Gluconobacter oxydans . Chem. Pap. 71, 103–118 (2017). https://doi.org/10.1007/s11696-016-0062-y
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DOI: https://doi.org/10.1007/s11696-016-0062-y