Click Chemistry for Biotechnology and Materials Science

417 Pages·2009·40.41 MB·English

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Click Chemistry for Biotechnology
and Materials Science
Click Chemistry for Biotechnology and Materials Science Edited by Joerg Lahann
© 2009 John Wiley & Sons, Ltd. ISBN: 978-0-470-69970-6
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Click Chemistry for
Biotechnology and
Materials Science
Editedby
JOERG LAHANN
UniversityofMichigan,AnnArbor,USA
A John Wiley and Sons, Ltd., Publication
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Thiseditionfirstpublished2009
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CoverconceptkindlyprovidedbyHimabinduNandivada(Co-author,Chapter12).
LibraryofCongressCataloging-in-PublicationData
Lahann,Joerg.
Clickchemistryforbiotechnologyandmaterialsscience/JoergLahann.
p. cm.
Includesbibliographicalreferencesandindex.
ISBN978-0-470-69970-6
1.Biotechnology. 2.Materialsscience. 3.Combinatorialchemistry.
4.Macromolecules–Synthesis. I.Title.
TP248.2.L342009
660.6–dc22 2009016549
AcataloguerecordforthisbookisavailablefromtheBritishLibrary.
ISBN(H/B): 978-0-470-69970-6
Typesetin10/12ptTimesbyAptaraInc.,NewDelhi,India.
PrintedandboundinSingaporebyFabulousPrintersPrivateLtd
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ForAimee
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Contents
Preface xiii
ListofContributors xv
Acknowledgments xix
1 ClickChemistry:AUniversalLigationStrategyforBiotechnology
andMaterialsScience 1
JoergLahann
1.1 Introduction 1
1.2 SelectedExamplesofClickReactionsinMaterialsScience
andBiotechnology 2
1.3 PotentialLimitationsofClickChemistry 5
1.4 Conclusions 5
References 6
2 CommonSynthonsforClickChemistryinBiotechnology 9
ChristineSchilling,NicoleJungandStefanBra¨se
2.1 Introduction–ClickChemistry 9
2.2 PeptidesandDerivatives 10
2.3 Peptoids 12
2.4 PeptidicDendrimers 13
2.5 Oligonucleotides 14
2.6 Carbohydrates 18
2.7 Conclusion 25
References 26
3 Copper-freeClickChemistry 29
JeremyM.BaskinandCarolynR.Bertozzi
3.1 Introduction 29
3.2 Bio-orthogonalLigations 30
3.2.1 CondensationsofKetonesandAldehydeswith
Heteroatom-boundAmines 31
3.2.2 StaudingerLigationofPhosphinesandAzides 32
3.2.3 Copper-freeAzide–AlkyneCycloadditions 35
3.2.4 BioorthogonalLigationsofAlkenes 37
3.3 ApplicationsofCopper-freeClickChemistries 38
3.3.1 Activity-basedProfilingofEnzymes 38
3.3.2 Site-specificLabelingofProteins 39
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viii Contents
3.3.3 MetabolicLabelingofGlycans 41
3.3.4 MetabolicTargetingofOtherBiomoleculeswith
ChemicalReporters 44
3.4 SummaryandOutlook 45
References 46
4 ProteinandPeptideConjugationtoPolymersandSurfacesUsing
OximeChemistry 53
HeatherD.Maynard,RebeccaM.BroyerandChristopherM.Kolodziej
4.1 Introduction 53
4.2 Protein/Peptide–PolymerConjugates 54
4.3 ImmobilizationofProteinsandPeptidesonSurfaces 60
4.4 Conclusions 66
References 67
5 TheRoleofClickChemistryinPolymerSynthesis 69
Jean-Franc¸oisLutzandBrentS.Sumerlin
5.1 Introduction 69
5.2 PolymerizationviaCuAAC 70
5.3 Post-polymerizationModificationviaClickChemistry 72
5.4 Polymer–BiomacromoleculeConjugation 76
5.5 FunctionalNanomaterials 81
5.6 SummaryandOutlook 83
References 85
6 Blocks,StarsandCombs:ComplexMacromolecularArchitecture
PolymersviaClickChemistry 89
SebastianSinnwell,AndrewJ.Inglis,MartinaH.StenzelandChristopher
Barner-Kowollik
6.1 Introduction 89
6.2 BlockCopolymers 91
6.2.1 PreparingPolymersforClickConjugations 92
6.2.2 TheClickReaction:MethodologiesandIsolation 96
6.2.3 PolymerCharacterization 99
6.3 StarPolymers 101
6.3.1 StarpolymersA 101
n
6.3.2 DentriticStarPolymers 107
6.4 GraftCopolymers 107
6.4.1 ‘Grafting-to’AzideMainChains 109
6.4.2 ‘Grafting-to’AlkyneMainChains 111
6.4.3 Non-CuAACRoutes 113
6.5 ConcludingRemarks 113
References 113
7 ClickChemistryonSupramolecularMaterials 119
WolfgangH.BinderandRobertSachsenhofer
7.1 Introduction 119
7.2 ClickReactionsonRotaxanes,CyclodextrinesandMacrocycles 123
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Contents ix
7.2.1 ClickwithRotaxanes 123
7.2.2 ClickonCyclodextrines 126
7.2.3 ClickonMacrocycles 128
7.3 ClickReactionsonDNA 131
7.4 ClickReactionsonSupramolecularPolymers 138
7.5 ClickReactionsonMembranes 143
7.6 ClickReactionsonDendrimers 147
7.7 ClickReactionsonGelsandNetworks 147
7.8 ClickReactionsonSelf-assembledMonolayers 153
References 164
8 DendrimerSynthesisandFunctionalizationbyClickChemistryfor
BiomedicalApplications 177
DanielQ.McNerny,DouglasG.Mullen,IstvanJ.Majoros,MarkM.
BanaszakHollandJamesR.BakerJr
8.1 Introduction 177
8.2 DendrimerSynthesis 181
8.2.1 DivergentSynthesis 181
8.2.2 ConvergentSynthesis 183
8.3 DendrimerFunctionalization 184
8.4 ConclusionsandFutureDirections 189
References 191
9 ReversibleDiels–AlderCycloadditionfortheDesignofMultifunctional
NetworkPolymers 195
AmyM.PetersonandGiuseppeR.Palmese
9.1 Introduction 195
9.2 DesignofPolymerNetworks 198
9.3 ApplicationofDiels–AlderLinkagestoPolymerSystems 199
9.3.1 MolecularWeightControlofLinearPolymers 200
9.3.2 RemoldableCrosslinkedMaterials 202
9.3.3 ThermallyRemovableEncapsulants 203
9.3.4 ReversiblyCrosslinkedPolymer–SolventGels 203
9.3.5 RemendableMaterials 204
9.3.6 RecyclableThermosets 206
9.3.7 SmartMaterials 207
9.4 Conclusions 209
References 209
10 ClickChemistryinthePreparationofBiohybridMaterials 217
HeatherJ.Kitto,JanLauko,FlorisP.J.T.RutjesandAlanE.Rowan
10.1 Introduction 217
10.2 Polymer-containingBiohybridMaterials 218
10.2.1 PolymersfromControlledTechniques 218
10.2.2 Bio-inspiredPolymersviaClickChemistry 220
10.3 BiohybridStructuresbasedonProteinConjugates 228
10.4 BiohybridAmphiphiles 232
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10.5 Glycoconjugates 236
10.5.1 CarbohydrateClusters 236
10.5.2 Glycopeptides 238
10.5.3 Glycopolymers 244
10.6 Conclusions 247
References 247
11 FunctionalNanomaterialsusingtheCu-catalyzedHuisgen
CycloadditionReaction 255
SanderS.vanBerkel,ArnoldW.G.Nijhuis,DennisW.P.M.Lo¨wikand
JanC.M.vanHest
11.1 Introduction 255
11.2 InorganicNanoparticles 256
11.2.1 Silicon-basedNanoparticles 256
11.2.2 CadmiumSelenide-basedNanoparticles 257
11.2.3 FerricOxide-basedNanoparticles 257
11.2.4 Gold-basedNanoparticles 261
11.3 Carbon-basedNanomaterials 266
11.3.1 Fullerenes 267
11.3.2 CarbonNanotubes 269
11.4 Self-assembledOrganicStructures 272
11.4.1 Liposomes 274
11.4.2 Polymersomes 275
11.4.3 MicellesandCross-linkedNanoparticles 278
11.5 VirusParticles 281
11.6 Conclusions 284
References 285
12 Copper-catalyzed‘Click’ChemistryforSurfaceEngineering 291
HimabinduNandivadaandJoergLahann
12.1 Introduction 291
12.2 SynthesisofAlkyneorAzide-functionalizedSurfaces 292
12.2.1 Self-assembledMonolayersofAlkanethiolates 292
12.2.2 Self-assembledMonolayersofSilanesandSiloxanes 292
12.2.3 BlockCopolymers 294
12.2.4 Layer-by-layerFilms 296
12.2.5 ChemicalVaporDepositionPolymerization 297
12.2.6 FiberNetworks 298
12.3 SpatiallyControlledClickChemistry 299
12.4 Copper-catalyzedClickChemistryforBioimmobilization 300
12.5 Summary 305
References 305
13 ClickChemistryinProteinEngineering,Design,Detection
andProfiling 309
DanielaC.DieterichandA.JamesLink
13.1 Introduction 309
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Contents xi
13.2 PosttranslationalFunctionalizationofProteinswithAzides
andAlkynes 310
13.3 CotranslationalFunctionalizationofProteinswithAzides
andAlkynes 314
13.4 BONCAT:IdentificationofNewlySynthesizedProteinsvia
NoncanonicalAminoAcidTagging 318
13.5 ConclusionsandFutureProspects 321
References 322
14 FluorogenicCopper(I)-catalyzedAzide–AlkyneCycloaddition
ReactionsReactionsandtheirApplicationsinBioconjugation 327
Ce´lineLeDroumaguetandQianWang
14.1 ClickReactionforBioconjugationApplications 327
14.2 SignificanceofFluorogenicReactionsinBioconjugation 328
14.3 CuAAC-basedFluorogenicReaction 332
14.4 ApplicationsofCuAACinBioconjugation 337
14.4.1 FluorogenicProbingofCellularComponents 339
14.4.2 FluorogenicConjugationofDNA 341
14.4.3 FluorogenicConjugationofViruses 344
14.4.4 FluorogenicConjugationofNanoparticles/Polymers 345
14.5 Conclusions 348
References 349
15 SynthesisandFunctionalizationofBiomoleculesviaClickChemistry 355
ChristineSchilling,NicoleJungandStefanBra¨se
15.1 Introduction 355
15.2 LabelingofMacromolecularBiomolecules 356
15.2.1 FluorescentLabeling 356
15.2.2 LabelingofBovineSerumAlbumin 360
15.2.3 Biotin-labelingofBiomolecules:ABPP 361
15.2.4 FluorineLabeling 364
15.3 SynthesesofNaturalProductsandDerivatives 365
15.4 EnzymesandClickChemistry 368
15.5 SynthesisofGlycosylatedMolecularArchitectures 371
15.6 SynthesisofNitrogen-richCompounds:PolyazidesandTriazoles 373
15.7 Conclusions 374
References 375
16 UnprecedentedElectro-opticPropertiesinPolymersandDendrimers
EnabledbyClickChemistryBasedontheDiels–AlderReactions 379
JingdongLuo,Tae-DongKimandAlexK.-Y.Jen
16.1 Introduction 379
16.2 Diels–AlderClickChemistryforHighlyEfficientSide-chain
E-OPolymers 380
16.3 Diels–AlderClickChemistryforCrosslinkableE-OPolymers
ContainingBinaryNLOChromophores 388
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16.4 Diels–AlderClickChemistryforNLODendrimers 392
16.5 Conclusions 394
References 397
Index 399