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Immobilization of Lipozyme TL 100L for methyl esterification of soybean oil deodorizer distillate

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Abstract

An immobilization method for binding cross-linked enzyme aggregates of Lipozyme TL 100L on macroporous resin NKA (CLEA-TLL@NKA) was developed in this study. The esterification activity of CLEA-TLL@NKA reached 6.4 U/mg. The surface structure of immobilized lipase was characterized by scanning electron microscopy. Methyl esterification reaction of soybean oil deodorizer distillate (SODD) was catalyzed by CLEA-TLL@NKA, which the conversion rate reached 98% and its activity retained over 90% after 20 batches of reaction. Compared with the commercial enzyme Lipozyme TLIM, half-life (t1/2) of CLEA-TLL@NKA increased by 25 times and the catalytic activity increased by approximate 10 times. Thus, CLEA-TLL@NKA had high catalytic activity, good operational stability, and potential industrial application in the field of oil processing.

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References

  • Adlercreutz P (2013) Immobilisation and application of lipases in organic media. Chem Soc Rev 42:6406–6436

    CAS  PubMed  Google Scholar 

  • Bashir F, Asgher M, Hussain F, Randhawa MA (2018) Development and characterization of cross-linked enzyme aggregates of thermotolerant alkaline protease from Bacillus licheniformis. Int J Biol Macromol 113:944–951

    CAS  PubMed  Google Scholar 

  • Brusamarelo CZ, Rosset E, Treichel H, De OD, Mazutti MA, Di LM, Oliveira JV (2010) Kinetics of lipase-catalyzed synthesis of soybean fatty acid ethyl esters in pressurized propane. J Bio Technol 147:108–115

    CAS  Google Scholar 

  • Chakravorty D, Parameswaran S, Dubey VK, Patra S (2012) Unraveling the rationale behind organic solvent stability of lipases. Appl Biochem Biotechnol 167:439–461

    CAS  PubMed  Google Scholar 

  • Duarte SH, del Peso Hernández GL, Canet A, Benaiges MD, Maugeri F, Valero F (2015) Enzymatic biodiesel synthesis from yeast oil using immobilized recombinant Rhizopus oryzae lipase. Biores Technol 183:175–180

    CAS  Google Scholar 

  • Feng S, Li GL, Zhang HJ, Yan YJ, Rials T, Rooney W (2014) Enhanced performance of Rhizopusoryzae lipase immobilized on hydrophobic carriers and its application in biorefinery of rapeseed oil deodorizer distillate. Bioenerg Res 7:935–945

    Google Scholar 

  • Feng Y, Liu S, Jiao Y, Wang YL, Wang M, Du GC, Chen J (2018) Improvement of L-asparaginase thermal stability by regulating enzyme kinetic and thermodynamic states. Process Biochem 71:45–52

    CAS  Google Scholar 

  • Fernandez-Lafuente R (2010) Lipase from Thermomyces Lanuginosus: Uses and prospects as an industrial biocatalyst. J Mol Catal B Enzyme 62:197–212

    CAS  Google Scholar 

  • Fu XF, Zheng JY, Ying XX, Yan HD, Wang Z (2014) Investigation of lipozyme TL IM-catalyzed transesterification using ultraviolet spectrophoto metric assay. Chin J Catal 35:553–559

    CAS  Google Scholar 

  • Gandhi A, Vania Anisya A, Muhammad S, Heri H (2017) Effect of chitosan’s amino group in adsorption-crosslinking immobilization of lipase enzyme on resin to catalyze biodiesel synthesis. Energy Procedia 136:47–52

    Google Scholar 

  • Garcia-Galan C, Berenguer-Murcia Á, Fernandez-Lafuente R, Rodrigues RC (2011) Potential of different enzyme immobilization strategies to improve enzyme performance. Adv Synth Catal 353:2885–2904

    CAS  Google Scholar 

  • Gazis A, White DJ, Page SR, Cockcroft JR (1999) Effect of oral vitamin e (α-tocopherol) supplementation on vascular endothelial function in type 2 diabetes mellitus. Diabet Med 16:304–311

    CAS  PubMed  Google Scholar 

  • Gunawan S, Kasim NS, Ju YH (2008) Separation and purification of squalene from soybean oil deodorizer distillate. Sep Purif Technol 60:128–135

    CAS  Google Scholar 

  • Gupta S, Bhattacharya A, Murthy CN (2013) Tune to immobilize lipases on polymer membranes: techniques, factors and prospects. Biocatal Agric Biotechnol 2:171–190

    Google Scholar 

  • Kamal-Eldin A, Appelqvist L (1996) The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31:671–701

    CAS  PubMed  Google Scholar 

  • Kartal F, Janssen MHA, Hollmann F (2011) Improved esterification activity of Candida rugosa lipase in organic solvent by immobilization as cross-linked enzyme aggregates (CLEAs). J Mol Catal B Enzyme 71:85–89

    CAS  Google Scholar 

  • Koutinas M, Yiangou C, Osório NM, Ioannou K, Canet A, Valero F, Ferreira-Dias S (2017) Application of commercial and non-commercial immobilized lipases for biocatalytic production of ethyl lactate in organic solvents. Biores Technol 247:496–503

    Google Scholar 

  • Li ZX, Zhang YF, Lin MM, Ouyang PK, Ge J, Liu Z (2013) Lipase-catalyzed one-step and regioselective synthesis of clindamycin palmitate. Org Process Res Dev 17:1179–1182

    CAS  Google Scholar 

  • Mahmod SS, Yusof F, Shah NH, Jami MS, Khanahmadi S (2015) Development of an immobilized biocatalyst with lipase and protease activities as a multipurpose cross-linked enzyme aggregate (multi-clea). Process Biochem 50:2144–2157

    CAS  Google Scholar 

  • Na X, Anuj GS, Bo L, Thamonwan A, Eric AD (2019) Impact of phospholipid-tocopherol combinations and enzyme-modified lecithin on the oxidative stability of bulk oil. J Agric Food Chem 67:7954–7960

    Google Scholar 

  • Nasaruddin RR, Alam MZ, Jami MS (2014) Evaluation of solvent system for the enzymatic synthesis of ethanol based biodiesel from sludge palm oil (SPO). Biores Technol 154:155–161

    CAS  Google Scholar 

  • Pöhnlein M, Hausmann R, Lang S, Syldatk C (2015) Enzymatic synthesis and modification of surface-active glycolipids. Eur J Lipid Sci Technol 117:145–155

    Google Scholar 

  • Qin L, Zeng Q, Zhang J, Cheng H, Chen L, Qi Z (2017) Integrated process for extracting vitamin E with high purity from the methylated oil deodorizer distillate. Sep Purif Technol 196:229–236

    Google Scholar 

  • Roddy LG, Shanke V (1993) Immobilised nucleases. Crit Rev Biotechnol 13:255–273

    Google Scholar 

  • Rodrigues J, Canet A, Rivera I, Osório NM, Sandoval G, Valero F, Ferreira-Dias S (2016) Biodiesel production from crude jatropha oil catalyzed by non-commercial immobilized heterologous Rhizopus oryzae and Carica papaya lipases. Biores Technol 213:88–95

    CAS  Google Scholar 

  • Royon D, Daz M, Ellenrieder G, Locatelli S (2007) Enzymatic production of biodiesel from cotton seed oil using t-butanol as a solvent. Biores Technol 98:648–653

    CAS  Google Scholar 

  • Sheldon RA (2007) Enzyme immobilization: the quest for optimum performance. Adv Synth Catal 38:1289–1307

    Google Scholar 

  • Skjold-Jorgensen J, Vind J, Svendsen A, Bjerrum MJ (2014) Altering the activation mechanism in Thermomyces lanuginosus Lipase. Biochem 53:4152–4160

    Google Scholar 

  • Soto ID, Escobar S, Mesa M (2017) Study of the physicochemical interactions between Thermomyces lanuginosus lipase and silica-based supports and their correlation with the biochemical activity of the biocatalysts. Mat Sci Eng C Mater 79:525–532

    CAS  Google Scholar 

  • Sun J, Ding C, Zheng JY, Yu XJ, Wang Z (2017) Improved enantioselective esterification of DL-menthol catalyzed by immobilized TL 100L lipase. J Mol Catal B Enzyme 133:S271–S276

    Google Scholar 

  • Torres CF, Torrelo G, Señorans FJ, Reglero G (2007) A two steps enzymatic procedure to obtain sterol esters, tocopherols and fatty acid ethyl esters from soybean oil deodorizer distillate. Process Biochem 42:1335–1341

    CAS  Google Scholar 

  • Torres MPG, Foresti ML, Ferreira ML (2013) Effect of different parameters on the hydrolytic activity of cross-linked enzyme aggregates (CLEAs) of lipase from Thermomyces lanuginosa. Bio Chem Eng J 72:18–23

    CAS  Google Scholar 

  • Wang L, Du W, Liu D, Li L, Dai N (2007) Lipase-catalyzed biodiesel production from soybean oil deodorizer distillate with absorbent present in tert-butanol system. J Mol Catal B Enzyme 43:29–32

    CAS  Google Scholar 

  • Watanabe Y, Nagao T, Hirota Y, Kitano M, Shimada Y (2004) Purification of tocopherols and phytosterols by a two-step in situ enzymatic reaction. J Am Oil Chem Soc 81:339–345

    CAS  Google Scholar 

  • Xia H, Zhong X, Li ZX, Jiang YB (2019) Palladium-mediated hybrid biocatalysts with enhanced enzymatic catalytic performance via allosteric effects. J Colloid Interf Sci 533:1–8

    CAS  Google Scholar 

  • Yadav GD, Dhoot SB (2009) Immobilized lipase-catalysed synthesis of cinnamyl laurate in non-aqueous media. J Mol Catal B Enzyme 57:34–39

    CAS  Google Scholar 

  • Yang X, Zheng P, Ni Y, Sun Z (2012) Highly efficient biosynthesis of sucrose-6-acetate with cross-linked aggregates of lipozyme TL 100L. J Biotechnol 161:27–33

    CAS  PubMed  Google Scholar 

  • You QH, Yin XL, Zhao YP, Zhang Y (2013) Biodiesel production from jatropha oil catalyzed by immobilized Burkholderia cepacia lipase on modified attapulgite. Biores Technol 148:202–207

    CAS  Google Scholar 

  • Yücel Y, Demir C, Dizge N, Keskinle B (2014) Methods for lipase immobilization and their use for biodiesel production from vegetable oil. Energ Source Part A 36:1203–1211

    Google Scholar 

  • Zhang X, Yu J, Zeng A (2017) Optimization and modeling for the synthesis of sterol esters from deodorizer distillate by lipase-catalyzed esterification. Biotechnol Appl Bioc 64:270–278

    CAS  Google Scholar 

  • Zheng GW, Yu HL, Li CX, Pan J, Xu JH (2011) Immobilization of Bacillus subtilis esterase by simple cross-linking for enzymatic resolution of dl-menthyl acetate. J Mol Catal B Enzym 70:138–143

    CAS  Google Scholar 

Download references

Acknowledgements

This research was financially supported by National Natural Science Foundation of China (31600639, 31660247), key research and development program of Zhejiang Province (2019C01082) and the Education Department of Jiangxi Province (GJJ151211).

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Conceptualization, JZ and ZW; Data curation, JZ and ZW; Funding acquisition, JZ and XL; Investigation, WW, SW, XL and YZ; Supervision, ZW; Writing original draft, JZ and WW.

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Correspondence to Zhao Wang.

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Zheng, J., Wei, W., Wang, S. et al. Immobilization of Lipozyme TL 100L for methyl esterification of soybean oil deodorizer distillate. 3 Biotech 10, 51 (2020). https://doi.org/10.1007/s13205-019-2028-6

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