Bioconjugating Technique英文资料.pdf

Bioconjugating Technique英文资料.pdf

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BioconjugateTechniques2ndEditionThispageintentionallyleftblankBioconjugateTechniques2ndEditionGregT.HermansonPierceBiotechnology,ThermoFisherScientific,Rockford,Illinois,USAAMSTERDAMBOSTONHEIDELBERGLONDONNEWYORKOXFORDPARISSANDIEGOSANFRANCISCOSINGAPORESYDNEYTOKYOAcademicPressisanimprintofElsevierThemolecularmodelonthecoverisanitritereductaseenzymeobtainedfromtheRCSBProteinDataBank（2afn）,asdeterminedbyMurphy,M.E.,Turley,S.,Kukimoto,M.,Nishiyama,M.,Horinouchi,S.,Sasaki,H.,Tanokura,M.,andAdman,E.T.（1995）StructureofAlcaligenesfaecalisnitritereductaseandacoppersitemutant,M150E,thatcontainszinc.Biochemistry34,1210712117.Thespace-fillingmodelwascreatedfromthecoordinatefileusingPovChemandthefinalimageray-tracedusingPOV-RayAcademicPressisanimprintofElsevier84TheobaldsRoad,LondonWC1X8RR,UKRadarweg29,POBox211,1000AEAmsterdam,TheNetherlands30CorporateDrive,Suite400,Burlington,MA01803,USA525BStreet,Suite1900,SanDiego,CA92101-4495,USAFirstedition1996Secondedition2008Copyright2008ElsevierInc.AllrightsreservedNopartofthispublicationmaybereproduced,storedinaretrievalsystemortransmittedinanyformorbyanymeanselectronic,mechanical,photocopying,recordingorotherwisewithoutthepriorwrittenpermissionofthepublisher.PermissionsmaybesoughtdirectlyfromElseviersScience&TechnologyRightsDepartmentinOxford,UK:

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/selectingObtainingpermissiontouseElseviermaterialNoticeNoresponsibilityisassumedbythepublisherforanyinjuryand/ordamagetopersonsorpropertyasamatterofproductsliability,negligenceorotherwise,orfromanyuseoroperationofanymethods,products,instructionsorideascontainedinthematerialherein.BritishLibraryCataloguinginPublicationDataAcataloguerecordforthisbookisavailablefromtheBritishLibraryLibraryofCongressCataloging-in-PublicationDataAcatalogrecordforthisbookisavailablefromtheLibraryofCongressISBN:

978-0-12-370501-3TypesetbyCharonTecLtd（AMacmillanCompany）,Chennai,IPrintedandboundintheUnitedStatesofAmerica080910111098765432ForinformationonallAcademicPresspublicationsvisitourwebsiteatForAmyandMeghan,who,sincethefirsteditionwaspublished,havenowbecomeinterestedinpursuingcareersinmicrobiologyandmedicine.viContentsOverviewPARTIBioconjugateChemistry1.FunctionalTargets32.TheChemistryofReactiveGroups169PARTIIBioconjugateReagents3.Zero-LengthCrosslinkers2154.HomobifunctionalCrosslinkers2345.HeterobifunctionalCrosslinkers2766.TrifunctionalCrosslinkers3367.DendrimersandDendrons3468.CleavableReagentSystems3919.FluorescentProbes39610.BifunctionalChelatingAgentsandRadioimmunoconjugates49811.BiotinylationReagents50612.IodinationReagents54613.SilaneCouplingAgents56214.MicroparticlesandNanoparticles58215.Buckyballs,Fullerenes,andCarbonNanotubes62716.MassTagsandIsotopeTags64917.ChemoselectiveLigation:

BioorthogonalReagents66618.DiscretePEGReagents707PARTIIIBioconjugateApplications19.PreparationofHaptenCarrierImmunogenConjugates74520.AntibodyModificationandConjugation78321.ImmunotoxinConjugationTechniques82422.PreparationofLiposomeConjugatesandDerivatives85823.AvidinBiotinSystems90024.PreparationofColloidalGold-LabeledProteins92425.ModificationwithSyntheticPolymers93626.EnzymeModificationandConjugation96127.NucleicAcidandOligonucleotideModificationandConjugation96928.BioconjugationintheStudyofProteinInteractions1003viiDetailedContentsPrefacetotheSecondEditionxxiiiPrefacetotheFirstEditionxxviAcknowledgmentsxxviiiHealthandSafetyxxixIntellectualPropertyxxxPARTIBioconjugateChemistry1.FunctionalTargets1.ModificationofAminoacids,Peptides,andProteins31.1.ProteinStructureandReactivity4AminoAcids4NucleophilicReactionsandthepIofAminoAcidSideChains13Secondary,Tertiary,andQuaternaryStructure15ProstheticGroups,Cofactors,andPost-TranslationalModifications19ProtectingtheNativeConformationandActivityofProteins21OxidationofAminoAcidsinProteinsandPeptides23SolventAccessibilityofFunctionalTargetsinProteins291.2.ProteinCrosslinkingMethods322.ModificationofSugars,Polysaccharides,andGlycoconjugates352.1.CarbohydrateStructureandFunctionality36BasicSugarStructure37SugarFunctionalGroups39PolysaccharideandGlycoconjugateStructure442.2.CarbohydrateandGlycanConjugationMethods493.ModificationofNucleicAcidsandOligonucleotides503.1.PolynucleotideStructureandFunctionality51NucleotideFunctionalGroups53RNAandDNAStructure623.2.PolynucleotideCrosslinkingMethods664.CreatingSpecificFunctionalities664.1.IntroductionofSulfhydrylResidues（Thiolation）67ModificationofAmineswith2-Iminothiolane（TrautsReagent）67ModificationofAmineswithSATA71ModificationofAmineswithSATP74viiiDetailedContentsModificationofAmineswithSPDP76ModificationofAmineswithSMPT77ModificationofAmineswithN-AcetylHomocysteineThiolactone80ModificationofAmineswithSAMSA81ModificationofAldehydesorKetoneswithAMBH83ModificationofCarboxylatesorPhosphateswithCystamine84ModificationofProteinswithCystamine87ModificationofNucleicAcidsandOligonucleotideswithCystamine87UseofDisulfideReductants87CompleteReductionofDisulfidesinProteinMoleculesUsingDTT90UseofDTTtoCleaveDisulfide-ContainingCrosslinkingAgents91EllmansAssayfortheDeterminationofSulfhydryls1004.2.IntroductionofCarboxylateGroups101ModificationofAmineswithAnhydrides102ModificationofSulfhydrylswithIodoacetate109ModificationofSulfhydrylswithBMPA111ModificationofHydroxylswithChloroaceticAcid1134.3.IntroductionofPrimaryAmineGroups114ModificationofCarboxylateswithDiamines114ModificationofSulfhydrylswithN-（?

-Iodoethyl）trifluoroacetamideAminoethyl-8118ModificationofSulfhydrylswithEthylenimine119ModificationofSulfhydrylswith2-Bromoethylamine120ModificationofSulfhydrylswith2-Aminoethyl-2?

-aminoethanethiolsulfonate121ModificationofCarbohydrateswithDiamines122ModificationofAlkylphosphateswithDiamines124ModificationofAldehydeswithAmmoniaorDiamines124IntroductionofArylaminesonPhenolicCompounds125AmineDetectionReagents1274.4.IntroductionofAldehydeResidues129PeriodateOxidationofGlycolsandCarbohydrates130OxidaseModificationofSugarResidues131ModificationofAmineswithNHS-Aldehydes（SFBandSFPA）132ModificationofAmineswithGlutaraldehyde134PeriodateOxidationofN-TerminalSerineorThreonineResidues1364.5.IntroductionofHydrazineorHydrazideFunctionalities139ModificationofAldehydeswithBis-HydrazideCompounds140ModificationofCarboxylateswithBis-HydrazideCompounds142ModificationofAmineswithSANH,SHNH,orSHTH143ModificationofAlkylphosphateswithBis-HydrazideCompounds1464.6.IntroductionofSaccharideorGlycanGroups147ModificationofAmineswithMono（lactosylamido）mono（succinimidyl）suberate149ModificationofAmineorHydrazideMoleculesbyCarbohydratesandGlycans150LabelingGlycanswithFluorescent2-Aminopyridine,2-AminoBenzamide,orAnthranilicAcid153SynthesisofGlycosylaminesforConjugatingGlycans1555.BlockingSpecificFunctionalGroups1565.1.BlockingAmineGroups157DetailedContentsixSulfo-NHSAcetate157AceticAnhydride158CitraconicAnhydride159MaleicAnhydride1595.2.BlockingSulfhydrylGroups160N-EthylMaleimide160IodoacetateDerivatives161SodiumTetrathionate161MethylMethanethiosulfonate163EllmansReagent164DipyridylDisulfideReagents1655.3.BlockingAldehydeGroups166ReductiveAminationwithTrisorEthanolamine1665.4.BlockingCarboxylateGroups167TrisorEthanolamineplusEDC1672.TheChemistryofReactiveGroups1.AmineReactions1691.1.Isothiocyanates1701.2.Isocyanates1701.3.AcylAzides1711.4.NHSEsters1711.5.SulfonylChlorides1731.6.AldehydesandGlyoxals1731.7.EpoxidesandOxiranes1741.8.Carbonates1751.9.ArylatingAgents1751.10.Imidoesters1761.11.Carbodiimides1761.12.Anhydrides1781.13.FluorophenylEsters1791.14.HydroxymethylPhosphineDerivatives1801.15.GuanidinationofAmines1812.ThiolReactions1822.1.HaloacetylandAlkylHalideDerivatives1822.2.Maleimides1832.3.Aziridines1842.4.AcryloylDerivatives1842.5.ArylatingAgents1852.6.Thiol-DisulfideExchangeReagents185PyridylDisulfides186TNB-Thiol187xDetailedContentsDisulfideReductants1872.7.VinylsulfoneDerivatives1882.8.Metal-ThiolDativeBonds1882.9.NativeChemicalLigation1912.10.CisplatinModificationofMethionineandCysteine1923.CarboxylateReactions1923.1.DiazoalkanesandDiazoacetylCompounds1933.2.Carbonyldiimidazole1943.3.Carbodiimides1954.HydroxylReactions1954.1.EpoxidesandOxiranes1954.2.Carbonyldiimidazole1964.3.N,N?

-DisuccinimidylCarbonateorN-HydroxysuccinimidylChloroformate1964.4.OxidationwithPeriodate1974.5.EnzymaticOxidation1984.6.AlkylHalogens1984.7.Isocyanates1995.AldehydeandKetoneReactions2005.1.HydrazineDerivatives2005.2.SchiffBaseFormation2005.3.ReductiveAmination2015.4.MannichCondensation2016.ActiveHydrogenReactions2026.1.DiazoniumDerivatives2026.2.MannichCondensation2036.3.IodinationReactions2037.Photo-ChemicalReactions2047.1.ArylAzidesandHalogenatedArylAzides2047.2.Benzophenones2057.3.Anthraquinones2057.4.CertainDiazoCompounds2077.5.DiazirineDerivatives2087.6.PsoralenCompounds2088.CycloadditionReactions2108.1.DielsAlderReaction2108.2.Com