A novel hybrid biocatalyst from immobilized Eversa^® Transform 2.0 lipase and its application in biolubricant synthesis

References

• Abifarin JK, Prakash C, Singh S. 2022. Optimization and significance of fabrication parameters on the mechanical properties of 3D printed Chitosan/PLA scaffold. Mater Today Proc. 50(5):2018–2025.
   Google Scholar
• Aghaei H, Yasinian A, Taghizadeh A. 2021. Covalent immobilization of lipase from Candida rugosa on epoxy-activated cloisite 30B as a new heterofunctional carrier and its application in the synthesis of banana flavor and production of biodiesel. Int J Biol Macromol. 178:569–579.
   PubMed Web of Science ®Google Scholar
• Aguieiras ÉCG, Cavalcanti EDC, Da Silva PR, Soares VF, Fernandez-Lafuente R, Bessa Assunção CL, Da Silva JAC, Freire, DM. 2020. Enzymatic synthesis of neopentyl glycol-bases biolubricants using biodiesel from soybean and castor bean as raw materials. Renew Energy. 148:689–696.
   Web of Science ®Google Scholar
• Alafaghani A, Qattawi A. 2018. Investigating the effect of fused deposition modeling processing parameters using Taguchi design of experiment method. J Manuf Process. 36:164–174.
   Web of Science ®Google Scholar
• Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ. 1990. Basic local alignment search tool. J Mol Biol. 215:403–410.
   PubMed Web of Science ®Google Scholar
• Attia NK, El-Mekkawi SA, Elardy OA, Abdelkader EA. 2020. Chemical and rheological assessment of produced biolubricants from different vegetable oils. Fuel. 271:117578.
   Web of Science ®Google Scholar
• Balali S, Davachi SM, Sahraeian R, Shiroud Heidari B, Seyfi J, Hejazi I. 2018. Preparation and characterization of composite blends based on polylactic acid/polycaprolactone and silk. Biomacromolecules. 19(11):4358–4369.
   PubMed Web of Science ®Google Scholar
• Barbosa MS, Freire CCC, Brandão LMS, Pereira EB, Mendes AA, Pereira MM, Lima ÁS, Soares, CMF. 2021. Biolubricant production under zero-waste Moringa oleifera Lam biorefinery approach for boosting circular economy. Ind Crops Prod. 167:113542.
   Web of Science ®Google Scholar
• Barbosa O, Ortiz C, Berenguer-Murcia Á, Torres R, Rodrigues RC, Fernandez-Lafuente R. 2014. Glutaraldehyde in bio-catalysts design: a useful crosslinker and a versatile tool in enzyme immobilization. RSC Adv. 4(4):1583–1600.
   Web of Science ®Google Scholar
• Bayramoglu G, Celikbicak O, Kilic M, Yakup Arica M. 2022. Immobilization of Candida rugosa lipase on magnetic chitosan beads and application in flavor esters synthesis. Food Chem. 366:130699.
   PubMed Web of Science ®Google Scholar
• Bedoya OF, Tischer I. 2015. Detección de homología remota de proteínas usando modelos 3D enriquecidos con propiedades fisicoquímicas. Ingeniería. 17(1):75–84.
   Google Scholar
• Ben Hlima H, Dammak M, Karray A, Drira M, Michaud P, Fendri I, Abdelkafi S. 2021. Molecular and structural characterizations of lipases from Chlorella by functional genomics. Mar Drugs. 19(2):70.
   PubMed Web of Science ®Google Scholar
• Benítez-Mateos AI, Contente ML. 2021. Agarose vs. methacrylate as material supports for enzyme immobilization and continuous processing. Catalysts. 11(7):814.
   Web of Science ®Google Scholar
• Bering L, Thompson J, Micklefield J. 2022. New reaction pathways by integrating chemo- and biocatalysis. Trends Chem. 4(5):392–408. https://doi.org/10.1016/j.trechm.2022.02.008
   Google Scholar
• Bezerra FDA, Lima GDC, Carvalho ACLDM, Vega KB, Oliveira MCF, de Lemos TLG, dos Santos JCS, Gonçalves LRB, Rios NS, Fernandez-Lafuente R, et al. 2022. Chemoenzymatic synthesis of both enantiomers of propafenone hydrochloride through lipase-catalyzed process. Molecular Catalysis. 529:112540.
   Web of Science ®Google Scholar
• Bezerra RM, Monteiro RRC, Neto DMA, da Silva FFM, de Paula RCM, de Lemos TLG, Fechine PBA, Correa MA, Bohn F, Gonçalves LRB, et al. 2020. A new heterofunctional support for enzyme immobilization: PEI functionalized Fe3O4 MNPs activated with divinyl sulfone. Application in the immobilization of lipase from Thermomyces lanuginosus. Enzyme Microb Technol. 138:109560.
   PubMed Web of Science ®Google Scholar
• Bickerstaff GF. 2003. Immobilization of enzymes and cells: some practical considerations. Immobil Enzym Cells. 1:1–12.
   Google Scholar
• Bilal M, Iqbal HMN. 2019. Naturally-derived biopolymers: potential platforms for enzyme immobilization. Int J Biol Macromol. 130:462–482.
   PubMed Web of Science ®Google Scholar
• Bolina ICA, Gomes RAB, Mendes AA. 2021. Biolubricant production from several oleaginous feedstocks using lipases as catalysts: current scenario and future perspectives. Bioenergy Res. 14:1039–1057.
   Web of Science ®Google Scholar
• Bonazza HL, Manzo RM, dos Santos JCS, Mammarella EJ. 2018. Operational and thermal stability analysis of Thermomyces lanuginosus lipase covalently immobilized onto modified chitosan supports. Appl Biochem Biotechnol. 184(1):182–196.
   PubMed Web of Science ®Google Scholar
• Bornscheuer UT. 2003. Immobilizing enzymes: how to create more suitable biocatalysts. Angew Chem Int Ed Engl. 42(29):3336–3337.
   PubMed Web of Science ®Google Scholar
• Bradford MM. 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.
   PubMed Web of Science ®Google Scholar
• Brenneis R, Baeck B. 2012. Esterification of fatty acids using Candida antarctica lipase A in water-abundant systems. Biotechnol Lett. 34:1459–1463.
   PubMed Web of Science ®Google Scholar
• Cao L. 2005. Immobilised enzymes: science or art? Curr Opin Chem Biol. 9(2):217–226.
   PubMed Web of Science ®Google Scholar
• Cao Q, Zhang Y, Chen W, Meng X, Liu B. 2018. Hydrophobicity and physicochemical properties of agarose film as affected by chitosan addition. Int J Biol Macromol. 106:1307–1313
   PubMed Web of Science ®Google Scholar
• Araújo CE, Pessoa BA, Oliveira U, Matos L, Sabino AW, Monteiro R, dos Santos J, Gonçalves L. 2020. Improving the catalytic features of the lipase from Rhizomucor miehei immobilized on chitosan-based hybrid matrices by altering the chemical activation conditions. Quím. Nova. 43:1234–1239.
   Web of Science ®Google Scholar
• Casas-Godoy L, Duquesne S, Bordes F. 2012. Lipases and phospholipases. Methods Mol Biol. 861:3–30.
   PubMedGoogle Scholar
• Cavalcante FTT, Cavalcante ALG, de Sousa IG, Neto FS, Dos Santos JCS. 2021. Current status and future perspectives of supports and protocols for enzyme immobilization. Catalysts. 11(10):1222.
   Web of Science ®Google Scholar
• Cavalcante ALG, Chaves AV, Fechine P, Holanda Alexandre BA, Freire JYN, Davi TM, Neto DMB, de Sousa FS, da Silva Moreira IG, de Oliveira K, et al. 2022. Chemical modification of clay nanocomposites for the improvement of the catalytic properties of Lipase A from Candida antarctica. Process Biochem. 120:1–14.
   Web of Science ®Google Scholar
• Cavalcante FTT, da Fonseca AM, Alexandre JYNH, dos Santos JC. 2022. A stepwise docking and molecular dynamics approach for enzymatic biolubricant production using Lipase Eversa® Transform as a biocatalyst. Ind Crops Prod. 187:115450.
   Web of Science ®Google Scholar
• Cavalcanti EDC, Aguieiras ÉCG, da Silva PR, Duarte JG, Cipolatti EP, Fernandez-Lafuente R, da Silva JAC, Freire, DMG. 2018. Improved production of biolubricants from soybean oil and different polyols via esterification reaction catalyzed by immobilized lipase from Candida rugosa. Fuel. 215:705–713.
   Web of Science ®Google Scholar
• Cen Y, Singh W, Arkin M, Moody TS, Huang M, Zhou J, Wu Q, Reetz MT. 2019. Artificial cysteine-lipases with high activity and altered catalytic mechanism created by laboratory evolution. Nat. Commun. 10:3198.
   PubMed Web of Science ®Google Scholar
• Chakraborty R, RoyChowdhury D. 2013. Fish bone derived natural hydroxyapatite-supported copper acid catalyst: Taguchi optimization of semibatch oleic acid esterification. Chem Eng J. 215–216:491–499.
   Web of Science ®Google Scholar
• Chandra Dey S, Al-Amin M, Ur Rashid T, Zakir Sultan M, Ashaduzzaman M, Sarker M, Md Shamsuddin S. 2016. PREPARATION, CHARACTERIZATION AND PERFORMANCE EVALUATION OF CHITOSAN AS AN ADSORBENT FOR REMAZOL RED. Int J Latest Res Eng Technol. 2:52–62.
   Google Scholar
• Chandra P, Singh R, Arora, PK, Enespa,. 2020. Microbial lipases and their industrial applications: a comprehensive review. Microb Cell Fact. 19(1):169.
   PubMed Web of Science ®Google Scholar
• Chang MY, Chan ES, Song CP. 2021. Biodiesel production catalysed by low-cost liquid enzyme Eversa® Transform 2.0: effect of free fatty acid content on lipase methanol tolerance and kinetic model. Fuel. 283:119266.
   Web of Science ®Google Scholar
• Chaturvedi SK, Zaidi N, Alam P, Khan JM, Qadeer A, Siddique IA, Asmat S, Zaidi Y, Khan RH. 2015. Unraveling comparative anti-amyloidogenic behavior of pyrazinamide and D-Cycloserine: a mechanistic biophysical insight. PLoS One. 10(8):e0136528.
   PubMed Web of Science ®Google Scholar
• Chenthamarakshan A, Parambayil N, Miziriya N, Soumya PS, Lakshmi MSK, Ramgopal A, Dileep A, Nambisan P. 2017. Optimization of laccase production from Marasmiellus palmivorus LA1 by Taguchi method of Design of experiments. BMC Biotechnol. 17(1):12.
   PubMedGoogle Scholar
• Choi JM, Han SS, Kim HS. 2015. Industrial applications of enzyme biocatalysis: current status and future aspects. Biotechnol Adv. 33(7):1443–1454.
   PubMed Web of Science ®Google Scholar
• da Fonseca AM, de Freitas ÍB, Soares NB, de Araújo FAM, Gaieta EM, Dos Santos JCS, Sobrinho ACN, Marinho ES, Colares RP. 2022. Synthesis, biological activity, and in silico study of bioesters derived from Bixin by the CALB enzyme. Biointerface Res Appl Chem. 12:5901–5917.
   Web of Science ®Google Scholar
• Dantas A, Valério A, Ninow JL, de Oliveira JV, de Oliveira D. 2019. Potential application of Thermomyces lanuginosus lipase (TLL) immobilized on nonporous polystyrene particles. Environ Prog Sustainable Energy. 38(2):608–613.
   Web of Science ®Google Scholar
• Datta S, Christena LR, Rajaram, YRS. 2013. Enzyme immobilization: an overview on techniques and support materials. 3 Biotech. 3(1):1–9.
   PubMedGoogle Scholar
• de Oliveira ALB, Cavalcante FTT, Moreira KS, Monteiro RRC, Rocha TG, Souza JES, da Fonseca AM, Lopes AAS, Guimarães AP, de Lima RKC, et al. 2021. Lipases immobilized onto nanomaterials as biocatalysts in biodiesel production: scientific context, challenges, and opportunities. Rev Virtual Quim. 13(4):875–891.
   Web of Science ®Google Scholar
• de Oliveira UMF, Lima de Matos LJB, de Souza MCM, Pinheiro BB, dos Santos JCS, Gonçalves LRB. 2018. Effect of the presence of surfactants and immobilization conditions on catalysts’ properties of Rhizomucor miehei lipase onto chitosan. Appl Biochem Biotechnol. 184(4):1263–1285.
   PubMed Web of Science ®Google Scholar
• de Queiroz Antonino RSCM, Lia Fook BRP, de Oliveira Lima VA, de Farias Rached RÍ, Lima EPN, da Silva Lima RJ, Peniche Covas CA, Lia Fook MV. 2017. Preparation and characterization of chitosan obtained from shells of shrimp (Litopenaeus vannamei Boone). Mar Drugs. 15(5):141.
   PubMed Web of Science ®Google Scholar
• de Souza TC, de Sousa Fonseca T, de Sousa Silva J, Lima PJM, Neto C, Monteiro RRC, Rocha MVP, de Mattos MC, dos Santos JCS, Gonçalves LRB. 2020. Modulation of lipase B from Candida antarctica properties via covalent immobilization on eco-friendly support for enzymatic kinetic resolution of rac-indanyl acetate. Bioprocess Biosyst Eng. 43(12):2253–2268.
   PubMed Web of Science ®Google Scholar
• Dos Santos JCS, Rueda N, Torres R, Barbosa O, Gonçalves LRB, Fernandez-Lafuente R. 2015. Evaluation of divinylsulfone activated agarose to immobilize lipases and to tune their catalytic properties. Process Biochem. 50(6):918–927.
   Web of Science ®Google Scholar
• Drout RJ, Robison L, Farha OK. 2019. Catalytic applications of enzymes encapsulated in metal–organic frameworks. Coord Chem Rev. 381:151–160.
   Web of Science ®Google Scholar
• Elias N, Wahab RA, Jye LW, Mahat NA, Chandren S, Jamalis J. 2021. Taguchi orthogonal design assisted immobilization of Candida rugosa lipase onto nanocellulose-silica reinforced polyethersulfone membrane: physicochemical characterization and operational stability. Cellulose. 28(9):5669–5691.
   Web of Science ®Google Scholar
• Fernandes KV, Cavalcanti EDC, Cipolatti EP, Aguieiras ECG, Pinto MCC, Tavares FA, da Silva PR, Fernandez-Lafuente R, Arana-Peña S, Pinto JC, et al. 2021. Enzymatic synthesis of biolubricants from by-product of soybean oil processing catalyzed by different biocatalysts of Candida rugosa lipase. Catal Today. 362:122–129.
   Web of Science ®Google Scholar
• Fernandez-Lopez L, Bartolome-Cabrero R, Rodriguez MD, Dos Santos CS, Rueda N, Fernandez-Lafuente R. 2015. Stabilizing effects of cations on lipases depend on the immobilization protocol. RSC Adv. 5(102):83868–83875.
   Web of Science ®Google Scholar
• Ferreira Gonçalves GR, Ramos Gandolfi OR, Brito MJP, Bonomo RCF, da Costa Ilhéu Fontan R, Veloso CM. 2021. Immobilization of porcine pancreatic lipase on activated carbon by adsorption and covalent bonding and its application in the synthesis of butyl butyrate. Process Biochem. 111:114–123.
   Web of Science ®Google Scholar
• Ferreira Mota G, Germano de Sousa I, Luiz Barros de Oliveira A, Luthierre Gama Cavalcante A, da Silva Moreira K, Thálysson Tavares Cavalcante F, Erick da Silva Souza J, Rafael de Aguiar Falcão Í, Guimarães Rocha T, Bussons Rodrigues Valério R, et al. 2022. Biodiesel production from microalgae using lipase-based catalysts: current challenges and prospects. Algal Res. 62:102616.
   Google Scholar
• Filho DG, Silva AG, Guidini CZ. 2019. Lipases: sources, immobilization methods, and industrial applications. Appl Microbiol Biotechnol. 103(18):7399–7423.
   PubMed Web of Science ®Google Scholar
• Fonseca TdS, Vega KB, da Silva MR, de Oliveira MdC, de Lemos TLG, Contente ML, Molinari F, Cespugli M, Fortuna S, Gardossi L, et al. 2020. Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: a case of study and rationalization. Mol. Catal. 485:110819.
   Google Scholar
• Fraga FC, Valério A, de Oliveira VA, Di Luccio M, de Oliveira D. 2019. Effect of magnetic field on the Eversa® Transform 2.0 enzyme: enzymatic activity and structural conformation. Int J Biol Macromol. 122:653–658.
   PubMed Web of Science ®Google Scholar
• Fukui Y, Inamura R, Fujimoto K. 2021. Preparation of agarose xerogel nanoparticles by solvent evaporation from water nanodroplets. Polym J. 53:815–821.
   Web of Science ®Google Scholar
• Ghasemi S, Yousefi M, Nikseresht A, Omidi H. 2021. Covalent binding and in-situ immobilization of lipases on a flexible nanoporous material. Process Biochem. 102:92–101.
   Web of Science ®Google Scholar
• Głąb M, Kudłacik-Kramarczyk S, Drabczyk A, Guigou MD, Sobczak-Kupiec A, Mierzwiński D, Gajda P, Walter J, Tyliszczak B. 2021. Multistep chemical processing of crickets leading to the extraction of chitosan used for synthesis of polymer drug carriers. Materials (Basel). 14(17):5070.
   PubMed Web of Science ®Google Scholar
• Gür SD, İdil N, Aksöz N. 2018. Optimization of enzyme co-immobilization with sodium alginate and glutaraldehyde-activated chitosan beads. Appl Biochem Biotechnol. 184(2):538–552.
   PubMed Web of Science ®Google Scholar
• Halder SK, Maity C, Jana A, Ghosh K, Das A, Paul T, Mohapatra PKD, Pati BR, Mondal KC. 2014. Chitinases biosynthesis by immobilized Aeromonas hydrophila SBK1 by prawn shells valorization and application of enzyme cocktail for fungal protoplast preparation. J Biosci Bioeng. 117(2):170–177. 10.1016/j.jbiosc.2013.07.011. 23994224
   PubMed Web of Science ®Google Scholar
• Halgren TA. 1996. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem. 17(5–6):490–519.
   Web of Science ®Google Scholar
• Hanwell MD, Curtis DE, Lonie DC, Vandermeersch T, Zurek E, Hutchison GR. 2012. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J. Cheminform. 4:17.
   PubMed Web of Science ®Google Scholar
• Heikal EK, Elmelawy MS, Khalil SA, Elbasuny NM. 2017. Manufacturing of environment friendly biolubricants from vegetable oils. Egypt J Pet. 26(1):53–59.
   Google Scholar
• Hu Z, Hong P, Liao M, Kong S, Huang N, Ou C, Li S. 2016. Preparation and characterization of chitosan-agarose composite films. Materials (Basel). 9(10):816.
   PubMed Web of Science ®Google Scholar
• ISmail AR, Kashtoh H, Baek KH. 2021. Temperature-resistant and solvent-tolerant lipases as industrial biocatalysts: biotechnological approaches and applications. Int J Biol Macromol. 187:127–142.
   PubMed Web of Science ®Google Scholar
• Karmakar B, Dhawane SH, Halder G. 2018. Optimization of biodiesel production from castor oil by Taguchi design. J Environ Chem Eng. 6(2):2684–2695.
   Web of Science ®Google Scholar
• Kim H, Choi N, Kim Y, Kim HR, Lee J, Kim IH. 2019. Immobilized lipase-catalyzed esterification for synthesis of trimethylolpropane triester as a biolubricant. Renew. Energy. 130:489–494.
   Web of Science ®Google Scholar
• Kleinaite E, Jaška V, Tvaska B, Matijošyte I. 2014. A cleaner approach for biolubricant production using biodiesel as a starting material. J Clean Prod. 75:40–44.
   Web of Science ®Google Scholar
• Laskowski RA, MacArthur MW, Moss DS, Thornton JM. 1993. PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Crystallogr. 26:283–291.
   Web of Science ®Google Scholar
• Li K, Wang J, He Y, Cui G, Abdulrazaq MA, Yan Y. 2018. Enhancing enzyme activity and enantioselectivity of Burkholderia cepacia lipase via immobilization on melamine-glutaraldehyde dendrimer modified magnetic nanoparticles. Chem Eng J. 351:258–268.
   Web of Science ®Google Scholar
• Lima PJM, da Silva RM, Neto CACG, Gomes E Silva NC, Souza JEDS, Nunes YL, Sousa dos Santos JC. 2021. An overview on the conversion of glycerol to value‐added industrial products via chemical and biochemical routes. Biotechnol Appl Biochem. 2021. https://doi.org/10.1002/bab.2098
   Google Scholar
• Liu S, Bilal M, Rizwan K, Gul I, Rasheed T, Iqbal HMN. 2021. Smart chemistry of enzyme immobilization using various support matrices – a review. Int J Biol Macromol. 190:396–408.
   PubMed Web of Science ®Google Scholar
• Melo ADQ, Silva FFM, Dos Santos JCS, Fernández-Lafuente R, Lemos TLG, Dias Filho FA. 2017. Synthesis of benzyl acetate catalyzed by lipase immobilized in nontoxic chitosan-polyphosphate beads. Molecules. 22(12):2165.
   PubMed Web of Science ®Google Scholar
• Migneault I, Dartiguenave C, Bertrand MJ, Waldron KC. 2004. Glutaraldehyde: behavior in aqueous solution, reaction with proteins, and application to enzyme crosslinking. Biotechniques. 37(5):790–802.
   PubMed Web of Science ®Google Scholar
• Miranda LP, Guimarães JR, Giordano RC, Fernandez-Lafuente R, Tardioli PW. 2020. Composites of crosslinked aggregates of eversa® transform and magnetic nanoparticles. Performance in the ethanolysis of soybean oil. Catalysts. 10(8):817–811.
   Web of Science ®Google Scholar
• Mo H, Qiu J. 2020. Preparation of chitosan/magnetic porous biochar as support for cellulase immobilization by using glutaraldehyde. Polymers (Basel). 12(11):2672–2614.
   PubMed Web of Science ®Google Scholar
• Monteiro RRC, Arana-Peña S, da Rocha TN, Miranda LP, Berenguer-Murcia Á, Tardioli PW, dos Santos JCS, Fernandez-Lafuente R. 2021a. Liquid lipase preparations designed for industrial production of biodiesel. Is it really an optimal solution? Renew Energy. 164:1566–1587.
   Web of Science ®Google Scholar
• Monteiro RRC, Lima PJM, Pinheiro BB, Freire TM, Dutra LMU, Fechine PBA, Gonçalves LRB, de Souza MCM, dos Santos JCS, Fernandez-Lafuente R. 2019a. Immobilization of lipase A from Candida antarctica onto chitosan-coated magnetic nanoparticles. IJMS. 20(16):4018.
   Google Scholar
• Monteiro RRC, Neto DMA, Fechine PBA, Lopes AAS, Gonçalves LRB, dos Santos JCS, de Souza MCM, Fernandez-Lafuente R. 2019b. Ethyl butyrate synthesis catalyzed by lipases A and B from Candida antarctica immobilized onto magnetic nanoparticles. Improvement of biocatalysts’ performance under ultrasonic irradiation. IJMS. 20(22):5807.
   Google Scholar
• Monteiro RRC, Oliveira ALB, Menezes FL, Souza MCM, Fechine PBA, DOS Santos JCS. 2022. Improvement of enzymatic activity and stability of lipase A from Candida antartica onto halloysite nanotubes with Taguchi method for optimized immobilization. Appl Clay Sci. 228:106634.
   Web of Science ®Google Scholar
• Monteiro RRC, Virgen-Ortiz JJ, Berenguer-Murcia Á, da Rocha TN, dos Santos JCS, Alcántara AR, Fernandez-Lafuente R. 2021b. Biotechnological relevance of the lipase A from Candida antarctica. Catal Today. 362:141–154.
   Web of Science ®Google Scholar
• Moreira KDS, Barros de Oliveira AL, Saraiva de Moura Júnior L, Germano de Sousa I, Luthierre Gama Cavalcante A, Simão Neto F, Bussons Rodrigues Valério R, Valério Chaves A, de Sousa Fonseca T, Cruz DMV, et al. 2022. Taguchi design-assisted co-immobilization of Lipase A and B from Candida antarctica onto Chitosan: characterization, kinetic resolution application, and docking studies. Chem Eng Res Des. 177:223–244.
   Web of Science ®Google Scholar
• Moreira KDS, de Oliveira ALB, Júnior LSDM, Monteiro RRC, da Rocha TN, Menezes FL, Fechine L, Denardin JC, Michea S, Freire RM, et al. 2020. Lipase from Rhizomucor miehei immobilized on magnetic nanoparticles: performance in Fatty Acid Ethyl Ester (FAEE) optimized production by the Taguchi method. Front Bioeng Biotechnol. 8:693.
   PubMedGoogle Scholar
• Morris GM, Ruth H, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ. 2009. Software news and updates AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem. 30(16):2785–2791.
   PubMed Web of Science ®Google Scholar
• Mortazavi S, Aghaei H. 2020. Make proper surfaces for immobilization of enzymes: immobilization of lipase and α-amylase on modified Na-sepiolite. Int J Biol Macromol. 164:1–12.
   PubMed Web of Science ®Google Scholar
• Nazor J, Liu J, Huisman G. 2021. Enzyme evolution for industrial biocatalytic cascades. Curr Opin Biotechnol. 69:182–190.
   PubMed Web of Science ®Google Scholar
• Nery EW, Kubota LT. 2016. Evaluation of enzyme immobilization methods for paper-based devices-a glucose oxidase study. J Pharm Biomed Anal. 117:551–559.
   PubMed Web of Science ®Google Scholar
• Nouri M, Khodaiyan F. 2020. Green synthesis of chitosan magnetic nanoparticles and their application with poly-aldehyde kefiran cross-linker to immobilize pectinase enzyme. Biocatal. Agric. Biotechnol. 29:101681.
   Web of Science ®Google Scholar
• Nunes YL, de Menezes FL, de Sousa IG, Cavalcante ALG, Cavalcante FTT, da Silva Moreira K, de Oliveira ALB, Mota GF, da Silva Souza JE, de Aguiar Falcão IR, et al. 2021. Chemical and physical Chitosan modification for designing enzymatic industrial biocatalysts: how to choose the best strategy? Int J Biol Macromol. 181:1124–1170.
   PubMed Web of Science ®Google Scholar
• Nwagu TN, Okolo B, Aoyagi H. 2021. Immobilization of raw starch saccharifying amylase on glutaraldehyde activated chitin flakes increases the enzyme operation range. Bioresour Technol. Reports. 13:100645.
   Google Scholar
• Okura NS, Sabi GJ, Crivellenti MC, Gomes RAB, Fernandez-Lafuente R, Mendes AA. 2020. Improved immobilization of lipase from Thermomyces lanuginosus on a new chitosan-based heterofunctional support: mixed ion exchange plus hydrophobic interactions. Int J Biol Macromol. 163:550–561.
   PubMed Web of Science ®Google Scholar
• Pal G, Araújo LS, Vidal MS, Baldani JI, Henrique C, Gadelha S. 2014. Modelagem molecular de proteínas: o caso de uma glucoronosiltransferase (GumK) de Gluconacetobacter diazotrophicus PAL5. J Biol Pharm Agric Manag. 10:1–6.
   Google Scholar
• Pandey D, Daverey A, Arunachalam K. 2020. Biochar: production, properties and emerging role as a support for enzyme immobilization. J Clean Prod. 255:120267.
   Web of Science ®Google Scholar
• Paroul N, Grzegozeski LP, Chiaradia V, Treichel H, Cansian RL, Oliveira JV, De Oliveira D. 2011. Solvent-free geranyl oleate production by enzymatic esterification. Bioprocess Biosyst Eng. 34:323–329.
   PubMed Web of Science ®Google Scholar
• Parsa P, Paydayesh A, Davachi SM. 2019. Investigating the effect of tetracycline addition on nanocomposite hydrogels based on polyvinyl alcohol and chitosan nanoparticles for specific medical applications. Int J Biol Macromol. 121:1061–1069.
   PubMed Web of Science ®Google Scholar
• Pawlak A, Mucha M. 2003. Thermogravimetric and FTIR studies of chitosan blends. Thermochim Acta. 396(1–2):153–166.
   Web of Science ®Google Scholar
• Pettersen EF, Goddard TD, Huang CC, Meng EC, Couch GS, Croll TI, Morris JH, Ferrin TE. 2021. UCSF ChimeraX: structure visualization for researchers, educators, and developers. Protein Sci. 30(1):70–82.
   PubMed Web of Science ®Google Scholar
• Pinheiro BB, Rios NS, Rodríguez Aguado E, Fernandez-Lafuente R, Freire TM, Fechine PBA, dos Santos JCS, Gonçalves LRB. 2019. Chitosan activated with divinyl sulfone: a new heterofunctional support for enzyme immobilization. Application in the immobilization of lipase B from Candida antarctica. Int J Biol Macromol. 130:798–809.
   PubMed Web of Science ®Google Scholar
• Pourmadadi M, Ahmadi M, Abdouss M, Yazdian F, Rashedi H, Navaei-Nigjeh M, Hesari Y. 2022. The synthesis and characterization of double nanoemulsion for targeted co-delivery of 5-fluorouracil and curcumin using pH-sensitive agarose/chitosan nanocarrier. J. Drug Deliv. Sci. Technol. 70:102849.
   Google Scholar
• Ramachandran GN, Ramakrishnan C, Sasisekharan V. 1963. Stereochemistry of Polypeptide Chain Conformations. J Mol Biol. 7(1):95–99.
   PubMed Web of Science ®Google Scholar
• Reis CLB, de Sousa EYA, de França Serpa J, Oliveira RC, Dos Santos, JCS. 2019. Design of immobilized enzyme biocatalysts: drawbacks and opportunities. Quim Nova. 42:768–783.
   Web of Science ®Google Scholar
• Ribeiro ES, de Farias BS, Sant’Anna Cadaval Junior TR, de Almeida Pinto LA, Diaz PS. 2021. Chitosan–based nanofibers for enzyme immobilization. Int J Biol Macromol. 183:1959–1970.
   PubMed Web of Science ®Google Scholar
• Rios NS, Morais EG, dos Santos Galvão W, Andrade Neto DM, dos Santos JCS, Bohn F, Correa MA, Fechine PBA, Fernandez-Lafuente R, Gonçalves, LRB. 2019. Further stabilization of lipase from Pseudomonas fluorescens immobilized on octyl coated nanoparticles via chemical modification with bifunctional agents. Int J Biol Macromol. 141:313–324.
   PubMed Web of Science ®Google Scholar
• Rios NS, Pinheiro MP, dos Santos JCS, de S. Fonseca T, Lima LD, de Mattos MC, Freire DMG, da Silva IJ, Rodríguez-Aguado E, Gonçalves LRB. 2016. Strategies of covalent immobilization of a recombinant Candida antarctica lipase B on pore-expanded SBA-15 and its application in the kinetic resolution of (R,S)-Phenylethyl acetate. J Mol Catal B Enzym. 133:246–258.
   Google Scholar
• Rocha TG, Pedro PH, de Souza MCM, Monteiro RRC, dos Santos JCS. 2021. Lipase cocktail for optimized biodiesel production of free fatty acids from residual chicken oil. Catal Lett. 151:1155–1166.
   Web of Science ®Google Scholar
• Rodrigues RC, Virgen-Ortíz JJ, dos Santos JCS, Berenguer-Murcia Á, Alcantara AR, Barbosa O, Ortiz C, Fernandez-Lafuente R. 2019. Immobilization of lipases on hydrophobic supports: immobilization mechanism, advantages, problems, and solutions. Biotechnol Adv. 37(5):746–770.
   PubMed Web of Science ®Google Scholar
• Saeedi Garakani S, Khanmohammadi M, Atoufi Z, Kamrava SK, Setayeshmehr M, Alizadeh R, Faghihi F, Bagher Z, Davachi SM, Abbaspourrad A. 2020. Fabrication of chitosan/agarose scaffolds containing extracellular matrix for tissue engineering applications. Int J Biol Macromol. 143:533–545.
   PubMed Web of Science ®Google Scholar
• Sahin S, Ozmen I. 2020. Covalent immobilization of trypsin on polyvinyl alcohol-coated magnetic nanoparticles activated with glutaraldehyde. J Pharm Biomed Anal. 184:113195.
   PubMed Web of Science ®Google Scholar
• Sankar S, Ponnuraj K. 2020. Less explored plant lipases: modeling and molecular dynamics simulations of plant lipases in different solvents and temperatures to understand structure-function relationship. Int J Biol Macromol. 164:3546–3558.
   PubMed Web of Science ®Google Scholar
• Schlepütz M, Buthe A, Brenneis R, Ansorge-Schumacher MB. 2008. Lipase-catalysed synthesis of ester oils from biodiesel by-products. Biocatal Biotransformation. 26:220–227.
   Web of Science ®Google Scholar
• Sheldon RA, Brady D. 2021. Streamlining design, engineering, and applications of enzymes for sustainable biocatalysis. ACS Sustainable Chem Eng. 9(24):8032–8052.
   Web of Science ®Google Scholar
• Sheldon RA, van Pelt S. 2013. Enzyme immobilisation in biocatalysis: why, what and how. Chem Soc Rev. 42(15):6223–6235.
   PubMed Web of Science ®Google Scholar
• Silva ARM, Alexandre JYNH, Souza JES, Neto JGL, Junior PGDS, Rocha MVP, DOS Santos JC. 2022. The chemistry and applications of Metal-Organic Frameworks (MOFs) as industrial enzyme immobilization systems. Molecules. 27(14):4529.
   PubMed Web of Science ®Google Scholar
• Singh R, Bhattacharya B, Tomar SK, Singh V, Singh PK. 2017. Electrical, optical and electrophotochemical studies on agarose based biopolymer electrolyte towards dye sensitized solar cell application. Meas J Int Meas Confed. 102:214–219.
   Web of Science ®Google Scholar
• Sousa EYA, da Silva Souza JE, de Castro Monteiro RR, de Oliveira ALB, dos Santos JCS, da Fonseca AM. 2021. Preparation, characterization, and enantioselectivity of polyacrylate microcapsules entrapping Ananas comosus. Extract Rev Virtual Quim. 13:1319–1329.
   Web of Science ®Google Scholar
• Souza JES, Monteiro RRC, Rocha TG, Moreira KS, Cavalcante FTT, de Sousa Braz AK, de Souza MCM, dos Santos, JCS. 2020. Sonohydrolysis using an enzymatic cocktail in the preparation of free fatty acid. 3 Biotech. 10(6):254–264.
   PubMedGoogle Scholar
• Souza JEDS, Oliveira GD, Alexandre J, Neto JGL, Sales MB, Junior PDS, Oliveira AD, Souza Md, Santos JD. 2022. A comprehensive review on the use of Metal–Organic Frameworks (MOFs) coupled with enzymes as biosensors. Electrochem. 3(1):89–113.
   Google Scholar
• Sun S, Guo J, Chen X. 2021. Biodiesel preparation from Semen Abutili (Abutilon theophrasti Medic.) seed oil using low-cost liquid lipase Eversa® transform 2.0 as a catalyst. Ind Crops Prod. 169:113643.
   Web of Science ®Google Scholar
• Sung HW, Chang Y, Liang IL, Chang WH, Chen YC. 2000. Fixation of biological tissues with a naturally occurring crosslinking agent: fixation rate and effects of pH, temperature, and initial fixative concentration. J Biomed Mater Res. 52(1):77–87. :1 < 77::AID-JBM10 > 3.0.CO;2-6.
   PubMed Web of Science ®Google Scholar
• Taha M, Ismail NH, Khan A, Shah SAA, Anwar A, Halim SA, Fatmi MQ, Imran S, Rahim F, Khan KM. 2015. Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies. Bioorg Med Chem Lett. 25(16):3285–3289.
   PubMed Web of Science ®Google Scholar
• Tam B, Sinha S, Wang SM. 2020. Combining Ramachandran plot and molecular dynamics simulation for structural-based variant classification: using TP53 variants as model. Comput Struct Biotechnol J. 18:4033–4039.
   PubMed Web of Science ®Google Scholar
• Taslimi P, Erden Y, Mamedov S, Zeynalova L, Ladokhina N, Tas R, Tuzun B, Sujayev A, Sadeghian N, Alwasel SH, et al. 2021. The biological activities, molecular docking studies, and anticancer effects of 1-arylsuphonylpyrazole derivatives. J Biomol Struct Dyn. 39(9):3336–3346.
   PubMed Web of Science ®Google Scholar
• Tian W, Chen C, Lei X, Zhao J, Liang J. 2018. CASTp 3.0: computed atlas of surface topography of proteins. Nucleic Acids Res. 46(W1):W363–W367.
   PubMed Web of Science ®Google Scholar
• Trivedi TJ, Kumar A. 2014. Efficient extraction of agarose from red algae using ionic liquids. GSC. 04(04):190–201.
   Google Scholar
• Trott O, Olson AJ. 2009. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem. 31(2):455–461.
   Web of Science ®Google Scholar
• Ugwuodo CJ, Nwagu TN. 2020. Stabilizing enzymes by immobilization on bacterial spores: a review of literature. Int J Biol Macromol. 166:238–250.
   PubMed Web of Science ®Google Scholar
• Unugul T, Kutluk T, Gürkaya Kutluk B, Kapucu N. 2020. Environmentally friendly processes from coffee wastes to trimethylolpropane esters to be considered biolubricants. J Air Waste Manag Assoc. 70(11):1198–1215.
   PubMedGoogle Scholar
• Urrutia P, Bernal C, Wilson L, Illanes A. 2018. Use of chitosan heterofunctionality for enzyme immobilization: β-galactosidase immobilization for galacto-oligosaccharide synthesis. Int J Biol Macromol. 116:182–193.
   PubMed Web of Science ®Google Scholar
• Vahidi M, Imanparast S, Jahandar H, Forootanfar H, Mojtabavi S, Faramarzi MA. 2021. An organic solvent-tolerant lipase of Streptomyces pratensis MV1 with the potential application for enzymatic improvement of n6/n3 ratio in polyunsaturated fatty acids from fenugreek seed oil. J Food Sci Technol. 58(7):2761–2772.
   PubMed Web of Science ®Google Scholar
• Valério RBR, Cavalcante ALG, Mota GF, de Sousa IG, da Silva Souza JE, Cavalcante FTT, Moreira K, da Silva Moreira S, de Aguiar Falcão IR, et al. 2022. Understanding the biocatalytic potential of lipase from Rhizopus chinensis. Biointerface Res Appl Chem. 12:4230–4260.
   Web of Science ®Google Scholar
• Varma R, Vasudevan S. 2020. Extraction, characterization, and antimicrobial activity of chitosan from horse mussel Modiolus modiolus. ACS Omega. 5(32):20224–20230.
   PubMed Web of Science ®Google Scholar
• Velasco-Lozano S, Rocha-Martin J, Dos Santos, JCS. 2022. Editorial: designing carrier-free immobilized enzymes for biocatalysis. Front Bioeng Biotechnol. 10:924743–924745.
   PubMed Web of Science ®Google Scholar
• Verma ML, Kumar S, Das A, Randhawa JS, Chamundeeswari M. 2020. Chitin and chitosan-based support materials for enzyme immobilization and biotechnological applications. Environ Chem Lett. 18:315–323.
   Web of Science ®Google Scholar
• Vilas Bôas RN, Lima RD, Mendes AA, Freitas L, Bento HBS, Carvalho AKFD, de Castro HF. 2021. Batch and continuous production of biolubricant from fusel oil and oleic acid: lipase screening, reactor system development, and reaction optimization. Chem Eng Process Process Intensif. 168:108568.
   Web of Science ®Google Scholar
• Villeneuve P, Muderhwa JM, Graille J, Haas MJ. 2000. Customizing lipases for biocatalysis: a survey of chemical, physical and molecular biological approaches. J Mol Catal B Enzym. 9(4–6):113–148.
   Google Scholar
• Virgen-Ortíz JJ, dos Santos JCS, Ortiz C, Berenguer-Murcia Á, Barbosa O, Rodrigues RC, Fernandez-Lafuente R. 2019. Lecitase ultra: a phospholipase with great potential in biocatalysis. Mol. Catal. 473:110405.
   Google Scholar
• Virgen-Ortíz JJ, Pedrero SG, Fernandez-Lopez L, Lopez-Carrobles N, Gorines BC, Otero C, Fernandez-Lafuente R. 2017. Desorption of lipases immobilized on octyl-agarose beads and coated with ionic polymers after thermal inactivation. Stronger adsorption of polymers/unfolded protein composites. Molecules. 22(1):91.
   PubMed Web of Science ®Google Scholar
• Wahab RA, Elias N, Abdullah F, Ghoshal SK. 2020. On the taught new tricks of enzymes immobilization: an all-inclusive overview. React Funct Polym. 152:104613.
   Web of Science ®Google Scholar
• Wang Y, Zhang X, Han N, Wu Y, Wei D. 2018. Oriented covalent immobilization of recombinant protein A on the glutaraldehyde activated agarose support. Int J Biol Macromol. 120(Pt A):100–108.
   PubMedGoogle Scholar
• Webb B, Sali A. 2016. Comparative protein structure modeling using MODELLER. Curr. Protoc. Bioinforma. 54:5.6.1–5.6.37.
   PubMedGoogle Scholar
• Wu L, Qin L, Nie Y, Xu Y, Zhao YL. 2022. Computer-aided understanding and engineering of enzymatic selectivity. Biotechnol Adv. 54:107793.
   PubMed Web of Science ®Google Scholar
• Wu X, Yang C, Ge J. 2017. Green synthesis of enzyme/metal-organic framework composites with high stability in protein denaturing solvents. Bioresour Bioprocess. 4(1):0–7.
   Google Scholar
• Xie J, Zhang Y, Simpson B. 2022. Food enzymes immobilization: novel carriers, techniques and applications. Curr Opin Food Sci. 43:27–35.
   Web of Science ®Google Scholar
• Zaak H, Fernandez-Lopez L, Otero C, Sassi M, Fernandez-Lafuente R. 2017. Improved stability of immobilized lipases via modification with polyethylenimine and glutaraldehyde. Enzyme Microb Technol. 106:67–74.
   PubMed Web of Science ®Google Scholar
• Zdarta J, Meyer AS, Jesionowski T, Pinelo M. 2018. A general overview of support materials for enzyme immobilization: characteristics, properties, practical utility. Catalysts. 8(2):92.
   Web of Science ®Google Scholar
• Zhang DH, Yuwen LX, Peng LJ. 2013. Parameters affecting the performance of immobilized enzyme. J Chem. 2013:1–7.
   Web of Science ®Google Scholar
• Zucca P, Fernandez-Lafuente R, Sanjust E. 2016. Agarose and its derivatives as supports for enzyme immobilization. Molecules. 21(11):1577–1525.
   PubMed Web of Science ®Google Scholar