芳香族硝基化合物的微生物降解

©1994-2010ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.(863)(No.2007AA061502)33e2mail:[e-mail]31,2112133(11230026;21250100),,:X506;X172:A:10052281X(2009)02P320534206MicrobialDegradationofNitroaromaticCompoundsTengShaoxiang1,2ShengGuoping1LiuXianwei1WangShuguang2YuHanqing133(11EnvironmentalEngineeringLaboratory,DepartmentofChemistry,UniversityofScienceandTechnologyofChina,Hefei230026,China;21SchoolofEnvironmentalScienceandEngineering,ShandongUniversity,Jinan250100,China)AbstractNitroaromaticcompoundsproducedthroughalargenumberofindustrialprocesses,mostnotablyinthepesticides,dyesandexplosives,areonecategoryofenvironmentalcontaminants.Biodegradationisaneffectivewaytoremovenitroaromaticsfrompollutedenvironments.Manyeffortshavebeenmadetoinvestigatethemechanismandapplicationofbiodegradationofnitroaromaticcompounds.Thispaperreviewestheresearchadvancesinbiodegradationofnitroaromaticsontheaspectsofmicroorganisms,degradationpathwaysandmechanisms,thermodynamicsandkinetics,aswellastheapplicationinbioremediation.Thefutureresearchesonbiodegradationofnitroarmaticcompoundsincludingengineeringplantstoexpressbacterialenzymesforuseinbioremediationprogramsarediscussed.Keywordsnitroaromaticcompounds;biodegradation;enzyme;thermodynamicsContents1Introduction2Microorganismsassociatedwithnitroaromatictransformation3Microbialdegradationpathways311Oxidizeddegradationpathways31111Monooxygenasecatalyzedreactions31112Dioxygenasecatalyzedreactions312Reductivedegradationpathways31211Reductionofthenitrogroups31212Reductionofthearomaticring4Kineticandthermodynamicanalysesofthedegradationpathways5Bioremediationtechnologies6Perspectives1,2,4,62(TNT)212P320093PROGRESSINCHEMISTRYVol.21No.2P3Mar.,2009©1994-2010ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.:[1],;,,,,,,,213,,[30]311311111953,Simpson42NO-2,1,42,,2[31,32]31112,NO-222321Table1Strainsforthebiodegradationofnitroaromaticcompoundssubstratemicroorganismref2,4,62trinitrotoluenePseudomonassp1JLR112Desulfovibriosp13Clostridiumthermoaceticum4Klebsiellasp.C15Methylobacteriumsp.BJ0016Bovinerumenmicrobes7AcinetobacterjuniiA88Pseudomonasfluorescence9P.aeruginosa10nitrocatecholBurkholderiacepaciaRKJ200112,62dinitrotolueneBurkholderiasp.122,42dinitrotolueneBurkholderiacepaciaJS850HydrogenophagapaleroniiJS863122,42dinitrophenolRhodococcussp.13nitrophenolKlebsiellapnuemoniae14Pseudomonassp.15Pseudomonasputida16Phanerochaetechrysosporium17ArthrobacterprotophormiaeRKJ10018NocardioidesNSP4119hexahydro21,3,52trinitro21,3,52triazineKlebsiellapneumoniaestrainSCZ21Clostridiumacetobutylicumextract2021Rhodococcussp.strainDN2222Phanerochaetechrysosporium23nitrobenzoateBurkholderiacepaciaPB4andRalstoniapauculaSB424PseudomonasputidaTW325Arthrobacterprotophormiae26nitrobenzeneComamonassp.JS76527Pseudomonassp.JX16528PseudomonaspseudoalcaligenesJS4529[3335]Johnson2,42(2,42DNT),1[36]DNTDNT(dntAaAbAcAd)Rieske,3:(Aa)(Ab)(AcAd)42252(dntB)2,4,52(THT)THT(dntD)2,4225226222,422,4225226222,42dntGdntEA312,5352P3©1994-2010ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.[36]Fig.1Themetabolismof2,42dinitrotoluenecatalysedbyBurkholderiacepaciaR34.Compoundsinbracketsremainhypothetical[36],,,TNT31211(2)[37],O2,2[37]Fig.2Reductionofnitrogroupsbyone2electronortwo2electronmechanisms[37]()[3840],NADPH2P4502NADP+NADH2Q[4143],()NAD(P)H:DT2[44,45]3TNT[46],,NO2COOHCH3HOHNH2[47],TNT(HADNT)(ADNT)(DANT)TNT[4850],TNT2,4,62(TAT)[51]3TNT[46]Fig.3DegradationpathwayofTNTthroughreductionofnitrogroups[46]63521©1994-2010ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.(opacus)erythropolisHLPM21Nocard2iodessimplexFJ221A,4R1(opacus)erythropolisHLPM21[46]F4202(NpdI),Meisenheimer(H-2PA);H-2PANpdCPNpdGMeisenheimer2H-2PANocardiodessimplexFJ221A,[52]NpdH,2H-2PA,NO2-,2,42DNPMeisenheimer[52,53]4R1(opacus)erythropolisHLPM21:(a);(b)H-2PA;(c)2H-2PA;(d)(e)2H-2PA;(f)H-22,42DNP[46]Fig.4Proposedpicric2acid2degradationpathwayinR1(opacus)erythropolisHLPM21:(a)picricacid(PA);(b)hydride2Meisenheimercomplex(H-2PA);(c)dihydride2Meisenheimercomplex(2H-2PA);(d)and(e)tautomericformsoftheprotonated2H-2PA;(f)hydride2Meisenheimercomplexof2,42dinitrophenol(H-22,42DNP)[46]TNTTNTR.(opacus)erythropolisHLPM21H-2TNT2H-2TNT[54],,2H-2TNTEnterobactercloacaePB2PseudomonasfluorescensI2CTNTNO2-[9,55]4,pHO2ZhangHughesDNT,pH[56],DNTC7H6O4N2+51621O2+010296PO43-010296C60H87O23N12P+11557H++11645NO2-+51227CO2+01936H2OpHDNT,O2CO27352P3©1994-2010ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.(Ks=93mol,max=01011h-1)5,,TNT,TNTTNTTNT[5759],TNTTNT,2[6064]2,TNT,[61,62,65]TNT,,TNT[66,67]6,,,:(1),,;(2);(3),;(4)[1]KanekarP,DoudpureP,SarnaikS.IndianJ.Exp.Biol.,2003,41:9911001[2]EsteveNA,RamosJL.Environ.Sci.Technol.,1998,32:38023808[3]DrzyzgaO,BrunsND,GorontzyT,etal.Chemosphere,1999,38:20812095[4]HuangS,LindahlPA,WangC,etal.Appl.Environ.