固定化漆酶降解水中酚类污染物的研究进展
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摘要
叙述了漆酶的特点及其来源、固定漆酶的载体材料及漆酶降解水中酚类污染物的研究进展。总结了漆酶降解酚类化合物反应动力学的研究方法,分析了固定漆酶磁性载体的优势、漆酶降解酚类化合物的反应机理及效果。认为漆酶因具有能传递电子的铜离子,能将酚类化合物羟基上的电子脱去使其形成自由基,并将分子氧还原成水致使酚类化合物降解,漆酶是降解酚类化合物的最佳选择之一;磁性载体凭借其特有磁力可把漆酶高效固定具有极大的应用潜力。今后的研发重点包括系统研究漆酶与底物的结合机制,低成本高性能载体材料的研发,以及漆酶的规模化生产及其在废水处理中的规模化应用等。
The research progress of the characteristics and sources of laccase, the carrier materials of immobilized laccase and the degradation of phenol pollutants in water by laccase were described. The kinetics of enzymatic degradation of phenolic compounds by laccase was summarized, and the advantages of fixed magnetic carrier of laccase, the mechanism and effect of laccase degradation were analyzed. For laccase have passed electronics copper ions, the electron on hydroxyl of phenolic compounds can be take off to form free radicals, and molecular oxygen reduction into water that phenolic compounds can be degraded, laccase is one of the best choice for phenolic compounds degradation, thought magnetic carrier, with its unique magnetic force can be fixed the laccase high efficiency has a great application potential. The research and development focus in future including research of the combination mechanism of laccase and substrate system, the low cost and high performance carrier materials, as well as the large-scale production of laccase and its large-scale application in wastewater treatment.
The research progress of the characteristics and sources of laccase, the carrier materials of immobilized laccase and the degradation of phenol pollutants in water by laccase were described. The kinetics of enzymatic degradation of phenolic compounds by laccase was summarized, and the advantages of fixed magnetic carrier of laccase, the mechanism and effect of laccase degradation were analyzed. For laccase have passed electronics copper ions, the electron on hydroxyl of phenolic compounds can be take off to form free radicals, and molecular oxygen reduction into water that phenolic compounds can be degraded, laccase is one of the best choice for phenolic compounds degradation, thought magnetic carrier, with its unique magnetic force can be fixed the laccase high efficiency has a great application potential. The research and development focus in future including research of the combination mechanism of laccase and substrate system, the low cost and high performance carrier materials, as well as the large-scale production of laccase and its large-scale application in wastewater treatment.
引文
[1]李惠惠,韩香,司玉昌.水中酚类有机污染物的检测方法研究进展[J].广东化工,2018,45(1):108-110.
[2]WANG B,HUANG B,JIN W,et al.Occurrence,distribution,and sources of six phenolic endocrine disrupting chemicals in the 22 river estuaries around Dianchi Lake in China[J].Environmental Science&Pollution Research International,2013,20(5):3185-3194.
[3]SEVERI G,MORRIS H A,MACINNIS R J,et al.Circulating steroid hormones and the risk of prostate cancer[J].Cancer Epidemiol Biomarkers Prev,2006,15(1):86-91.
[4]STOKER C,REY F,RODRIGUEZ H,et al.Sex reversal effects on Caiman latirostris exposed to environmentally relevant doses of the xenoestrogen bisphenol A[J].General&Comparative Endocrinology,2003,133(3):287-296.
[5]任丽,王国俊.用超临界流体萃取和固相萃取分析水中酚类污染物[J].分析化学,1997,25(10):1172-1176.
[6]周弛,王斐,张会强,等.HPLC和HPLC-MS/MS测定地表水中酚类化合物[J].环境监测管理与技术,2016,28(4):46-49.
[7]黄崇瑶,彭放,严旭晖,等.苯酚废水净化研究进展[J].广州化工,2018,46(2):12-15.
[8]PATSIAS J,PAPADAKIS E N,PAPADOPOULOU-MOURKIDOUE.Analysis of phenoxyalkanoic acid herbicides and their phenolic conversion products in soil by microwave assisted solvent extraction and subsequent analysis of extracts by on-line solid-phase extractionliquid chromatography[J].Journal of Chromatography A,2002,959(1/2):153-161.
[9]LACORTE S,BARCELO D.Rapid degradation of fenitrothion in estuarine waters[J].Environmental Science&Technology,1994,28(6):1159-1163.
[10]宋志慧,孙欣欣,李捍东.氯代酚类物质对斑马鱼的急性毒性及QSAR研究[J].环境科学与技术,2014,37(12):20-24.
[11]张泽雄,刘红艳,邢贺,等.漆酶可降解底物种类的研究进展[J].生物技术通报,2017,33(10):97-102.
[12]王馥丽,赵鹏,裴承新,等.漆酶及其应用研究进展[J].生命科学仪器,2017,15(5):19-24.
[13]甘淑娴.漆酶在水处理中的研究进展和专利分析[J].广东化工,2015,42(14):143.
[14]NADAROGLU H,TASGIN E.Purification and characterisation of laccase from lactarius volemus and its application in removal of phenolic compounds from fruit juice[J].Journal of Food Agriculture&Environment,2013,11(3):109-114.
[15]UPADHYAY P,SHRIVASTAVA R,AGRAWAL P K.Bioprospecting and biotechnological applications of fungal laccase[J].Biotech,20166(1):15.
[16]WITAYAKRAN S.Laccase in organic synthesis and its applications[J].Dissertations&Theses-Gradworks,2008.
[17]WANG S,ZHANG A L,LI X P,et al.Study on advanced treatment of pulping and papermaking process efluent by immobilized laccase[J].Advanced Materials Research,2011,233/235:712-715.
[18]PEZZELLA C,GUARINO L,PISCITELLI A.How to enjoy laccases[J].Cellular&Molecular Life Sciences,2015,72(5):923-40.
[19]DENG H M,SHAO K,LIANG J H,et al.Source of laccase and research progress on carriers for laccase immobilization[J].Biotechnology Bulletin,2017.
[20]相欣然,黄和,胡燚.纳米复合材料固定化酶的研究进展[J].无机化学学报,2017,33(1):1-15.
[21]MOHAMMADI M,AS'HABI M A,SALEHI P,et al.Immobilization of laccase on epoxy-functionalized silica and its application in biodegradation of phenolic compounds[J].International Journal of Biological Macromolecules,2018,109:443-447.
[22]REKUC'A,BRYJAK J,SZYMAN'SKA K,et al.Very stable silicagel-bound laccase biocatalysts for the selective oxidation in continuous systems[J].Bioresource Technology,2010,101(7):2076-83.
[23]MOHIDEM N A,MAT H B.Catalytic activity and stability of laccase entrapped in sol-gel silica with additives[J].Journal of Sol-Gel Science and Technology,2012,61(1):96-103.
[24]CHAMPAGNE P P,RAMSAY J A.Dye decolorization and detoxification by laccase immobilized on porous glass beads[J].Bioresource Technology,2010,101(7):2230-2235.
[25]覵OBARZEWSKI J.The immobilized and soluble form of fungal peroxidase.Comparison of physico-chemical properties[J].Biotechnology&Bioengineering,2004,23(9):2161-2165.
[26]JOLIVALT C,BRENON S,CAMINADE E,et al.Immobilization of laccase from Trametes versicolor on a modified PVDF microfiltration membrane:characterization of the grafted support and application in removing a phenylurea pesticide in wastewater[J].Journal of Membrane Science,2000,180(1):103-113.
[27]JIANG D S,LONG S Y,HUANG J,et al.Immobilization of Pycnoporus sanguineus laccase on magnetic chitosan microspheres[J].Biochemical Engineering Journal,2005,25(1):15-23.
[28]LU L,ZHAO M,WANG Y.Immobilization of laccase by alginatechitosan microcapsules and its use in dye decolorization[J].World Journal of Microbiology&Biotechnology,2007,23(2):159-166.
[29]KALKAN N A,AKSOY S,AKSOY E A,et al.Preparation of chitosancoated magnetite nanoparticles and application for immobilization of laccase[J].Journal of Applied Polymer Science,2012,123(2):707-716.
[30]欧阳科,谢珊,赵雅,等.磁性Fe3O4/石墨烯异质结固定漆酶特性及其对水中双酚A的降解研究[J].生态环境学报,2015,24(1):106-112.
[31]AMIN R,KHORSHIDI A,SHOJAEI A F,et al.Immobilization of laccase on modified Fe3O4@Si O2@Kit-6 magnetite nanoparticles for enhanced delignification of olive pomace bio-waste[J].Int J Biol Macromol,2018,114:106-113.
[32]SNCHEZ-RAMREZJ,MARTNEZ-HERNNDEZJL,LPEZ-CAMPOSR G,et al.Laccase validation as pretreatment of Agave waste prior to saccharification:free and immobilized in superparamagnetic nanoparticles enzyme preparations[J].Waste and Biomass Valorization,2018,9(2):223-234.
[33]VISHNU D,NEERAJ G,SWAROOPINI R,et al.Synergetic integration of laccase and versatile peroxidase with magnetic silica microspheres towards remediation of biorefinery wastewater[J].Environ Sci Pollut Res Int,2017,24(22):17993-18009.
[34]WU D,MEI F,QU S,et al.Studies of the reaction between laccase and hydroquinone by microcalorimetry[J].Thermochimica Acta,1990,169(11):203-208.
[35]谢修银,颜承农,吴鼎泉,等.漆酶与各种类型底物反应性能的微量热法研究[J].华中师范大学学报(自然科学版),1999(2):246-249.
[36]FERN NDEZ-S NCHEZ C,TZANOV T,G BITZ G M,et al.Voltammetric monitoring of laccase-catalysed mediated reactions[J].Bioelectrochemistry,2002,58(2):149-156.
[37]CUSOLA O,VALLS C,VIDAL T,et al.Using electrochemical methods to study the kinetics of laccase-catalyzed oxidation of phenols[J].Industrial&Engineering Chemistry Research,2018,57(6):2434-2439.
[38]钟平方,彭惠民,彭方毅,等.漆酶催化酚类?苯胺类化合物的动力学分析及其测定废水中邻苯二酚的应用研究[J].环境科学,2010,31(11):2673-2677.
[39]CLEMMER J D,GILLILAND B L,BARTSCH R A,et al.Substituent effects on the electron transfer reactivity of hydroquinones with laccase blue copper[J].Biochimica et Biophysica Acta(BBA)-Enzymology,1979,568(2):307-320.
[40]齐艳兵,朱吉人,孙尧金,等.漆酶与酚类模式底物的结合及反应活性的理论研究[C].苏州:第七届国际分子模拟与信息技术应用学术会议,2014.
[41]RANGELOV S,NICELL J A.A model of the transient kinetics of laccase-catalyzed oxidation of phenol at micromolar concentrations[J].Biochemical Engineering Journal,2015,99:1-15.
[42]RANGELOV S,NICELL J A.Modelling the transient kinetics of laccase-catalyzed oxidation of four aqueous phenolic substrates at low concentrations[J].Biochemical Engineering Journal,2018,132.
[43]周攀登,付时雨.漆酶催化对苯基苯酚的聚合[J].高分子学报,2004,1(4):614-616.
[44]陈辉,张剑波,王维敬,等.固定化漆酶催化去除水中2,4-二氯苯酚[J].北京大学学报(自然科学版),2006,42(4):484-489.
[45]XU R,ZHOU Q,LI F,et al.Laccase immobilization on chitosan/poly(vinyl alcohol)composite nanofibrous membranes for2,4-dichlorophenol removal[J].Chemical Engineering Journal,2013,222(15):321-329.
[46]DOGAN T,BAYRAM E,UZUN L,et al.Trametes versicolor laccase immobilized poly(glycidyl methacrylate)based cryogels for phenol degradation from aqueous media[J].Journal of Applied Polymer Science,2015,132(20).
[47]XU R,TANG R,ZHOU Q,et al.Enhancement of catalytic activity of immobilized laccase for diclofenac biodegradation by carbon nanotubes[J].Chemical Engineering Journal,2015,262:88-95.
[48]DAI Y,YAO J,SONG Y,et al.Enhanced adsorption and degradation of phenolic pollutants in water by carbon nanotubes modified laccase-carrying electrospun fibrous membranes[J].Environmental Science Nano,2016,3(4).
[49]XU R,CUI J,LI F,et al.Removal of 2,4,6-trichlorophenol by Laccase immobilized on nano-copper incorporated electrospun fibrous membrane-high efficiency,stability and reusability[J].Chemical Engineering Journal,2017,326.
[50]张陈成,韩萍芳.活性碳纤维固定化漆酶及其处理苯酚废水的研究[J].印染助剂,2017,34(5):21-23.
[2]WANG B,HUANG B,JIN W,et al.Occurrence,distribution,and sources of six phenolic endocrine disrupting chemicals in the 22 river estuaries around Dianchi Lake in China[J].Environmental Science&Pollution Research International,2013,20(5):3185-3194.
[3]SEVERI G,MORRIS H A,MACINNIS R J,et al.Circulating steroid hormones and the risk of prostate cancer[J].Cancer Epidemiol Biomarkers Prev,2006,15(1):86-91.
[4]STOKER C,REY F,RODRIGUEZ H,et al.Sex reversal effects on Caiman latirostris exposed to environmentally relevant doses of the xenoestrogen bisphenol A[J].General&Comparative Endocrinology,2003,133(3):287-296.
[5]任丽,王国俊.用超临界流体萃取和固相萃取分析水中酚类污染物[J].分析化学,1997,25(10):1172-1176.
[6]周弛,王斐,张会强,等.HPLC和HPLC-MS/MS测定地表水中酚类化合物[J].环境监测管理与技术,2016,28(4):46-49.
[7]黄崇瑶,彭放,严旭晖,等.苯酚废水净化研究进展[J].广州化工,2018,46(2):12-15.
[8]PATSIAS J,PAPADAKIS E N,PAPADOPOULOU-MOURKIDOUE.Analysis of phenoxyalkanoic acid herbicides and their phenolic conversion products in soil by microwave assisted solvent extraction and subsequent analysis of extracts by on-line solid-phase extractionliquid chromatography[J].Journal of Chromatography A,2002,959(1/2):153-161.
[9]LACORTE S,BARCELO D.Rapid degradation of fenitrothion in estuarine waters[J].Environmental Science&Technology,1994,28(6):1159-1163.
[10]宋志慧,孙欣欣,李捍东.氯代酚类物质对斑马鱼的急性毒性及QSAR研究[J].环境科学与技术,2014,37(12):20-24.
[11]张泽雄,刘红艳,邢贺,等.漆酶可降解底物种类的研究进展[J].生物技术通报,2017,33(10):97-102.
[12]王馥丽,赵鹏,裴承新,等.漆酶及其应用研究进展[J].生命科学仪器,2017,15(5):19-24.
[13]甘淑娴.漆酶在水处理中的研究进展和专利分析[J].广东化工,2015,42(14):143.
[14]NADAROGLU H,TASGIN E.Purification and characterisation of laccase from lactarius volemus and its application in removal of phenolic compounds from fruit juice[J].Journal of Food Agriculture&Environment,2013,11(3):109-114.
[15]UPADHYAY P,SHRIVASTAVA R,AGRAWAL P K.Bioprospecting and biotechnological applications of fungal laccase[J].Biotech,20166(1):15.
[16]WITAYAKRAN S.Laccase in organic synthesis and its applications[J].Dissertations&Theses-Gradworks,2008.
[17]WANG S,ZHANG A L,LI X P,et al.Study on advanced treatment of pulping and papermaking process efluent by immobilized laccase[J].Advanced Materials Research,2011,233/235:712-715.
[18]PEZZELLA C,GUARINO L,PISCITELLI A.How to enjoy laccases[J].Cellular&Molecular Life Sciences,2015,72(5):923-40.
[19]DENG H M,SHAO K,LIANG J H,et al.Source of laccase and research progress on carriers for laccase immobilization[J].Biotechnology Bulletin,2017.
[20]相欣然,黄和,胡燚.纳米复合材料固定化酶的研究进展[J].无机化学学报,2017,33(1):1-15.
[21]MOHAMMADI M,AS'HABI M A,SALEHI P,et al.Immobilization of laccase on epoxy-functionalized silica and its application in biodegradation of phenolic compounds[J].International Journal of Biological Macromolecules,2018,109:443-447.
[22]REKUC'A,BRYJAK J,SZYMAN'SKA K,et al.Very stable silicagel-bound laccase biocatalysts for the selective oxidation in continuous systems[J].Bioresource Technology,2010,101(7):2076-83.
[23]MOHIDEM N A,MAT H B.Catalytic activity and stability of laccase entrapped in sol-gel silica with additives[J].Journal of Sol-Gel Science and Technology,2012,61(1):96-103.
[24]CHAMPAGNE P P,RAMSAY J A.Dye decolorization and detoxification by laccase immobilized on porous glass beads[J].Bioresource Technology,2010,101(7):2230-2235.
[25]覵OBARZEWSKI J.The immobilized and soluble form of fungal peroxidase.Comparison of physico-chemical properties[J].Biotechnology&Bioengineering,2004,23(9):2161-2165.
[26]JOLIVALT C,BRENON S,CAMINADE E,et al.Immobilization of laccase from Trametes versicolor on a modified PVDF microfiltration membrane:characterization of the grafted support and application in removing a phenylurea pesticide in wastewater[J].Journal of Membrane Science,2000,180(1):103-113.
[27]JIANG D S,LONG S Y,HUANG J,et al.Immobilization of Pycnoporus sanguineus laccase on magnetic chitosan microspheres[J].Biochemical Engineering Journal,2005,25(1):15-23.
[28]LU L,ZHAO M,WANG Y.Immobilization of laccase by alginatechitosan microcapsules and its use in dye decolorization[J].World Journal of Microbiology&Biotechnology,2007,23(2):159-166.
[29]KALKAN N A,AKSOY S,AKSOY E A,et al.Preparation of chitosancoated magnetite nanoparticles and application for immobilization of laccase[J].Journal of Applied Polymer Science,2012,123(2):707-716.
[30]欧阳科,谢珊,赵雅,等.磁性Fe3O4/石墨烯异质结固定漆酶特性及其对水中双酚A的降解研究[J].生态环境学报,2015,24(1):106-112.
[31]AMIN R,KHORSHIDI A,SHOJAEI A F,et al.Immobilization of laccase on modified Fe3O4@Si O2@Kit-6 magnetite nanoparticles for enhanced delignification of olive pomace bio-waste[J].Int J Biol Macromol,2018,114:106-113.
[32]SNCHEZ-RAMREZJ,MARTNEZ-HERNNDEZJL,LPEZ-CAMPOSR G,et al.Laccase validation as pretreatment of Agave waste prior to saccharification:free and immobilized in superparamagnetic nanoparticles enzyme preparations[J].Waste and Biomass Valorization,2018,9(2):223-234.
[33]VISHNU D,NEERAJ G,SWAROOPINI R,et al.Synergetic integration of laccase and versatile peroxidase with magnetic silica microspheres towards remediation of biorefinery wastewater[J].Environ Sci Pollut Res Int,2017,24(22):17993-18009.
[34]WU D,MEI F,QU S,et al.Studies of the reaction between laccase and hydroquinone by microcalorimetry[J].Thermochimica Acta,1990,169(11):203-208.
[35]谢修银,颜承农,吴鼎泉,等.漆酶与各种类型底物反应性能的微量热法研究[J].华中师范大学学报(自然科学版),1999(2):246-249.
[36]FERN NDEZ-S NCHEZ C,TZANOV T,G BITZ G M,et al.Voltammetric monitoring of laccase-catalysed mediated reactions[J].Bioelectrochemistry,2002,58(2):149-156.
[37]CUSOLA O,VALLS C,VIDAL T,et al.Using electrochemical methods to study the kinetics of laccase-catalyzed oxidation of phenols[J].Industrial&Engineering Chemistry Research,2018,57(6):2434-2439.
[38]钟平方,彭惠民,彭方毅,等.漆酶催化酚类?苯胺类化合物的动力学分析及其测定废水中邻苯二酚的应用研究[J].环境科学,2010,31(11):2673-2677.
[39]CLEMMER J D,GILLILAND B L,BARTSCH R A,et al.Substituent effects on the electron transfer reactivity of hydroquinones with laccase blue copper[J].Biochimica et Biophysica Acta(BBA)-Enzymology,1979,568(2):307-320.
[40]齐艳兵,朱吉人,孙尧金,等.漆酶与酚类模式底物的结合及反应活性的理论研究[C].苏州:第七届国际分子模拟与信息技术应用学术会议,2014.
[41]RANGELOV S,NICELL J A.A model of the transient kinetics of laccase-catalyzed oxidation of phenol at micromolar concentrations[J].Biochemical Engineering Journal,2015,99:1-15.
[42]RANGELOV S,NICELL J A.Modelling the transient kinetics of laccase-catalyzed oxidation of four aqueous phenolic substrates at low concentrations[J].Biochemical Engineering Journal,2018,132.
[43]周攀登,付时雨.漆酶催化对苯基苯酚的聚合[J].高分子学报,2004,1(4):614-616.
[44]陈辉,张剑波,王维敬,等.固定化漆酶催化去除水中2,4-二氯苯酚[J].北京大学学报(自然科学版),2006,42(4):484-489.
[45]XU R,ZHOU Q,LI F,et al.Laccase immobilization on chitosan/poly(vinyl alcohol)composite nanofibrous membranes for2,4-dichlorophenol removal[J].Chemical Engineering Journal,2013,222(15):321-329.
[46]DOGAN T,BAYRAM E,UZUN L,et al.Trametes versicolor laccase immobilized poly(glycidyl methacrylate)based cryogels for phenol degradation from aqueous media[J].Journal of Applied Polymer Science,2015,132(20).
[47]XU R,TANG R,ZHOU Q,et al.Enhancement of catalytic activity of immobilized laccase for diclofenac biodegradation by carbon nanotubes[J].Chemical Engineering Journal,2015,262:88-95.
[48]DAI Y,YAO J,SONG Y,et al.Enhanced adsorption and degradation of phenolic pollutants in water by carbon nanotubes modified laccase-carrying electrospun fibrous membranes[J].Environmental Science Nano,2016,3(4).
[49]XU R,CUI J,LI F,et al.Removal of 2,4,6-trichlorophenol by Laccase immobilized on nano-copper incorporated electrospun fibrous membrane-high efficiency,stability and reusability[J].Chemical Engineering Journal,2017,326.
[50]张陈成,韩萍芳.活性碳纤维固定化漆酶及其处理苯酚废水的研究[J].印染助剂,2017,34(5):21-23.