Pseudomonas fluorescens AK lipase was in situ immobilized on MCM-48-type mesoporous material employing the ionic liquid 1-hexadecyl-3-methylimidazolium chloride as a template for the inorganic material synthesis and also as an additive in the enzyme immobilization for lipase as a catalyst in chemical reactions—making it possible to reuse it. Storage stability, operational, and the potential for application in ester synthesis studies were performed. The support synthesis and AK lipase immobilization processes were efficient, presenting a 664% esterification yield and a 578 U/g enzymatic activity with 4 continuous reuse cycles, in addition to a conversion to the ester synthesis of ethyl and geranyl oleates of 14 and 18%, respectively. Thus, the results presented demonstrate the potential of using this mesoporous material in the enzymatic immobilization process.
Get full access to this article
View all access options for this article.
References
1.
XiangX, SuoH, XuC, HuY. Covalent immobilization of lipase onto chitosan-mesoporous silica hybrid nanomaterials by carboxyl functionalized ionic liquids as the coupling agent. Colloids Surf B Biointerfaces, 2018:165; 262–269.
2.
MendesAA, OliveiraPC, CastroHS. Properties and biotechnological applications of porcine pancreatic lipase. J Mol Catal B-Enzym, 2012; 78:119–134.
3.
PawongratR, XuX, H-KittikunA. Synthesis of monoacylglycerol rich in polyunsaturated fatty acids from tuna oil with immobilized lipase AK. Food Chem, 2007; 104:251–258.
4.
SilvaGS, InoueDY, DorsG, et al.Desempenho de diferentes lipases imobilizadas na síntese de biodiesel de óleo de palma. Acta Sci Techno, 2011; 33(2):197–203.
5.
TintorCB. Utilização de resíduos gordurosos para a produção de biodiesel via enzimática. Dissertação (Mestrado em Ciência e Engenharia Ambiental). Universidade Federal de Alfenas Poços de Caldas, MG, 2014.
6.
MadhavanA, SindhuR, BinodP, SukumaranRK, PandeyA. Strategies for design of improved biocatalysts for industrial applications. Bioresour Technol, 2017; 245:1304–1313.
7.
JesionowskiT, ZdartaJ, KrajewskaB. Enzyme immobilization by adsorption: A review. Adsorption, 2014; 20:801–821.
8.
LinP, WeinrichD, WaldmannH. Protein biochips: Oriented surface immobilization of proteins. Macromol Chem Phys, 2010; 211:136–144.
9.
LiuY, YuJ. Oriented immobilization of proteins on solid supports for use in biosensors and biochips: A review. Microchim Acta, 2016; 183:1–19.
10.
YanagisawaT, ShimizuT, KurodaK, KatoC. The preparation of al kyltrimethylammonium-kanemite complexes and their conversion to microporous materials. B Chem Soc Japan, 1990; 63(4):988–992.
11.
BeckJS, VartuliJC, RothWJ, et al.A new family of mesoporous molecular sieves prepared with liquid crystal templates. J Am Chem Soc, 1992; 114(27):10834–10843.
YatesTJV, Thomas JM, FernandezJJ, et al.Three-dimensional real-space crystallography of MCM-48 mesoporous silica revealed by scanning transmission electron tomography. Chem Phys Lett, 2006; 418:540.
15.
SilvaCR, WallauM, Urquieta-GonzálezEA. Mesoporous carbons prepared by nano-casting with meso- or non-porous silica nanoparticles. J Braz Chem Soc, 2006; 17(6):1170–1180.
16.
ZhangK, YuanEH, XuLL, et al.Preparation of high‐quality MCM‐48 mesoporous silica and the mode of action of the template. Eur J Inorg Chem, 2012; 4183.
17.
EimerGA, IerellaLBP, MontiGA, AnunziataOA. Synthesis and characterization of Al-MCM-41 and Al-MCM-48 mesoporous materials. Catal Lett, 2002; 78(1–4):65–75.
18.
ManjunathaK, YadavLSR, JayalakshmiT, et al.Ionic liquid assisted hydrothermal synthesis of TiO2 nanoparticles: Photocatalytic and antibacterial activity. J Mater Res Technol, 2018; 7(1):7–13.
19.
ZhaoB, ShiB, Ma R Immobilization of papain of the Mesoporous Molecular Sieve MCM-48. Eng Life Sci, 2005; 5:436–441.
20.
BattistonCSZ, FicanhaAMM, LevandoskiKLD, et al.Immobilization of lipase on mesoporous molecular sieve MCM-48 obtained using ionic solid as a structure director and esterification reaction on solvent-free. Quím Nova, 2017; 40(3):293–298.
SachseA, WuttkeC, DíazU, SouzaMO. Mesoporous Y zeolite through ionic liquid based surfactant templating. Microporous Mesopororous Mater, 2015; 217:81–86.
23.
SharifiA, BarazandehM, AbaeeMS, Mirzaei. [Omim][BF4], a green and recyclable ionic liquid medium for the one-pot chemoselective synthesis of benzoxazinones. Tetrahedron Lett, 2010; 51(14):1852–1855.
24.
Dalla-VecchiaR, NascimentoMG, SoldiV. Aplicações de lipases imobilizadas em polímeros. Quím Nova, 2004; 27(4):623–630.
25.
BassegodaA, CesariniS, DiazP. Lipase improvement: Goals and strategies. Comput and Struct Biotechnol J, 2012; 2(3):1–8.
26.
SharmaS, KanwarSS. Organic solvent tolerant lipases and applications. Sci World J, 2014; 2014:15.
27.
BradfordMM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem, 1976; 7(72):248–254.
28.
LaemmliU. K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 1970; 227(1):680.
29.
KumarD, SchumacherK, HohenescheCD, et al.MCM-41, MCM-48 and related mesoporous adsorbents: Their synthesis and characterization. Colloids Surf A, 2001; 187–188:109–116.
30.
Alonso-MoralesN, Lopez-GallegoF, BetancorL, et al.Reversible immobilization of glutaryl acylase on sepabeads coated with polyethyleneimine. Biotechnol Progress, 2008; 20(1):533–536.
31.
FerrazLR, OliveiraDS, SilvaMF, et al.Production and partial characterization of multifunctional lipases by Sporobolomyces ruberrimus using soybean meal, rice meal and sugarcane bagasse as substrates. Biocat Agr Biotechnol, 2012; 1(3):243–252.
32.
PaulaAV, BarbozaJCS, CastroHF. Estudo da influência do solvente, carboidrato e ácido graxo na síntese enzimática de ésteres de açúcares. Quím Nova, 2005; 28(5):792–796.
33.
NyariNLD, FernandesIA, Bustamante-VargasCE, et al.In situ immobilization of Candida antarctica B lipase in polyurethanefoam support. J Mol Catal B Enzym, 2016; 124:52–61.
34.
PrlainovićN, Knežević-JugovićZ, MijinD, BezbradicaD. Immobilization of lipase from Candida rugosa on Sepabeads: The effect of lipase oxidation by periodates. Bioprocess Biosyst Eng, 2011; 34(7):803–810.
35.
SilvaJMR, NascimentoMG. Epoxidação do β-cariofileno com lipases imobilizadas em gel de ágar. Quím Nova, 2014; 37(6):1022–1027.
36.
NascimentoAR, FigueredoGP, RodriguesG, et al.Síntese e caracterização de materiais mesoporosos modificados com níquel para a captura de CO2. Cerâmica, 2014; 60:482–489.
37.
TeixeiraVG, CoutinhoFMV, GomesAS. Principais métodos de caracterização da porosidade de resinas à base de divinilbenzeno. Quím Nova, 2001; 24(6):808–818.
38.
MohidemNA, MatHB. Catalytic activity and stability of laccase entrapped in sol-gel silica with additives. J Sol-Gel Sci Technol, 2012; 61(1):96–103.
39.
HaraP, MikkolaJP, MurzinDY, KanervaLT. Supported ionic liquids in Burkholderia cepacia lipase-catalyzed asymmetric acylation. J Mol Catal B Enzym, 2010; 67(1–2):129–134.
40.
CarvalhoNB, LimaAS, SoaresCMF. Uso de sílicas modificadas para imobilização de lipases. Quím Nova, 2015; 38(3):399–409.
41.
SouzaRL, FariaELP, FigueiredoRT, et al.Protic ionic liquid as additive on lipase immobilization using silica sol-gel. Enzyme Microb Technol, 2013; 52(3):141–150.
42.
FehérE, IlleováV, Kelemen-HorváthI, et al.Enzymatic production of isoamyl acetate in an ionic liquid–alcohol biphasic system. J Mol Catal B Enzym, 2008; 50(1):28–32.
43.
LerinL, CeniG, RichettiA, et al.Successive cycles of utilization of Novozym 435 in three different reaction systems. Braz J Chem Eng, 2011; 28(2):181–188.
44.
GraebinNG, MartinsAB, LorenzoniAS, et al.Immobilization of lipase B from Candida antarctica on porous styrene-divinylbenzene beads improves butyl acetate synthesis. Biotechnol Prog, 2012; 28(2):406–412.
