Zinc hydroxide salts as new supports for the immobilization of Pseudomonas cepacia lipase

References

• Al-Duri B, Yong YP. 1997. Characterisation of the equilibrium behaviour of lipase PS (from Pseudomonas) and lipolase 100L (from Humicola) onto Accurel EP100. J Mol Catal B: enzym. 3(1-4):177–188. doi: 10.1016/S1381-1177(96)00052-5.
   Google Scholar
• Alnoch RC, Martini VP, Glogauer A, Costa ACDS, Piovan L, Muller-Santos M, De Souza EM, Pedrosa FDO, Mitchell DA, Krieger N. 2015. Immobilization and characterization of a new regioselective and enantioselective lipase obtained from a metagenomic library. PLOS One. 10(2):e0114945. doi: 10.1371/journal.pone.0114945.
   PubMed Web of Science ®Google Scholar
• Arizaga GGC, Satyanarayana KG, Wypych F. 2007. Layered hydroxide salts: synthesis, properties and potential applications. Solid State Ion. 178(15–18):1143–1162. doi: 10.1016/j.ssi.2007.04.016.
   Web of Science ®Google Scholar
• Basso A, Serban S. 2019. Industrial applications of immobilized enzymes—A review. J Mol Catal. 479:110607. doi: 10.1016/j.mcat.2019.110607.
   Google Scholar
• Bolivar JM, Woodley JM, Fernandez-Lafuente R. 2022. Is enzyme immobilization a mature discipline? Some critical considerations to capitalize on the benefits of immobilization. Chem Soc Rev. 51(15):6251–6290. doi: 10.1039/D2CS00083K.
   PubMed Web of Science ®Google Scholar
• Chen CS, Fujimoto Y, Girdaukas G, Sih CJ. 1982. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc. 104(25):7294–7299. doi: 10.1021/ja00389a064.
   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. doi: 10.1007/s13205-012-0071-7.
   PubMedGoogle Scholar
• Dhake KP, Deshmukh KM, Wagh YS, Singhal RS, Bhanage BM. 2012. Investigation of steapsin lipase for kinetic resolution of secondary alcohols and synthesis of valuable acetates in non-aqueous reaction medium. J Mol Catal B: Enzym. 77:15–23. doi: 10.1016/j.molcatb.2012.01.009.
   Google Scholar
• Dias GS, Bandeira PT, Jaerger S, Piovan L, Mitchell DA, Wypych F, Krieger N. 2019. Immobilization of Pseudomonas cepacia lipase on layered double hydroxide of Zn/Al-Cl for kinetic resolution of rac-1-phenylethanol. Enzyme Microb Technol. 130:109365. doi: 10.1016/j.enzmictec.2019.109365.
   PubMed Web of Science ®Google Scholar
• Dias M, de Pauloveloso A, do Amaral L, Betim R, Nascimento M, Pilissão C. 2018. Immobilization of Burkholderia cepacia on pristine or functionalized multi‑walled carbon nanotubes and application on enzymatic resolution of (RS)‑1‑Phenylethanol. J Braz Chem Soc. 29:1876–1884. doi: 10.21577/0103-5053.20180063.
   Web of Science ®Google Scholar
• Dong L, Ge C, Qin P, Chen Y, Xu Q. 2014. Immobilization and catalytic properties of candida lipolytic lipase on surface of organic intercalated and modified MgAl-LDHs. Solid State Sci. 31:8–15. doi: 10.1016/j.solidstatesciences.2014.02.006.
   Web of Science ®Google Scholar
• do Amaral LFM, Pilissão C, Krieger N, Wypych F. 2023. Pseudomonas cepacia lipase immobilized on Zn2Al layered double hydroxides: evaluation of different methods of immobilization for the kinetic resolution of (R,S)-1-phenylethanol. Biocatal Biotransfor. :1–15. doi: 10.1080/10242422.2023.2181047.
   Web of Science ®Google Scholar
• da Rocha MG, Nakagaki S, Ucoski GM, Wypych F, Sippel Machado G. 2019. Comparison between catalytic activities of two zinc layered hydroxide salts in brilliant green organic dye bleaching. J Colloid Interface Sci. 541:425–433. doi: 10.1016/j.jcis.2019.01.111.
   PubMed Web of Science ®Google Scholar
• da Silva MLN, Marangoni R, Cursino A, CT, Schreiner WH, Wypych F. 2012. Colorful and transparent poly(vinyl alcohol) composite films filled with layered zinc hydroxide salts, intercalated with anionic orange azo dyes (methyl orange and orange II). Mater Chem Phys. 134(1):392–398. doi: 10.1016/j.matchemphys.2012.03.007.
   Web of Science ®Google Scholar
• Dulęba J, Siódmiak T, Marszałł MP. 2022. The influence of substrate systems on the enantioselective and lipolytic activity of immobilized Amano PS from Burkholderia cepacia lipase (APS-BCL). Process Biochem. 120:126–137. doi: 10.1016/j.procbio.2022.06.003.
   Web of Science ®Google Scholar
• Dwivedee BP, Bhaumik J, Rai SK, Laha JK, Banerjee UC. 2017. Development of nanobiocatalysts through the immobilization of Pseudomonas fluorescens lipase for applications in efficient kinetic resolution of racemic compounds. Bioresour Technol. 239:464–471. doi: 10.1016/j.biortech.2017.05.050.
   PubMed Web of Science ®Google Scholar
• Dwivedee BP, Soni S, Bhimpuria R, Laha JK, Banerjee UC. 2019. Tailoring a robust and recyclable nanobiocatalyst by immobilization of Pseudomonas fluorescens lipase on carbon nanofiber and its application in synthesis of enantiopure carboetomidate analogue. Int J Biol Macromol. 133:1299–1310. doi: 10.1016/j.ijbiomac.2019.03.231.
   PubMed Web of Science ®Google Scholar
• Fernandez-Lafuente R, Armisén P, Sabuquillo P, Fernández-Lorente G, M. Guisán J. 1998. Immobilization of lipases by selective adsorption on hydrophobic supports. Chem Phys Lipids. 93(1–2):185–197. doi: 10.1016/S0009-3084(98)00042-5.
   PubMed Web of Science ®Google Scholar
• Forano C, Vial S, Mousty C. 2006. Nanohybrid enzymes - layered double hydroxides: potential applications. CNANO. 2(3):283–294. doi: 10.2174/1573413710602030283.
   Google Scholar
• Habulin M, Knez Ž. 2009. Optimization of (R,S)-1-phenylethanol kinetic resolution over Candida antarctica lipase B in ionic liquids. J Mol Catal B: enzym. 58(1-4):24–28. doi: 10.1016/j.molcatb.2008.10.007.
   Web of Science ®Google Scholar
• Hasan F, Shah AA, Hameed A. 2006. Industrial applications of microbial lipases. Enzyme Microb Technol. 39(2):235–251. doi: 10.1016/j.enzmictec.2005.10.016.
   Web of Science ®Google Scholar
• Jaerger S, Zimmermann A, Zawadzki SF, Wypych F, Amico SC. 2014. Zinc layered hydroxide salts: intercalation and incorporation into low-density polyethylene. Polímeros. 24(6):673–682. doi: 10.1590/0104-1428.1733.
   Google Scholar
• Joseph B, Ramteke PW, Thomas G. 2008. Cold active microbial lipases: some hot issues and recent developments. Biotechnol Adv. 26(5):457–470. doi: 10.1016/j.biotechadv.2008.05.003.
   PubMed Web of Science ®Google Scholar
• Kisukuri CM, Macedo A, Oliveira CCS, Camargo PHC, Andrade LH. 2013. Investigating the influence of the nterface in thiol-functionalized silver–gold nanoshells over lipase activity. Langmuir. 29(51):15974–15980. doi: 10.1021/la404081n.
   PubMed Web of Science ®Google Scholar
• Klibanov AM. 1997. Why are enzymes less active in organic solvents than in water? Trends Biotechnol. 15(3):97–101. doi: 10.1016/S0167-7799(97)01013-5.
   PubMed Web of Science ®Google Scholar
• Krieger N, Bhatnagar T, Baratti JC, Baron AM, De Lima VM, Mitchell D. 2004. Non-aqueous biocatalysis in heterogeneous solvent systems. Food Technol Biotechnol. 42(4):279–286.
   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. J Chem Eng. 351:258–268. doi: 10.1016/j.cej.2018.06.086.
   Google Scholar
• Lowry RR, Tinsley IJ. 1976. Rapid colorimetric determination of free fatty acids. J Am Oil Chem Soc. 53(7):470–472. doi: 10.1007/BF02636814.
   PubMed Web of Science ®Google Scholar
• Machado GS, Arízaga GGC, Wypych F, Nakagaki S. 2010. Immobilization of anionic metalloporphyrins on zinc hydroxide nitrate and study of an unusual catalytic activity. J Catal. 274(2):130–141. doi: 10.1016/j.jcat.2010.06.012.
   Web of Science ®Google Scholar
• Machado GS, Wypych F, Nakagaki S. 2012. Anionic iron(III) porphyrins immobilized on zinc hydroxide chloride as catalysts for heterogeneous oxidation reactions. Appl Catal, A. 413–414:94–102. doi: 10.1016/j.apcata.2011.10.046.
   Web of Science ®Google Scholar
• Majoni S, Su S, Hossenlopp JM. 2010. The effect of boron-containing layered hydroxy salt (LHS) on the thermal stability and degradation kinetics of poly (methyl methacrylate). Polym Degrad Stab. 95(9):1593–1604. doi: 10.1016/j.polymdegradstab.2010.05.033.
   Web of Science ®Google Scholar
• Manoel EA, dos Santos JCS, Freire DMG, Rueda N, Fernandez-Lafuente R. 2015. Immobilization of lipases on hydrophobic supports involves the open form of the enzyme. Enzyme Microb Technol. 71:53–57. doi: 10.1016/j.enzmictec.2015.02.001.
   PubMed Web of Science ®Google Scholar
• Marangoni R, Ramos LP, Wypych F. 2009. New multifunctional materials obtained by the intercalation of anionic dyes into layered zinc hydroxide nitrate followed by dispersion into poly(vinyl alcohol) (PVA). J Colloid Interface Sci. 330(2):303–309. doi: 10.1016/j.jcis.2008.10.081.
   PubMed Web of Science ®Google Scholar
• Mateo C, Palomo JM, Fernandez-Lorente G, Guisan JM, Fernandez-Lafuente R. 2007. Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb Technol. 40(6):1451–1463. doi: 10.1016/j.enzmictec.2007.01.018.
   Web of Science ®Google Scholar
• Nguyen LA, He H, Pham-Huy C. 2006. Chiral drugs: an overview. Int J Biomed Sci. 2(2):85–100.
   PubMedGoogle Scholar
• Ortiz C, Ferreira ML, Barbosa O, dos Santos JCS, Rodrigues RC, Berenguer-Murcia Á, Briand LE, Fernandez-Lafuente R. 2019. Novozym 435: the “perfect” lipase immobilized biocatalyst? Catal Sci Technol. 9(10):2380–2420. doi: 10.1039/C9CY00415G.
   Web of Science ®Google Scholar
• Persson M, Mladenoska I, Wehtje E, Adlercreutz P. 2002. Preparation of lipases for use in organic solvents. Enzyme Microb Technol. 31(6):833–841. doi: 10.1016/S0141-0229(02)00184-9.
   Web of Science ®Google Scholar
• Pinheiro BB, Rios NS, Rodríguez Aguado E, Fernandez-Lafuente R, Freire TM, Fechine P, BA, dos Santos JCS, Gonçalves L, R, B. 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. doi: 10.1016/j.ijbiomac.2019.02.145.
   PubMed Web of Science ®Google Scholar
• Santos J, dos CS, Barbosa O, Ortiz C, Berenguer-Murcia A, Rodrigues RC, Fernandez-Lafuente R. 2015. Importance of the support properties for immobilization or purification of enzymes. ChemCatChem. 7(16):2413–2432. doi: 10.1002/cctc.201500310.
   Web of Science ®Google Scholar
• Santos LA, dos Alnoch RC, Soares GA, Mitchell DA, Krieger N. 2022. Immobilization of Pseudomonas fluorescens lipase on chitosan crosslinked with polyaldehyde starch for kinetic resolution of sec-alcohols. Process Biochem. 122:238–247. doi: 10.1016/j.procbio.2022.10.014.
   Web of Science ®Google Scholar
• Smith PK, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ, Klenk DC. 1985. Measurement of protein using bicinchoninic acid. Anal Biochem. 150(1):76–85. doi: 10.1016/0003-2697(85)90442-7.
   PubMed Web of Science ®Google Scholar
• Soares D, Serres JDDS, Corazza ML, Mitchell DA, Gonçalves AG, Krieger N. 2015. Analysis of multiphasic behavior during the ethyl esterification of fatty acids catalyzed by a fermented solid with lipolytic activity in a packed-bed bioreactor in a closed-loop batch system. Fuel. 159:364–372. doi: 10.1016/j.fuel.2015.06.087.
   Web of Science ®Google Scholar
• Taviot-Guého C, Prévot V, Forano C, Renaudin G, Mousty C, Leroux F. 2018. Tailoring hybrid layered double hydroxides for the development of innovative applications. Adv Funct Materials. 28(27):1703868. doi: 10.1002/adfm.201703868.
   Web of Science ®Google Scholar
• Tiss A, Carrière F, Verger R. 2001. Effects of gum Arabic on lipase interfacial binding and activity. Anal Biochem. 294(1):36–43. doi: 10.1006/abio.2001.5095.
   PubMed Web of Science ®Google Scholar
• Velazquez-Carriles C, Macias-Rodríguez ME, Carbajal-Arizaga GG, Silva-Jara J, Angulo C, Reyes-Becerril M. 2018. Immobilizing yeast β-glucan on zinc-layered hydroxide nanoparticle improves innate immune response in fish leukocytes. Fish Shellfish Immunol. 82:504–513. doi: 10.1016/j.fsi.2018.08.055.
   PubMed Web of Science ®Google Scholar
• Wang M, Bao W-J, Wang J, Wang K, Xu J-J, Chen H-Y, Xia X-H. 2014. A green approach to the synthesis of novel “Desert rose stone”-like nanobiocatalytic system with excellent enzyme activity and stability. Sci Rep. 4(1):6606. doi: 10.1038/srep06606.
   PubMedGoogle Scholar
• Zheng M, Xiang X, Wang S, Shi J, Deng Q, Huang F, Cong R. 2017. Lipase immobilized in ordered mesoporous silica: a powerful biocatalyst for ultrafast kinetic resolution of racemic secondary alcohols. Process Biochem. 53:102–108. doi: 10.1016/j.procbio.2016.12.005.
   Web of Science ®Google Scholar