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Catalysis in Green Chemistry and Engineering

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ISSN Print: 2572-9896

ISSN Online: 2572-990X

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A REVIEW ON FLAVOR ESTER SYNTHESIS USING IMMOBILIZED LIPASE

Volume 3, Issue 2, 2020, pp. 101-125
DOI: 10.1615/CatalGreenChemEng.2020035538
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ABSTRACT

The synthetic flavor esters have a fruity flavor and pleasant floral aroma and are broadly used in the food flavor and fragrance sector. With consumers' growing concern regarding health issues, chemical-free products are receiving more consideration in the food and flavor sector as compared to acid/base catalyzed products. Biocatalysis exhibits a distinct benefit in contrast to the chemical synthesis pathway when it comes to process operation, purity of the product, and decrease in the formation of side products. Thus, biocatalysis has drawn the attention of researchers for the synthesis of various value-added flavor esters, which have extensive applications in industries. Immobilized lipases are the effective enzymes used in bio-catalyzed synthesis as they can identify a broad diversity of substrates and catalyze vast reactions. This review presents the overview of the valuable flavor ester synthesis using the immobilized lipase. It summarizes the enzyme lipase, its properties, and the immobilization of enzymes for synthesis. The review also highlights reaction setup, reusability of the enzyme, the mechanism of lipase-catalyzed synthesis of the flavor ester, and enzyme kinetics study.

REFERENCES
  1. Abada, E.A.E., Production and Characterization of a Mesophilic Lipase Isolated from Bacillus stearothermophilus AB-1, Pak. J. Biol. Sci, vol. 11, pp. 1100-1106, 2008.

  2. Adams, T.B., Cohen, S.M., Doull, J., and Feron, V.J., The FEMA GRAS Assessment of Cinnamyl Derivatives Used as Flavor Ingredients, Food Chem. Toxicol., vol. 42, pp. 157-185, 2004.

  3. Akacha, N.B. and Gargouri, M., Microbial and Enzymatic Technologies Used for the Production of Natural Aroma Compounds: Synthesis, Recovery Modeling, and Bioprocesses, FoodBioprod. Process., vol. 94, pp. 675-709, 2015.

  4. Aljawish, A., Heuson, E., Bigan, M., and Froidevaux, R., Lipase Catalyzed Esterification of Formic Acid in Solvent and Solvent-Free Systems, Biocatal. Agric. Biotechnol., vol. 20, p. 101221, 2019.

  5. Antczak, S.M., Kubiak, A., Antczak, T., and Bielecki, S., Enzymatic Biodiesel Synthesis - Key Factors Affecting Efficiency of the Process, Renew. Energy, vol. 34, pp. 1185-1194, 2009.

  6. Ameri, A., Shakibaie, M., Khoobi, M., Faramarzi, M.A., Ameri, A., and Forootanfar, H., Immobilization of Thermoalkalophilic Lipase from BacillusatrophaeusFSHM2 on Amine-Modified Graphene Oxide Nanostructures: Statistical Optimization and Its Application for Pentyl Valerate Synthesis, Applied Biochemistry and Biotechnology, Appl. Biochem. Biotechnol., vol. 191, no. 2, pp. 579-604, 2020.

  7. Asmat, S. and Husain, Q., A Robust Nanobiocatalyst Based on High Performance Lipase Immobilized to Novel Synthesised Poly(o-Toluidine) Functionalized Magnetic Nanocomposite: Sterling Stability and Application, Mater. Sci. Eng., C, vol. 99, pp. 25-36,2019.

  8. Athawale, V., Manjrekar, N., and Athawale, M., Effect of Reaction Parameters on Synthesis of Citronellyl Methacrylate by Lipase-Catalyzed Transesterification, Biotechnol. Progr., vol. 19, no. 2, pp. 298-302,2003.

  9. Badgujar, K.C. and Bhanage, B.M., Enhanced Biocatalytic Activity of Lipase Immobilized on Biodegradable Copolymer of Chitosan and Polyvinyl Alcohol Support for Synthesis of Propionate Ester: Kinetic Approach, Ind. Eng. Chem. Res., vol. 53, no. 49, pp. 18806-18815,2014.

  10. Badgujar, K.C. and Bhanage, B.M., Thermo-Chemical Energy Assessment for Production of Energy-Rich Fuel Additive Compounds by Using Levulinic Acid and Immobilized Lipase, Fuel Process. Technol., vol. 138, pp. 139-146,2015.

  11. Badgujar, K.C. and Bhanage, B.M., The Green Metric Evaluation and Synthesis of Diesel Blend Compounds from Biomass Derived Levulinic Acid in Supercritical Carbon Dioxide, Biomass Bioenergy, vol. 84, pp. 12-21,2016.

  12. Badgujar, K.C., Sasaki, T., and Bhanage, B.M., Synthesis of Lipase Nano-Bioconjugates as an Efficient Biocatalyst: Characterization and Activity and Stability Studies with Potential Biocatalytic Applications, RSC Adv, vol. 5, no. 68, pp. 55238-55251, 2015.

  13. Badgujar, K.C., Pai, P.A., and Bhanage, B.M., Enhanced Biocatalytic Activity of Immobilized Pseudomonas cepacia Lipase under Sonicated Condition, Bioprocess. Biosyst. Eng., vol. 39, pp. 211-221, 2016.

  14. Bashir, N., Sood, M., and Bandral, J., Enzyme Immobilization and Its Applications in Food Processing: A Review, Int. J. Chem. Stud., vol. 8, pp. 254-261, 2020.

  15. Bayout, I., Bouzemi, N., Guo, N., Mao, X., Serra, S., Riva, S., and Secundo, F., Natural Flavor Ester Synthesis Catalyzed by Lipases, Flavour Fragrance J., vol. 35, no. 2, pp. 1-10, 2019.

  16. Berger, M. and Schneider, M.P., Lipases in Organic Solvents: The Fatty Acid Chain Length Profile, Biotechnol. Lett., vol. 13, pp. 641-645, 1991.

  17. Berger, R.G., Aroma Biotechnology, 1st ed., Heidelberg: Springer, pp. 31-74, 1995.

  18. Bezborodov, A.M. and Zagustina, N.A., Enzymatic Biocatalysis in Chemical Synthesis of Pharmaceuticals (Review), Appl. Biochem. Microbiol., vol. 52, pp. 237-249, 2016.

  19. Bezerra, M.A., Santelli, R.E., Oliveira, E.P., Villar, L.S., and Escaleira, L.A., Response Surface Methodology (RSM) as a Tool for Optimization in Analytical Chemistry, Talanta, vol. 76, no. 5, pp. 965-977, 2008.

  20. Bhavsar, K.V. and Yadav, G.D., Synthesis of Geranyl Acetate by Transesterification of Geraniol with Ethyl Acetate over Candida antarctica Lipase as Catalyst in Solvent-Free System, Flavour Fragrance J., vol. 34, pp. 288-293, 2019.

  21. Borgdorf, R. and Warwel, S., Substrate Selectivity of Various Lipases in the Esterification of Cis- and Trans-Octadecenoic Acid, Appl. Microbiol. Biotechnol, vol. 51, pp. 480-485, 1999.

  22. Carta, G., Gainer, L.J., and Gibson, M.E., Synthesis of Esters Using a Nylon-Immobilized Lipase in Batch and Continuous Reactors, Enzyme Microb. Technol., vol. 14, no. 11, pp. 904-910, 1992.

  23. Chang, R.C., Chou, S.J., and Shaw, J.F., Synthesis of Fatty Acid Esters in Recombinant Staphylococcus epidermidis Lipases in Aqueous Environment, J. Agric. Food Chem., vol. 49, pp. 2619-2622, 2001.

  24. Cihangir, N. and Sarikaya, E., Investigation of Lipase Production by a New Isolated of Aspergillus sp., World J. Microbiol. Biotechnol, vol. 20, pp. 193-197, 2004.

  25. Correa, L., Henriques, R.O., Rios, J.V., Lerin, J.A., de Oliveira, D., and Furigo, A., Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters, Appl. Biochem. Biotechnol., vol. 190, pp. 574-583, 2020.

  26. Derewenda, U., Brzozowski, A.M., Lawson, D.M., and Derewenda, Z.S., Catalysis at the Interface: The Anatomy of a Conformational Change in a Triglyceride Lipase, Biochemistry, vol. 31, no. 5, pp. 1532-1541, 1992.

  27. de Souza, M.C.M., dos Santos, K.P., Freire, R.M., Barreto, A., Fechine, P., and Goncalves, L., Production of Flavor Esters Catalyzed by Lipase B from Candida antarctica Immobilized on Magnetic Nanoparticles, Brazilian J. Chem. Eng., vol. 34, pp. 681-690, 2018.

  28. Duarte, N., Queiroz, D., Veloso, C., Castro, A., and Langone, M., Effects of Acetic Acid Addition Methods on Butyl Acetate Enzymatic Synthesis, Chem. Eng. Commun., vol. 207, no. 2. pp. 177-184,2020.

  29. Dubal, S., Tilkari, Y.P., Momin, S.A., and Borkar, I., Biotechnological Routes in Flavour Industries, Adv. Biotechnol, vol. 3, pp. 20-31,2008.

  30. Dutra, J.C.V., Terzi, S.C., Bevilaqua, J.V., Damaso, M.C.T., Couri, S., and Langone, M.A.P., Lipase Production in Solid State Fermentation Monitoring Biomass Growth of Aspergillus niger Using Digital Image Processing, Appl. Biochem. Biotechnol., vol. 147, pp. 63-75, 2008.

  31. Elias, N., Wahab, R.A., Chandren, S., Abdul Razak, F.I., and Jamalis, J., Effect of Operative Variables and Kinetic Study of Butyl Butyrate Synthesis by Candida rugosa Lipase Activated by Chitosan-Reinforced Nanocellulose Derived from Raw Oil Palm Leaves, Enzyme Microb. Technol, vol. 130, p. 109367, 2019.

  32. Escandell, J., Wurm, D.J., Belleville, M.P., Marcano, J.S., Harasek, M., and Jeanjean, D.P., Enzymatic Synthesis of Butyl Acetate in a Packed Bed Reactor under Liquid and Supercritical Conditions, Catal. Today, vol. 255, pp. 3-9,2015.

  33. FDA, Code of Federal Regulations, 21 CFR 172.515, Department of Health and Human Services, Food Additives Permitted for Direct Addition to Food for Human Consumption, Flavoring Agents and Related Substances, 2013.

  34. Ferraz, L.I.R., Possebom, G., Alvez, E.V., and Cansian, R.L., Application of Home-Made Lipase in the Production of Geranyl Propionate by Esterification of Geraniol and Propionic Acid in Solvent-Free System, Biocatal. Agric. Biotechnol., vol. 4, no. 1, pp. 44-48,2015.

  35. Gallage, N.J. and Maller, B.L., Vanillin-Bioconversion and Bioengineering of the Most Popular Plant Flavor and Its De Novo Biosynthesis in the Vanilla Orchid, Mol. Plant, vol. 8, pp. 40-57,2015.

  36. Gao, W., Wu, K., Chen, L., and Fan, H., A Novel Esterase from a Marine Mud Metagenomic Library for Biocatalytic Synthesis of Short-Chain Flavor Esters, Microb. Cell Fact., vol. 15, no. 1,p. 41,2016.

  37. Geng, B., Wang, M., Qi, W., and Su, R., Cinnamyl Acetate Synthesis by Lipasecatalyzed Transesterification in a Solvent-Free System, Biotechnol. Appl. Biochem., vol. 59, no. 4, pp. 270-275,2012.

  38. Ghislieri, D. and Turner, N.J., Biocatalytic Approaches to the Synthesis of Enantiomerically Pure Chiral Amines, Top. Catal, vol. 57, pp. 284-300,2014.

  39. Giunta, D., Sechi, B., and Solinas, M., Novozym-435 as Efficient Catalyst for the Synthesis of Benzoic and (Hetero) Aromatic Carboxylic Acid Esters, Tetrahedron, vol. 71, no. 18, pp. 2692-2697,2015.

  40. Gomes, N., Teixeira, J.A., and Belo, I., Fed-Batch versus Batch Cultures of Yarrowia Lipolytica for Gamma-Decalactone Production from Methyl Ricinoleate, Biotechnol. Lett., vol. 34, pp. 649-654,2012.

  41. Gomes Almeida Sa, A., Meneses, A.C., Araujo, P.H., and Oliveira, D., A Review on Enzymatic Synthesis of Aromatic Esters Used as Flavour Ingredients for Food, Cosmetics and Pharmaceuticals Industries, Trends Food Sci. Technol., vol. 69, pp. 95-105,2017.

  42. Gomes Almeida Sa, A., de Meneses, A.C., Lerin, L.A., de Araujo, P.H.H., Sayer, C., and de Oliveira, D., Biocatalysis of Aromatic Benzyl-Propionate Ester by Different Immobilized Lipases, Bioprocess. Biosyst. Eng., vol. 41, pp. 585-591, 2018.

  43. Griebeler, N., Polloni, A.E., Remonatto, D., Arbter, F., Vardanega, R., and Cechet, J.L., Isolation and Screening of Lipase Producing Fungi with Hydrolytic Activity, Food Bioprocess Technol., vol. 4, pp. 578-586, 2011.

  44. Gryglewicz, S., Jadownicka, E., and Czerniak, A., Lipase Catalysed Synthesis of Aliphatic, Terpene and Aromatic Esters by Alcoholysis in Solvent-Free Medium, Biotechnol. Lett., vol. 22, no. 17, pp. 1379-1382, 2000.

  45. Guncheva, M. and Zhiryakova, D., Catalytic Properties and Potential Applications of Bacillus Lipases, J. Mol. Catal. B: Enzym., vol. 68, pp. 1-21, 2011.

  46. Gunstone, F.D., Enzymes as Biocatalysts in the Modification of Natural Lipids, J. Sci. Food Agric., vol. 79, p. 1535, 1999.

  47. Gupta, A., Dhakate, S.R., Pahwa, M., Sinha, S., Chand, S., and Mathur, R.B., Geranyl Acetate Synthesis Catalyzed by Thermomyces lanuginosus Lipase Immobilized on Electrospun Polyacrylonitrile Nanofiber Membrane, Process Biochem., vol. 48, pp. 124-132, 2013.

  48. Gupta, R., Gupta, N., and Rathi, P., Bacterial Lipases: An Overview of Production, Purification and Biochemical Properties, Appl. Microbiol. Biotechnol, vol. 64, pp. 763-781,2004.

  49. He, S., Song, D., Chen, M., Haiming, C., Immobilization of Lipases on Magnetic Collagen Fibers and Its Applications for Short-Chain Ester Synthesis, Catalysts, vol. 7, p. 178,2017.

  50. Isah, A., Mahat, N., Jamalis, J., Attan, N., Zakaria, I.I., Huyop, F., and Wahab, R.A., Synthesis of Geranyl Propionate in a Solvent-Free Medium Using Rhizomucor Miehei Lipase Covalently Immobilized on Chitosan-Graphene Oxide Beads, Prep. Biochem. Biotechnol., vol. 47, no. 2, pp. 199-210,2016.

  51. Izci, A. and Hosmn,H.L., Kinetics of SynthesisofIsobutylPropionateoverAmberlyst-15, Turkish J. Chem., vol. 31,pp. 493-499, 2007.

  52. Jaeger, K.E. and Eggert, T., Lipases for Biotechnology, Curr. Opin. Biotechnol., vol. 13, no. 4, pp. 390-397,2002.

  53. Jaeger, K.E. and Reetz, M.T., Microbial Lipases form Versatile Tools for Biotechnology, Trends Biotechnol, vol. 16, no. 9, pp. 396-403,1998.

  54. Jaiswal, K.S. and Rathod, V.K., Acoustic Cavitation Promoted Lipase Catalyzed Synthesis of Isobutyl Propionate in Solvent Free System: Optimization and Kinetic Studies, Ultrason. Sonochem., vol. 40, pp. 727-735,2018.

  55. Jaiswal, K. and Rathod, V., Enzymatic Synthesis of Cosmetic Grade Wax Ester in Solvent Free System: Optimization, Kinetic and Thermodynamic Studies, SNAppl. Sci, vol. 1, no. 8, p. 949,2019.

  56. Jaiswal, K.J. and Rathod, V.K., Green Synthesis of Amyl Levulinate Using Lipase in the Solvent Free System: Optimization, Mechanism and Thermodynamics Studies, Catal. Today, In press, 2020.

  57. Jakoveti, L.N.D., Boskovi Vragolovi, N.M., and Bezbradica, D.I., Comparative Study of Batch and Fluidized Bed Bioreactors for Lipase-Catalyzed Ethyl Cinnamate Synthesis, Ind. Eng. Chem. Res., vol. 52, no. 47, pp. 16689-16697,2013.

  58. JECFA, Safety Evaluation of Certain Food Additives, Who Food Additives Series: 48, Prepared by the Fifty-Seventh Meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA), World Health Organization. Joint Expert Committee on Food Additives, 2001.

  59. Jiang, C. and Cheng, G., Optimization of Enzymatic Synthesis of Neryl Acetate in a Solvent Free System, OALIB, vol. 7, pp. 1-13, 2020.

  60. Khan, N.R. and Rathod, V.K., Enzyme Catalyzed Synthesis of Cosmetic Esters and Its Intensification: A Review, Process Biochem, vol. 50, pp. 1793-1806, 2015.

  61. Kim, H., Kim, T., Choi, N., Kim, B.H., Oh, S.W., and Kim, I.H., Synthesis of Diethylhexyl Adipate by Candida antarctica Lipase-Catalyzed Esterification, Process Biochem., vol. 78, pp. 58-62, 2019.

  62. Klibanov, A.M., Improving Enzymes by Using Them in Organic Solvents, Nature, vol. 409, pp. 241-246, 2001.

  63. Krings, C. and Berger, R.G., Biotechnological Production of Flavours and Fragrances, Appl. Microbiol. Biotechnol., vol. 8, p. 49, 1998.

  64. Kuo, C., Chen, G., Chen, C., and Liu, Y., Kinetics and Optimization of Lipasecatalyzed Synthesis of Rose Fragrance 2-Phenylethyl Acetate through Transesterification, Process Biochem., vol. 49, no. 3, pp. 437-444, 2014.

  65. Kuo, S.J. and Parkin, K.L., Substrate Preferences for Lipase Mediated Acyl-Exchange Reactions with Butteroil Are Concentration- Dependent, J. Am. Oil Chem. Soc., vol. 70, pp. 393-399, 1993.

  66. Laboret, F. and Perraud, R., Lipase-Catalyzed Production of Short-Chain Acids Terpenyl Esters of Interest to the Food Industry, Appl. Biochem. Biotechnol, vol. 82, no. 3, pp. 185-198, 1999.

  67. Lafuente, R.F., Lipase from Thermomyces lanuginosus: Uses and Prospects as an Industrial Biocatalyst, J. Mol. Catal. B: Enzym., vol. 62, p. 197, 2010.

  68. Li, C., Sun, J., Li, T., and Liu, S., Chemical and Enzymatic Synthesis of a Library of 2-Phenethyl Esters and Their Sensory Attributes, Food Chem., vol. 154, pp. 205-210,2014.

  69. Lima, L. de, Mendes, A.A., Lafuente, R., Tardioli, P.W., and Giordano, R., Performance of Different Immobilized Lipases in the Syntheses of Short- and Long-Chain Carboxylic Acid Esters by Esterification Reactions in Organic Media, Molecules, vol. 23, p. 766,2019.

  70. Lima-Ramos, J., Neto, W., and Woodley, J.M., Engineering of Biocatalysts and Biocatalytic Processes, Top. Catal., vol. 57, pp. 301-320,2014.

  71. Lomascolo, A., Lesage, M.L., Haon, M., Navarro, D., Antona, C., Faulds, C., and Marcel, A., Evaluation of the Potential of Aspergillus niger Species for the Bioconversion of L-Phenylalanine into 2-Phenylethanol, World J. Microbiol. Biotechnol., vol. 17, pp. 99-102, 2001.

  72. Long, K., Ghazali, H.M., Ariff, A., Che Man, Y., and Bucke, C., Substrate Preference of Mycelium-Bound Lipase from a Strain of AspergillusflavusLink, Biotechnol. Lett., vol. 20, pp. 369-372, 1998.

  73. Lozano, P., Enzymes in Neoteric Solvents: From One-Phase to Multiphase Systems, Green Chem., vol. 12, pp. 555-569, 2010.

  74. Manan, F., Attan, N., Widodo, N., Aboul-Enein, H., and Wahab, R., Rhizomucor Miehei Lipase Immobilized on Reinforced Chitosan-Chitin Nanowhiskers Support for Synthesis of Eugenyl Benzoate, Prep. Biochem. Biotechnol, vol. 48, pp. 92-102, 2017.

  75. Manohar, B. and Divakar, S., An Artificial Neural Network Analysis of Porcine Pancreas Lipase Catalysed Esterification of Anthranilic Acid with Methanol, Process Biochem., vol. 40, pp. 3372-3376,2005.

  76. Mahapatra, P., Kumari, A., Kumar Garlapati, V., Banerjee, R., and Nag, A., Enzymatic Synthesis of Fruit Flavor Esters by Immobilized Lipase from Rhizopus oligosporus Optimized with Response Surface Methodology, J. Mol. Catal. B: Enzym., vol. 60, nos. 1-2, pp. 57-63,2009.

  77. Matori, M., Asahara, T., and Ota, Y., Positional Specificity of Microbial Lipases, J Ferment. Bioeng, vol. 72, pp. 397-398,1991.

  78. Meneses, A.C. de, Almeida Sa, A.G., Lerin, L.A., Corazza, M.L., de Araujoa, P.H., Sayer, C., and Oliveira, D. de, Benzyl Butyrate Esterification Mediated by Immobilized Lipases: Evaluation of Batch and Fed-Batch Reactors to Overcome Lipase-Acid Deactivation, Process Biochem., vol. 78, pp. 50-57,2019a.

  79. Meneses, A.C. de, Lerin, L.A., Araujo,P.H.H., Sayer, C., andde Oliveira, D., Benzyl Propionate Synthesis by FedBatch Esterification Using Commercial Immobilized and Lyophilized Cal B Lipase, Bioprocess. Biosyst. Eng., vol. 42, no. 10, pp. 1625-1634, 2019b.

  80. Moentamaria, D., Dewajani, H., Chumaidi, A., Nurmahdi, H., and Sinduwati, C., Heterogenous Biocatalyst: Polyurethane Foam Coating Technique with Co-Immobilized Lipase for Bio-Flavor Production, IOP Conf. Series: Mater. Sci. Eng., vol. 732, p. 012003,2020.

  81. Monteiro, R., Neto, D.M., Fechine, P.B.A., Lopes, A.A.S., Goncalves, L.R.B., do Santos, J.C.S., de Souza, M.C.M., and Lafuente, R., Ethyl Butyrate Synthesis Catalyzed by Lipases A and B from Candida antarctica Immobilized onto Magnetic Nanoparticles. Improvement of Biocatalysts Performance under Ultrasonic Irradiation, Int. J. Mol. Sci, vol. 20, p. 5807, 2019.

  82. Moreira, W.C., Elias, A.L.P., Orio, W.R., and Padilha, G.S., Alternative Method to Improve the Ethyl Valerate Yield Using an Immobilised Burkholderia cepacia Lipase, J. Microencapsulation, vol. 36, pp. 327-337, 2019.

  83. Mukherjee, K.D., Lipase Catalysed Kinetic Resolution for the Fractionation of Fatty Acids and Other Lipids, Industrial Biocatalysis, C.T. Hou, Ed., Boca Raton, FL: CRC Press, pp. 5-1-29, 2005.

  84. Musa, N., Latip, W., Abd Rahman, R.N.Z., Salleh, A.B., and Mohamad Ali, M.S., Immobilization of an Antarctic Pseudomonas AMS8 Lipase for Low Temperature Ethyl Hexanoate Synthesis, Catalysts, vol. 8, p. 234, 2018.

  85. Oliveira, U.M.F. de, Lima de Matos, L.J.B., Souza, M.C.M. de, Pinheiro, B.B., dos Santos, J.C.S., and Goncalves, L.R.B., Efficient Biotechnological Synthesis of Flavor Esters Using a Low-Cost Biocatalyst with Immobilized Rhizomucor miehei Lipase, Mol. Biol. Rep., vol. 46, pp. 597-608, 2019.

  86. Onoja, E., Chandren, S., Abdul Razak, F.I., and Abdul Wahab, R., Enzymatic Synthesis of Butyl Butyrate by Candida rugosa Lipase Supported on Magnetized-Nanosilica from Oil Palm Leaves: Process Optimization, Kinetic and Thermodynamic Study, J. Taiwan Inst. Chem. Eng., vol. 91, pp. 105-118, 2018.

  87. Padilha, G., Tambourgi, E., and Alegre, R., Evaluation of Lipase from Burkholderia cepacia Immobilized in Alginate Beads and Application in the Synthesis of Banana Flavor (Isoamyl Acetate), Chem. Eng. Commun., vol. 205, p. 10, 2017.

  88. Pereira, G.N., Holz, J.P., Giovannini, P., and Oliveira, J.V., Enzymatic Esterification for the Synthesis of Butyl Stearate and Ethyl Stearate, Biocatal. Agric. Biotechnol., vol. 16, pp. 373-377, 2018.

  89. Ribeiro, B.D., de Castro, A.M., Coelho, M.A.Z., and Freire, D.M.G., Production and Use of Lipases in Bioenergy: A Review from the Feedstocks to Biodiesel Production, Enzyme Res, vol. 2011, p. 615803, 2011.

  90. Rodrigues, R.C., Volpato, G., Wada, K., and Ayub, M.A.Z., Enzymatic Synthesis of Biodiesel from Transesterification Reactions of Vegetable Oils and Short Chain Alcohols, J. Am. Oil Chem. Soc., vol. 82, p. 925, 2008.

  91. Rogalska, E., Cudrey, C., Ferrato, F., and Verger, R., Stereoselective Hydrolysis of Triglycerides by Animal and Microbial Lipases, Chirality, vol. 5, pp. 24-30, 1993.

  92. Sankaran, R., Show, P.L., and Chang, J.S., Biodiesel Production Using Immobilized Lipase: Feasibility and Challenges, Biofuels, Bioprod. Biorefin., vol. 10, no. 6, pp. 896-916, 2016.

  93. Salvi, H.M., Kamble, M.P., and Yadav, G.D., Synthesis of Geraniol Esters in a Continuous-Flow Packed-Bed Reactor of Immobilized Lipase: Optimization of Process Parameters and Kinetic Modeling, Appl. Biochem. Biotechnol., vol. 184, no. 2, pp. 630-643,2018.

  94. Santos, P., Zabot, G.L., Meireles, M.A.A., and Mazutti, M.A., Synthesis of Eugenyl Acetate by Enzymatic Reactions in Supercritical Carbon Dioxide, Biochem. Eng. J., vol. 114, pp. 1-9,2016.

  95. Sarno, M.C., Iuliano, M., Polichetti, M., and Ciambelli, P., High Activity and Selectivity Immobilized Lipase on Fe3O4 Nanoparticles for Banana Flavour Synthesis, Process Biochem, vol. 56, pp. 98-108,2017.

  96. Silva, N.C.A., Miranda, J.S., Bolina, I.C.A., and Silva, W.C, Immobilization of Porcine Pancreatic Lipase on Poly-Hydroxybutyrate Particles for the Production of Ethyl Esters from Macaw Palm Oils and Pineapple Flavor, Biochem. Eng. J., vol. 82, pp. 1139-1149,2014.

  97. Simone, G. de, Menchise, V., and Alterio, V., The Crystal Structure of an EST2 Mutant Unveils Structural Insights on the H Group of the Carboxylesterase/Lipase Family, J. Mol. Biol., vol. 343, no. 1, pp. 137-146,2004.

  98. Sharma, C.K., Chauhan, G.S., and Kanwar, S.S., Synthesis of Medically Important Ethyl Cinnamate Ester by Porcine Pancreatic Lipase Immobilized on Poly (AAc-co-HPMA-cl-EGDMA) Hydrogel, J. Appl. Polym. Sci., vol. 121, pp. 2674-2679,2011.

  99. Shin, M., Seo, J., Baek, Y., Lee, T., Jang, M., and Park, C., Novel and Efficient Synthesis of Phenethyl Formate via Enzymatic Esterification of Formic Acid, Biomolecul., vol. 10, no. 1, p. 70,2020.

  100. Sonnet, P.E., Lipase Selectivities, J. Am. Oil Chem. Soc, vol. 65, pp. 900-905,1998.

  101. Sugawara, A., Matsui, D., Yamada, M., Asano, Y., and Isobe, K., Characterization of Two Amine Oxidases from Aspergillus carbonarius AIU 205, J. Biosci. Bioeng., vol. 119, pp. 629-635,2015.

  102. Sun, H., Zhang, H., Ang, E.L., and Zhao, H., Biocatalysis for the Synthesis of Pharmaceuticals and Pharmaceutical Intermediates, Bioorg. Med. Chem., vol. 26, no. 7, pp. 1275-1284,2018.

  103. Thakur, S., Lipases, Its Sources, Properties and Applications: A Review, Int. J. Eng. Res., vol. 3, p. 7,2012.

  104. Tomke, P. and Rathod, V.K., A Novel Step Towards Immobilization of Biocatalyst Using Agro Waste and Its Application for Ester Synthesis, Int. J. Biol. Macromol., vol. 117, pp. 366-376,2018.

  105. Tran, D.T., Chen, C.L., and Chang, J.S., Continuous Biodiesel Conversion via Enzymatic Transesterification Catalyzed by Immobilized Burkholderia Lipase in a Packed-Bed Bioreactor, Appl. Energy, vol. 168, pp. 340-350,2016.

  106. Tyndall, J.D., Sinchaikul, S., Fothergill-Gilmore, L.A., Taylor, P., and Walkinshaw, M.D., Crystal Structure of a Thermostable Lipase from Bacillus stearothermophilus P1, J. Mol. Biol, vol. 323, no. 5, pp. 859-869,2002.

  107. Vakhlu, J. and Kour, A., Yeast Lipases: Enzyme Purification, Biochemical Properties and Gene Cloning, Electron. J. Biotechnol., vol. 9, pp. 1-17, 2006.

  108. Vandamme, E.J. and Soetaert, W., Bioflavours and Fragrances via Fermentation and Biocatalysis, J. Chem. Technol. Biotechnol, vol. 77, pp. 1323-1332,2002.

  109. Vanin, A.B., Orlando, T., Piazza, S.P., and Puton, B.M.S., Antimicrobial and Antioxidant Activities of Clove Essential Oil and Eugenyl Acetate Produced by Enzymatic Esterification, Appl. Biochem. Biotechnol, vol. 174, no. 4, pp. 1286-1298,2010.

  110. Vasilescu, C., Todeaa, A., Nanb, A., Circub, M., Turcub, R., Beneaa, I.C., and Petera, F., Enzymatic Synthesis of Short-Chain Flavor Esters from Natural Sources Using Tailored Magnetic Biocatalysts, Food Chem., vol. 296, pp. 1-8,2019.

  111. Waghmare, G., Chatterji, A., and Rathod, V.K., Kinetics of Enzymatic Synthesis of Cinnamyl Butyrate by Immobilized Lipase, Appl. Biochem. Biotechnol, vol. 183, pp. 792-806,2017.

  112. Wang, L., Chi, Z.M., Wang, X.H., Liu, Z.Q., and Li, J., Diversity of Lipase-Producing Yeasts from Marine Environments and Oil Hydrolysis by Their Crude Enzymes, Ann. Microbiol., vol. 4, pp. 2-7,2007.

  113. Weber, D., Nascimentoa, M., and Parizeb, A.L., Immobilization of Burkholderia cepacia Lipase on Crosslinked Chitosan-Based Support for the Synthesis of Geranyl Acetate, Biocatal. Agric. Biotechnol., vol. 19, p. 101133,2019.

  114. Wohlgemuth, R.,Biocatalysis-Key to Sustainable Industrial Chemistry, Curr. Opin. Biotechnol., vol. 21, no. 6, pp. 713-724,2010.

  115. Wolfson, W., In the Fragrance Business, the Right Molecule Smells Like Money, Chem. Biol., vol. 12, no. 8, pp. 857-858,2005.

  116. Woodcock, L.L., Wiles, C., Greenway, G.M., Watts, P., Wells, A., and Eyley, S., Enzymatic Synthesis of a Series of Alkyl Esters Using Novozyme 435 in a Packed-Bed, Miniaturized, Continuous Flow Reactor, Biocatal. Biotransform., vol. 26, no. 6, pp. 466-472, 2008.

  117. Xiaoshuan, L., Dinghua, Y., Wengui, Z., Zhengwen, L., Zhang, X., and Huang, H., Effective Synthesis of cis-3-hexen-1-yl Acetate via Transesterification over KOH/y-Al2O3: Structure and Catalytic Performance, Appl. Catal, A, vol. 455, pp. 1-7,2013.

  118. Xu, Y., Nordblad, M., and Woodley, J.M., A Two-Stage Enzymatic Ethanol-Based Biodiesel Production in a Packed Bed Reactor, J. Biotechnol, vol. 162, pp. 407-414,2012.

  119. Yadav, G.D. and Dhoot, S.B., Immobilized Lipase-Catalysed Synthesis of Cinnamyl Laurate in Non-Aqueous Media, J. Mol. Catal. B: Enzym., vol. 57, pp. 34-39,2009.

  120. Yadav, G.D. and Kamble, M., A Green Process for Synthesis of Geraniol Esters by Immobilized Lipase from Candida antarctica B Fraction in Non-Aqueous Reaction Media: Optimization and Kinetic Modeling, Int. J. Chem. Reactor Eng., vol. 16, p. 7, 2018.

  121. Yildirim, D., Baran, E., Ates, S., Yazici, B., and Tukel, S.S., Improvement of Activity and Stability of Rhizomucor miehei Lipase by Immobilization on Nanoporous Aluminium Oxide and Potassium Sulfate Microcrystals and Their Applications in the Synthesis of Aroma Esters, Biocatal. Biotransform., vol. 37, no. 3, pp. 210-223,2019.

  122. Zaks, A. andKlibanov, A.M., Enzymatic Catalysis in Nonaqueous Solvents, J. Biol. Chem, vol. 263, pp. 3194-3201,1988.

  123. Zhang, J., Fang, X., Zhu, X.-L., Li, Y., Xu, H.P., Zhao, B.-F., Chen, L., and Zhang, X.D., Microbial Lipid Production by the Oleaginous Yeast Cryptococcus curvatus O3 Grown in Fed-Batch Culture, Biomass Bioenergy, vol. 35, p. 1911,2011.

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  1. Vilas Bôas Renata N., Castro Heizir F., A review of synthesis of esters with aromatic, emulsifying, and lubricant properties by biotransformation using lipases, Biotechnology and Bioengineering, 119, 3, 2022. Crossref

  2. Zieniuk Bartłomiej, Białecka-Florjańczyk Ewa, Wierzchowska Katarzyna, Fabiszewska Agata, Recent advances in the enzymatic synthesis of lipophilic antioxidant and antimicrobial compounds, World Journal of Microbiology and Biotechnology, 38, 1, 2022. Crossref

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