微波辐射-酶耦合催化(MIECC)反应

:20064,:200663(No.20476038)(2006)(BK2006021)33e2mail:[e-mail]2(MIECC)333(214036),,2,,:O64412;O643132;Q55:A:10052281X(2007)02P320250206MicrowaveIrradiation2EnzymeCouplingCatalysisXiaYongmeiSunShiyuFangYun33MinRuiWuHongpingZhangYue(SchoolofChemicalandMaterialEngineering,SouthernYangtzeUniversity,Wuxi214036,China)AbstractApplingmicrowaveirradiationtonon2aqueousenzymaticcatalysiscanbringmanyinterestingfindings,whichisquitedifferentfromthoseobservedfromconventionalheatingassistedenzymaticreactions.Theprogressinmicrowaveirradiation2enzymecouplingcatalysisisreviewed.Theevidenceofnon2thermaleffectgeneratedbymicrowaveirradiation,effectofmicrowaveirradiationonenzymeformationandactivity,effectofmicrowaveirradiationonkinetics,enantioselectivity,substrateselectivity,andregionselectivityinthereactionsarediscussedaswell.Inmostofthecases,microwaveirradiationdoesnotreduceenzymesactivityandimprovesreactionrateinstead,butinfluencestheenzymespecificity.Keywordsmicrowaveirradiation;enzymes;catalysis;non2thermaleffect;enantioselectivity;substrateselectivity;regioselectivity;kinetics1986Gedye[1],,,[24]1990,,,[510],,,2(microwaveirradiation2enzymecouplingcatalysis,MIECC)[1120][2127][2835][36239]MIECC1300MHz300GHz(1m1mm),192P320073PROGRESSINCHEMISTRYVol.19No.2P3Mar.,2007(),2145GHz(1212cm)[11],[12][11,13],[11,13]:,,;,,,,[1419,20]62,72(1)[18]:(1)(),;,(2)(),,(3)162[18]Fig.1Microwave2assistedregiospecificsynthesisof62substitutedpterins[18]MIECC,,,MIECC,n2MIECC[9,10]MIECC2,[21]MIECC,,[16,2226]211,MIECCProcelli[16]S2(S2adenosyl2homocysteine(AdoHcy)hydrolase),AdoHcyhydrolase280nm340nm280nm(),340nmNADHAdoHcyhydrolase,ProcelliVukova[22](acetylcholinesterase),2,2,[23]:,,,,212Procelli[16],S2(S2adenosyl2homocysteine(AdoHcy)hydrolase)52(52methlthioadenosine(MTA)phosphorylase)Tris2HCl;,(0101013mgPml)1522P32(MIECC),:AdoHcyhydrolase,KClKHSO4;MTAphosphorylase,KClNaCl,KHSO4Na2SO4Cara[24]2(2galactosidase)1h(70),20%:,,(1050gPml),,50gPml,,:,,;,,Chen[25]He2Ne(amylase)(transaminase)(proteinase),Soysal[26],Novozym435[27],()()()(),6,,;,[23]Lipolase100L200W,,6min,,,,,(),,,,2,,,,3MIECC,311Parker[5]cutinase,01580169,23;0197,;(subtilisin)2(2chymotrypsin)6[18],211417logP(),(VmPVc),VmPVclogPpH3,pH,Novozym4352163[29],Zhu[30,31]252193,,115213[33]:,,312MIECC,,Pujic[20]MIECC,[23]n2,3MIECC,215415,Lin[33],Cubiquitin50%30%Khobragade[34]PP,,,Novozym435[26],,[35]Novozym435,,,,313Yadav[36]Novozym435,Ping2PongBi2Bi,,[37][35]MIECClipozymeRMIM(LRI)n2n2,Ping2PongBi2Bi,,Ping2PongBi2Bi,()2Ping2PongBi2Bi[35]Fig.2SchematicPing2PongBi2Bimechanism[35]4,MIECC,411Lin[6]porcinepancreaticlipase(PPL)1,2,3,4221212(R23),39714,,(3)[6]Carrilo2Munoz[19]12,,ee216419[23]23522P32(MIECC)3[6]Fig.3Lipase2catalyzedacylationofmentholbymicrowaveirradiation[6]S22ee%,58185%:[6,8],,,,,,,;,,412Bradoo[38],712Bacillusstearothermophiluslipase(BSL)Burkholderiacepacialipase(BCL),Vacek[39]4(Lipozyme,M.miehei,C.cylindracea,P.cepacia),;4413Zarevcka[40](),22D222D2,[35]n2,1,3(Novozym435)n2,Novozym4351,35,MIECCMIECC,,MIECC,,MIECC[41],,[1]GedyeR,SmithF,WestawaK.TetrahedronLett.,1986,27(3):279283[2]LoupyA,PerreuxL,LiagreM,etal.PureAppl.Chem.,2001,73(1):161166[3]FavrettoL,NugentWA,LiciniG.TetrahedronLett.,2002,43:25812584[4]MarwahP,MarwahA,LardyHA.Tetrahedron,2003,59:22732287[5]ParkerMC,BessonT,LamareS,LegoyMD.TetrahedronLett.,1996,37(46):83838388[6]LinG,LinWY.TetrahedronLett.,1998,39:43334336[7]RoyI,GuptaMN.Curr.Sci.,2003,85:16851693[8](CaiHC),(FangY),(XiaYM).(ChineseJournalofOrganicChemistry),2003,23:298304[9](CaiHC),(GaoH),(FangY).(ActaChimicaSinica),2004,62:923928[10]HuangW,XiaYM,FangY.J.Mol.Catal.B:Enzym.,2005,35:113116[11]HozA,MorenoA.Chem.Soc.Rev.,2005,34(2):164178[12](JinQH).(MicrowaveChemistry).:(Beijing:SciencePress),1999.14614745219[13]LidstromP,TiemeyJ,WatheyB.Tetrahedron,2001,57:92259283[14]MingosDM,BagurstDR.Chem.Soc.Rev.,1991,20:147[15](HuangKM),(HuXM),(TangJX).(ChemicalJournalofChineseUniversities),1996,17:764768[16]ProcelliM,CacciapuotiG,FuscoS,etal.FEBSLett.,1997,402:102106[17](SunXJ),(SuYZ),(JinFM).(J.JiangsuInstitutePetrochemicalTechnology),2000,12(3):4245[18]GoswamiS,AdakAK.TetrahedronLetters,2002,43(46):83718373[19]Carrillo2MunozJR,BouvetD,Guidb2JampelE,etal.J.Org.Chem.,1996,61:77467750[20]PujicMG,JampelEG,LoupyA,etal.J.Chem.Soc.PerkinTrans.,1996,1:27772780[21]BiniM,CheccucciA,MillantaL,etal.J.Microw.Power,1978,13:9599[22]VukovaT,AtanassovA,IvanovR,etal.MedicalScienceMonitor,2005,11:5056[23](CaiHC).(MSDissertationofSouthernYangtzeUniversity),2004[24]CaraFL,ScarfiMR,SabatoDA.Bioelectromagnetics,1999,20:172176[25]ChenYP,LiuYJ,WangXL,etal.J.IntegrativePlantBiology,2005,47(7):849855[26]SoysalC,SÊoyleemezZ.J.FoodEng.,2005,68:349356[27]RjasseB,LamareS,LegoyMD.Org.Biomol.Chem.,2004,2:10861089[28]RoyI,GuptaMN.Tetrahedron,2003,59(29):54315436[29]YadavGD,LathiPS.Synth.Commun.,2005,35:16991705[30]ZhuSD,YuZN,WuYX.ProcessBiochem.,2005,40:30823086[31]ZhuSD,YuZN,WuYX,etal.Chem.Eng.Commun.,2005,192(8):15591566[32]MondalK,RoyI,GuptaMN.Biocatal.Biotransfor.,2004,22:916[33]LinSS,WuCH.J.Am.Soc.MassSpectrom.,20