Novelty of Penicillium camembertii Lipase Supported on Glutaraldehyde Activated-SBA-15 Mesoporous Silica for Mono-Esterification of Bioglycerol in Non-Aqueous Media
-
Moreshwar P. Hude
Abstract
Hexagonal mesoporous type silica SBA-15 with pore sizes in the range 5.0–8.3 nm was synthesized using non-ionic triblock copolymer and characterized by Accelerated Surface Area Porosimetry (ASAP), FT-IR spectroscopy, X-ray diffraction (XRD) and Scanning Electron Microscopy (SEM). Different lipases were immobilized in glutaraldehyde activated mesoporous SBA-15 support. The resulting supported enzymes were shown to be active and stable catalysts for esterification of glycerol with oleic acid to produce monoglyceride (MG) which is commonly used in food industry. Various parameters were studied systematically to study kinetics. MG Synthesis using enzymatic process is an environmentally friendly approach. Enzyme immobilized on SBA-15 showed the best stability and catalytic activity in organic solvents. Out of various lipases studied penicillium camembertii (Lipase G) produced MG efficiently at low temperature. Reusability was studied on immobilized enzymes. Immobilized lipase maintained 90 % of its esterification activity in non-aqueous media even after 4 cycles of use. The selectivity of Lipase G is found to be 98 % for monoacylglyceride.
Funding statement: Funding: Department of Biotechnology, Govt of India; Graduate Exchange Programme, University of Saskatchewan, Canada
Acknowledgements
G.D.Y. received support from R.T. Mody Distinguished Professor Endowment and J. C. Bose National Fellowship of Department of Science and Technology, Government of India. MPH thanks Department of Biotechnology (DBT) Govt. of India for Research fellowship and Graduate Students Exchange programme, University of Saskatchewan, Canada. We thank Amano Enzymes (Japan) for free enzyme samples.
References
1. Adi, W., Christina, D., Yoram S., 2007. Glycerol as a Green Solvent for High Product Yields and Selectivities. Environ. Chem. Lett. 5, 67–71.10.1007/s10311-006-0080-zSearch in Google Scholar
2. Bautista, L.F., Morales, G., Sanz, R., 2010. Immobilization Strategies for Laccase from Trametes Versicolor on Mesostructured Silica Materials and the Application to the Degradation of Naphthalene. Bioresour. Technol. 101, 8541–8548.10.1016/j.biortech.2010.06.042Search in Google Scholar
3. Bradford, M.M., 1976. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 72, 248–254.10.1016/0003-2697(76)90527-3Search in Google Scholar
4. Chaubey, A., Parshad, R., Koul, S., Taneja, S.C., Qazi, G.N., 2006. Enantioselectivity Modulation through Immobilization of Arthrobacter sp. Lipase: Kinetic Resolution of Fluoxetine Intermediate. J. Mol. Catal. B: Enzym. 42, 39–44.10.1016/j.molcatb.2006.06.011Search in Google Scholar
5. D’Souza, S.F., 1999. Immobilized Enzymes in Bioprocess. Curr. Sci. 77, 67–79.Search in Google Scholar
6. Gervásio, P. S., Matthias, M., Jonas, C., 2009. Glycerol: A Promising and Abundant Carbon Source for Industrial Microbiology. Biotechnol. Adv. 27, 30–39.10.1016/j.biotechadv.2008.07.006Search in Google Scholar
7. Humphrey, H.P., Wright, P.A., Botting, N.P., 2001. Enzyme Immobilization Using Siliceous Mesoporous Molecular Sieves. Micro. Meso. Mater. 44–45, 763–768.10.1016/S1387-1811(01)00258-XSearch in Google Scholar
8. Ihara, F., Kageyama, Y., Hirata, M., Nihira, T., Yamada, Y., 1991. Purification, Characterization, and Molecular Cloning of Lactonizing Lipase from Pseudomonas Species. J. Biol. Chem. 266, 18135–18138.10.1016/S0021-9258(18)55246-7Search in Google Scholar
9. Macario, A., Katovic, A., Giordano, G., Forni, L., Carloni, F., Filippini, A., Setti, L., 2005. Immobilization of Lipase on Microporous and Mesoporous Materials: Studies of the Support Surfaces. Stud. Surf. Sci. Catal. 155, 381–394.10.1016/S0167-2991(05)80166-1Search in Google Scholar
10. Mario, P., Rosaria C., Hiroshi, K., 2009. Recent Advances in the Conversion of Bioglycerol into Value-Added Products. Eur. J. Lipid Sci. Technol. 111, 788–799.10.1002/ejlt.200800210Search in Google Scholar
11. Mario, P., Rosaria, C., Hiroshi, K., Michele, R., Cristina D.P., 2007. From Glycerol to Value Added Products. Angew. Chem. Int. Ed. 46, 4434–4440.10.1002/anie.200604694Search in Google Scholar PubMed
12. Mateo, C., Palomo, J., Lorente, G., Guisan, J., Lafuente, R., 2007. Improvement of Enzyme Activity, Stability and Selectivity via Immobilization Techniques. Enzyme Microb. Technol. 40, 1451–1463.10.1016/j.enzmictec.2007.01.018Search in Google Scholar
13. O‘Neill, S.P., Dunnill, P., Lilly, M.D., 1971. A Comparative Study of Immobilized Amyloglucosidase in a Packed Bed Reactor and a Continuous Feed Stirred Tank Reactor. Biotechnol. Bioeng. 13, 337–352.10.1002/bit.260130302Search in Google Scholar PubMed
14. Pinsirodoma, P., Watanabeb, Y., Nagao, T., Sughihara, A., Kobayashi, T., 2004. Critical Temperature for Production of MAG by Esterification of Different FA with Glycerol Using Penicillium camembertii Lipase. J. Am. Oil. Chem. Soc. 81, 543–547.10.1007/s11746-006-0938-zSearch in Google Scholar
15. Siliang, G., Yujun, W., Xiang, D., Guangsheng, L., Youyuan, D., 2010. Effect of Pore Diameter and Cross-Linking Method on the Immobilization Efficiency of Candida Rugosa Lipase in SBA-15. Bioresour. Technol. 101, 3830–3837.10.1016/j.biortech.2010.01.023Search in Google Scholar PubMed
16. Soares, C.M.F., Santana, M., Zanin, G., De Castro, H., 2003. Covalent Coupling Method for Lipase Immobilization on Controlled Pore Silica in the Presence of Nonenzymatic Proteins. Biotechnol. Prog. 19, 803–807.10.1021/bp025779qSearch in Google Scholar PubMed
17. Sonntag, N., 1981. Glycerolysis of Fats and Methyl Esters -Status, Review and Critique. J. Am. Oil. Chem. Soc. 59,795–802.10.1007/BF02634442Search in Google Scholar
18. Tiwari M.S., Yadav G.D., 2015, Kinetics of Friedel-Craft Benzoylation of Veratrole with Benzoic Anhydride Using Cs2.5-H0.5PW12O40/K-10 Acid Catalyst. Chem. Eng. J. 266,64–73.10.1016/j.cej.2014.12.043Search in Google Scholar
19. White, J.S., White, D.C., 1997. Source Book of Enzymes, CRC Press, Boca Raton, FL, 1008.Search in Google Scholar
20. Yadav, G.D., Borkar, IV., 2006. Kinetic Modeling of Microwave Assisted Chemo-Enzymatic Epoxidation of Styrene to Styrene Oxide. AICh E. J. 52, 1235–1247.10.1002/aic.10700Search in Google Scholar
21. Yadav, G.D., Borkar, I.V., 2009. Kinetic and Mechanistic Investigation of Microwave- Assisted Lipase Catalyzed Synthesis of Citronellyl Acetate. Ind. Eng. Chem. Res. 48, 7915–7922.10.1021/ie800591cSearch in Google Scholar
22. Yadav, G.D., Chandan, P.A., Gopalaswami, N., 2012. Green Etherification of Bioglycerol with 1-Phenyl Ethanol Over Supported Heteropolyacid. Clean. Tech. Environ. Policy 14, 85–95.10.1007/s10098-011-0380-2Search in Google Scholar
23. Yadav, G.D., Devi, K.M., 2004. Immobilized Lipase-Catalysed Esterification and Transesterification Reactions in Non-Aqueous Media for the Synthesis of Tetrahydrofurfuryl Butyrate: Comparison and Kinetic Modeling. Chem. Eng. Sci. 59, 373–383.10.1016/j.ces.2003.09.034Search in Google Scholar
24. Yadav, G.D., Jadhav, S.S., 2005. Synthesis of Reusable Lipases by Immobilization on Hexagonal Mesoporous Silica and Encapsulation in Calcium Alginate: Transesterification in Non-Aqueous Medium. Micropor Mesopor Mater 86, 215–222.10.1016/j.micromeso.2005.07.018Search in Google Scholar
25. Yadav, G.D., Jadhav, S.S., 2007. Synthesis of Novel Supports for Enzymes: Transesterification of p-Chlorobenzyl Alcohol with Vinyl Acetate in Non-aqueous Media and Kinetic Modelling. Ind. Chem. Eng. 49,283–295.Search in Google Scholar
26. Yadav, G.D., Lathi, P.S., 2003. Kinetics and Mechanism of Synthesis of Butyl Isobutyrate Over Immobilized Lipases. Biochem. Eng. J. 16, 245–252.10.1016/S1369-703X(03)00026-3Search in Google Scholar
27. Yadav, G.D., Lathi, P.S., 2006. Intensification of Enzymatic Synthesis of Propylene Glycol Monolaurate from 1, 2-Propanediol and Lauric Acid Under Microwave Irradiation: Kinetics of Forward and Reverse Reactions. Enzyme Microb. Technol. 38, 814–820.10.1016/j.enzmictec.2005.08.013Search in Google Scholar
28. Yadav, G.D., Sajgure, A.D., 2007. Synergism of Microwave Irradiation and Enzyme Catalysis in Synthesis of Isoniazid. J. Chem. Technol. Biotechnol. 82, 964–970.10.1002/jctb.1738Search in Google Scholar
29. Yadav, G.D., Sajgure, A.D., Dhoot, S.B., 2007. Enzyme catalysis in fine chemical and pharmacuetical industries, in Sanjoy K. Bhattacharya (Ed.), Enzyme Mixtures and Complex Biosynthesis. Landes Biosciences, Austin, TX.Search in Google Scholar
30. Yadav, G.D., Sajgure, A.D., Dhoot, S.B., 2008. Insight into Microwave Irradiation and Enzyme Catalysis in Enantioselective Resolution of RS-(±)-Methyl Mandelate. J. Chem. Technol. Biotechnol. 83, 1145–1153.10.1002/jctb.1975Search in Google Scholar
31. Yadav, G.D., Trivedi, A.H., 2003. Kinetic Modeling of Immobilized-Lipase Catalyzed Transesterification of n-Octanol with Vinyl Acetate in Non-Aqueous Media. Enzyme Microb. Technol. 32, 783–789.10.1016/S0141-0229(03)00064-4Search in Google Scholar
32. Zhao, J., Wang, Y., Luo, G., Zhu, S., 2011. Immobilization of Penicillin G Acylase on Macro-Mesoporous Silica Spheres. Bioresour. Technol. 102, 529–535.10.1016/j.biortech.2010.09.076Search in Google Scholar PubMed
Supplemental Material
The online version of this article (DOI: 10.1515/ijcre-2014-0058) offers supplementary material, available to authorized users.
©2016 by De Gruyter
Articles in the same Issue
- Frontmatter
- Editorial
- In Honour of Professor Serge Kaliaguine
- Research Articles
- Adsorptive Removal of Nitrogen and Sulfur Containing Compounds by SBA15 Supported Nickel (II) and Tungsten Phosphides and the Adsorption Mechanisms
- Study of Cu-Zn and Au/TiO2 Catalysts on Anodized Aluminum Monoliths for Hydrogen Generation and Purification
- Electrocatalytic Activity of Three Carbon Materials for the In-situ Production of Hydrogen Peroxide and Its Application to the Electro-Fenton Heterogeneous Process
- Graphitic Carbon Nitride-Titanium Dioxide Nanocomposite for Photocatalytic Hydrogen Production under Visible Light
- Simulation of the Selective Hydrogenation of C3-Cut in the Liquid Phase
- On a Rational Performance Evaluation for the Development of Inorganic Membrane Technology in Gas Separation and Membrane Reactors
- Equilibrium and Kinetics of Methane and Ethane Adsorption in Carbon Molecular Sieve
- Synthesis of Mesoporous Tungsten Oxide/γ-Alumina and Surfactant-Capped Tungsten Oxide Nanoparticles and Their Catalytic Activities in Oxidative Cleavage of Oleic Acid
- Comparative Study of Quick Lime and CaO as Catalysts of Safflower Oil Transesterification
- Novelty of Penicillium camembertii Lipase Supported on Glutaraldehyde Activated-SBA-15 Mesoporous Silica for Mono-Esterification of Bioglycerol in Non-Aqueous Media
- Kinetics of Transesterification of Safflower Oil to Obtain Biodiesel Using Heterogeneous Catalysis
- Whole Cell Bioconversion of (+)-valencene to (+)-nootkatone in 100 % Organic Phase using Yarrowia lipolytica 2.2ab
Articles in the same Issue
- Frontmatter
- Editorial
- In Honour of Professor Serge Kaliaguine
- Research Articles
- Adsorptive Removal of Nitrogen and Sulfur Containing Compounds by SBA15 Supported Nickel (II) and Tungsten Phosphides and the Adsorption Mechanisms
- Study of Cu-Zn and Au/TiO2 Catalysts on Anodized Aluminum Monoliths for Hydrogen Generation and Purification
- Electrocatalytic Activity of Three Carbon Materials for the In-situ Production of Hydrogen Peroxide and Its Application to the Electro-Fenton Heterogeneous Process
- Graphitic Carbon Nitride-Titanium Dioxide Nanocomposite for Photocatalytic Hydrogen Production under Visible Light
- Simulation of the Selective Hydrogenation of C3-Cut in the Liquid Phase
- On a Rational Performance Evaluation for the Development of Inorganic Membrane Technology in Gas Separation and Membrane Reactors
- Equilibrium and Kinetics of Methane and Ethane Adsorption in Carbon Molecular Sieve
- Synthesis of Mesoporous Tungsten Oxide/γ-Alumina and Surfactant-Capped Tungsten Oxide Nanoparticles and Their Catalytic Activities in Oxidative Cleavage of Oleic Acid
- Comparative Study of Quick Lime and CaO as Catalysts of Safflower Oil Transesterification
- Novelty of Penicillium camembertii Lipase Supported on Glutaraldehyde Activated-SBA-15 Mesoporous Silica for Mono-Esterification of Bioglycerol in Non-Aqueous Media
- Kinetics of Transesterification of Safflower Oil to Obtain Biodiesel Using Heterogeneous Catalysis
- Whole Cell Bioconversion of (+)-valencene to (+)-nootkatone in 100 % Organic Phase using Yarrowia lipolytica 2.2ab
