Lipase from pseudomonas cepacia immobilized into ZIF-8 as bio-catalyst for enantioselective hydrolysis and transesterification

Process Biochemistry - Tập 102 - Trang 132-140 - 2021
Jian Ou1, Xin Yuan1, Yu Liu1, Panliang Zhang1, Weifeng Xu1, Kewen Tang1
1Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, 414006, Hunan, China

Tài liệu tham khảo

Boussouar, 2017, Single nanochannel platform for detecting chiral, Anal. Chem., 89, 1110, 10.1021/acs.analchem.6b02682 Wang, 2019, Construction of β-cyclodextrin covalent organic framework modified chiral stationary phase for chiral separation, ACS Appl. Mater. Interfaces, 11, 48363, 10.1021/acsami.9b16720 Navarro-Sánchez, 2017, Peptide metal-organic frameworks for enantioselective separation of chiral drugs, J. Am. Chem. Soc., 139, 4294, 10.1021/jacs.7b00280 Bhatia, 2005, Chiral resolution of racemic ibuprofen ester in an enzymatic membrane reactor, J. Membr. Sci., 247, 185, 10.1016/j.memsci.2004.09.019 Bhushan, 2018, Enantioselective resolution of 2-arylpropionic acid derivatives employing immobilization of lipase from bacillus subtilis strain kakrayal_1 (BSK-L), Bioresource Technol., 269, 581, 10.1016/j.biortech.2018.08.123 Tang, 2010, Separation of flurbiprofen enantiomers by biphasic recognition chiral extraction, Chem. Eng. J., 158, 411, 10.1016/j.cej.2010.01.009 Collados, 2016, Catalytic synthesis of enantiopure chiral alcohols via addition of grignard reagents to carbonyl compounds, ACS Catal., 6, 1952, 10.1021/acscatal.5b02832 de Los Ríos, 2012, Effective resolution of 1-phenyl ethanol by candida antarctica lipase B catalysed acylation with vinyl acetate in protic ionic liquids (PILs), Green Chem., 14, 1584, 10.1039/c2gc35196j Kawakami, 2012, Application of a burkholderia cepacia lipase-immobilized silica monolith micro-bioreactor to continuous-flow kinetic resolution for transesterification of (R, S)-1-phenylethanol, Process Biochem., 47, 147, 10.1016/j.procbio.2011.09.017 Verho, 2015, Chemoenzymatic dynamic kinetic resolution: a powerful tool for the preparation of enantiomerically pure alcohols and amines, J. Am. Chem. Soc., 137, 3996, 10.1021/jacs.5b01031 Moustafa, 2018, Lipase-catalyzed dynamic kinetic resolution of C1- and C2- symmetric racemic axially chiral 2,2’-dihydroxy-1,1’-biaryls, Angew. Chem. Int. Ed., 130, 10435, 10.1002/ange.201804161 Rodrigues, 2019, Immobilization of lipases on hydrophobic supports: immobilization mechanism, advantages, problems, and solutions, Biotechnol. Adv., 37, 746, 10.1016/j.biotechadv.2019.04.003 Arana-Pea, 2021, Immobilization of lipases via interfacial activation on hydrophobic supports: production of biocatalysts libraries by altering the immobilization conditions, Catal. Today, 362, 130, 10.1016/j.cattod.2020.03.059 Monteiro, 2021, Biotechnological relevance of the lipase A from Candida antarctica, Catal. Today, 362, 141, 10.1016/j.cattod.2020.03.026 Romano, 2015, Esterases as stereoselective biocatalysts, Biotechnol. Adv., 33, 547, 10.1016/j.biotechadv.2015.01.006 Rios, 2018, Biotechnological potential of lipases from Pseudomonas: sources, properties and applications, Process Biochem., 75, 99, 10.1016/j.procbio.2018.09.003 Rodrigues, 2013, Modifying enzyme activity and selectivity by immobilization, Chem. Soc. Rev., 42, 6290, 10.1039/C2CS35231A Hudson, 2008, Proteins in mesoporous silicates, Angew. Chem. Int. Ed., 47, 8582, 10.1002/anie.200705238 Patra, 2015, Design of metal organic framework-enzyme based bioelectrodes as a novel and highly sensitive biosensing platform, J. Mater. Chem. B, 3, 8983, 10.1039/C5TB01412C Yuan, 2020, Immobilization of lipase onto metal-organic frameworks for enantioselective hydrolysis and transesterification, AIChE J., 66, 10.1002/aic.16292 Chen, 2012, Size-selective biocatalysis of myoglobin immobilized into a mesoporous metal-organic framework with hierarchical pore sizes, Inorg. Chem., 51, 9156, 10.1021/ic301280n Sahutoglu, 2015, Immobilisation of aspergillus oryzae α-amylase and aspergillus niger glucoamylase enzymes as cross-linked enzyme aggregates, Chem. Pap., 69, 433, 10.1515/chempap-2015-0031 Qiu, 2016, Encapsulation of a metal-organic polyhedral in the pores of a metal-organic framework, J. Am. Chem. Soc., 138, 1138, 10.1021/jacs.5b12189 Shen, 2018, Ordered macro-microporous metal-organic framework single crystals, Science, 359, 206, 10.1126/science.aao3403 Zhou, 2014, A novel MOF/graphene oxide composite GrO@MIL-101 with high adsorption capacity for acetone, J. Mater. Chem. A, 2, 4722, 10.1039/C3TA15086K Gong, 2014, Solution processable MOF yellow phosphor with exceptionally high quantum efficiency, J. Am. Chem. Soc., 136, 16724, 10.1021/ja509446h Yao, 2019, On-demand CO release for amplification of chemotherapy by MOF functionalized magnetic carbon nanoparticles with NIR irradiation, Biomaterials, 195, 51, 10.1016/j.biomaterials.2018.12.029 Yasutaka, 2011, Enhancement in adsorption and catalytic activity of enzymes immobilized on phosphorus- and calcium-modified MCM-41, J. Phys. Chem. B, 115, 10335, 10.1021/jp203632g He, 2016, Construction of thermophilic lipase-embedded metal-organic frameworks via biomimetic mineralization: a biocatalyst for ester hydrolysis and kinetic resolution, ACS Appl. Mater. Interfaces, 8, 24517, 10.1021/acsami.6b05538 Niknam Shahrak, 2017, Zeolitic imidazolate framework-8 for efficient adsorption and removal of Cr(VI) ions from aqueous solution, Environ. Sci. Pollut. Res., 24, 9624, 10.1007/s11356-017-8577-5 Lykourinou, 2011, Immobilization of MP-11 into a mesoporous metal-organic framework, MP-11@mesoMOF: a new platform for enzymatic catalysis, J. Am. Chem. Soc., 133, 10382, 10.1021/ja2038003 Tong, 2013, Application and comparison of high performance liquid chromatography and high speed counter-current chromatography in enantioseparation of (±)-2-phenylpropionic acid, J. Chromatogr. A, 1281, 79, 10.1016/j.chroma.2013.01.056 Jiang, 2016, Adsorption toward trivalent rare earth element from aqueous solution by zeolitic imidazolate frameworks, Ind. Eng. Chem. Res., 55, 6365, 10.1021/acs.iecr.6b00422 Liu, 2013, Novel trypsin–FITC@MOF bioreactor efficiently catalyzes protein digestion, J. Mater. Chem. B, 1, 928, 10.1039/c3tb00257h He, 2014, Facile synthesis of zeolitic imidazolate framework-8 from a concentrated aqueous solution, Microporous Mesoporous Mater., 184, 55, 10.1016/j.micromeso.2013.10.003 Lian, 2016, Coupling two enzymes into a tandem nanoreactor utilizing a hierarchically structured MOF, Chem. Sci., 7, 6969, 10.1039/C6SC01438K Cheong, 2017, Facile fabrication of a stable and recyclable lipase@amine-functionalized ZIF-8 nanoparticles for esters hydrolysis and transesterification, J. Nanopart. Res., 19, 280, 10.1007/s11051-017-3979-3 Shieh, 2015, Imparting functionality to biocatalysts via embedding enzymes into nanoporous materials by a de novo approach: size-selective sheltering of catalase in metal-organic framework microcrystals, J. Am. Chem. Soc., 137, 4276, 10.1021/ja513058h Mu, 2014, Poly(2-vinyl-4,4-dimethylazlactone)-functionalized magnetic nanoparticles as carriers for enzyme immobilization and its application, ACS Appl. Mater. Interfaces, 6, 21346, 10.1021/am5063025 Jiang, 2017, Enhanced catalytic stability of lipase immobilized on oxidized and disulfide-rich eggshell membrane for esters hydrolysis and transesterification, Int. J. Biol. Macromol., 105, 1328, 10.1016/j.ijbiomac.2017.07.166 Abdulla, 2013, Immobilized burkholderia cepacia lipase for biodiesel production from crude Jatropha curcas L. oil, Biomass Bioenerg., 56, 8, 10.1016/j.biombioe.2013.04.010 Chen, 2011, Activity enhancement and stabilization of lipase from pseudomonas cepacia in polyallylamine-mediated biomimetic silica, Biotechnol. Lett., 33, 525, 10.1007/s10529-010-0451-1 Li, 2018, Biodiesel production via trans-esterification using pseudomonas cepacia immobilized on cellulosic polyurethane, ACS Omega, 3, 6804, 10.1021/acsomega.8b00110 Dias, 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 Kumar, 2019, Biodiesel production from hybrid non-edible oil using bio-support beads immobilized with lipase from pseudomonas cepacian, Fuel, 255, 10.1016/j.fuel.2019.115801 Xie, 1998, Effect of water content on enzyme activity and enantioselectivity of lipase-catalyzed esterification of racemic ibuprofen in organic solvents, Ann. NY. Acad. Sci., 864, 570, 10.1111/j.1749-6632.1998.tb10383.x Klibanov, 1995, What is remembered and why?, Nature, 374, 596, 10.1038/374596a0 Stepankova, 2013, Strategies for stabilization of enzymes in organic solvents, ACS Catal., 3, 2823, 10.1021/cs400684x Zhong, 2017, Synthesis and characterization of mesoporous Cu-MOF for laccase immobilization, J. Chem. Technol. Biotechnol., 92, 1841, 10.1002/jctb.5189 Xue, 2007, Lipase immobilized on HOOC-MCF: a highly enantioselective catalyst for transesterification resolution of (R, S)-1-phenylethanol, Chin. Chem. Lett., 8, 929, 10.1016/j.cclet.2007.06.005 Han, 2016, Immobilization of lipase from Pseudomonas fluorescens on porous polyurea and its application in kinetic resolution of racemic 1-phenylethanol, ACS Appl. Mater. Interfaces, 8, 25714, 10.1021/acsami.6b07979 Li, 2013, Novel bioreactor for resolution of (R, S)-1-phenylethanol using the functional conducting polymer and ionic liquid with excellent catalytic activity and stability, J. Chem. Technol. Biotechnol., 88, 2091, 10.1002/jctb.4077 Bai, 2012, Immobilization of lipase on aminopropyl-grafted mesoporous silica nanotubes for the resolution of (R, S)-1-phenylethanol, J. Mol. Catal. B-Enzym., 76, 82, 10.1016/j.molcatb.2011.11.005 Li, 2013, Improving activity and enantioselectivity of lipase via immobilization on macroporous resin for resolution of racemic 1- phenylethanol in non-aqueous medium, BMC Biotechnol., 13, 92, 10.1186/1472-6750-13-92 Hoffmann, 2011, Enantioselective resolution of (R, S)-1-phenylethanol catalyzed by lipases immobilized in starch films, J. Brazil. Chem. Soc., 22, 1559, 10.1590/S0103-50532011000800021