Metallofoldamers: Supramolecular Architectures from Helicates to Biomimetics

455 Pages·2013·15.706 MB·English

Metallofoldamers
Metallofoldamers
Supramolecular Architectures
from Helicates to Biomimetics
Edited By
GALIA MAAYAN
Schulich Faculty of Chemistry, Technion - Israel Institute of
Technology, Israel
and
MARKUS ALBRECHT
Institut fu¨r Organische Chemie, RWTH Aachen, Germany
Thiseditionfirstpublished2013
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ISBN:9780470973233
Setin10/12pt,TimesbyThomsonDigital,Noida,India
Contents
ListofContributors xi
Foreword xiii
Preface xv
1 MetalloproteinsandMetallopeptides–NaturalMetallofoldamers 1
VasilikiLykourinouandLi-JuneMing
1.1 Introduction 1
1.2 Metalloproteins 2
1.2.1 MetalloproteinsareNature’s“Metallofoldamers!” 2
1.2.2 Metal-TriggeredConformationalChangeofProteins 3
1.2.3 ConformationalChangeofMetalloproteinsCausedby
LigandBinding 7
1.2.4 ProteinMisfolding:CausesandImplications–Cu,
Zn-SuperoxideDismutase 10
1.3 Metallopeptides 12
1.3.1 AntibioticMetallopeptides 13
1.3.2 MetallopeptidesinNeurodegenerativeDiseases 20
1.3.3 OtherMetallopeptides 24
1.4 ConclusionandPerspectives 28
Acknowledgements 30
References 30
2 IntroductiontoUnnaturalFoldamers 51
ClaudiaTomasiniandNicolaCastellucci
2.1 GeneralDefinitionofFoldamers 51
2.2 BioticFoldamers 53
2.2.1 HomogeneousFoldamers 53
2.2.2 b-Peptides 53
2.2.3 g-Peptides 59
2.2.4 HybridFoldamers 60
2.2.5 AliphaticUreaFoldamers 63
2.2.6 Foldamersofa-AminoxyAcids 64
2.2.7 FoldamersContainingAmidoGroups 65
2.3 AbioticFoldamers 70
vi Contents
2.4 OrganizationInducedbyExternalAgents 72
2.4.1 OrganizationInducedbySolvents 72
2.4.2 OrganizationInducedbyAnions 73
2.5 Applications 78
2.6 ConclusionsandOutlook 81
References 81
3 Self-AssemblyPrinciplesofHelicates 91
JosefHamacek
3.1 Introduction 91
3.2 ThermodynamicConsiderationsinSelf-Assembly 93
3.2.1 MononuclearCoordinationComplexes 93
3.2.2 ExtensiontoPolynuclearEdifices 96
3.3 CooperativityinSelf-Assembly 100
3.3.1 AllostericCooperativity 101
3.3.2 ChelateCooperativity 102
3.3.3 InterannularCooperativity 104
3.4 KineticAspectsofMulticomponentOrganization 104
3.5 UnderstandingSelf-AssemblyProcesses 108
3.5.1 AssessmentofCooperativity 108
3.5.2 ThermodynamicModelling 110
3.5.3 SolvationEnergiesandElectrostaticInteractions 115
3.6 SecondaryStructureandStabilizingInteractions 118
3.7 Conclusions 118
References 120
4 StructuralAspectsofHelicates 125
MartinBergandArneL€utzen
4.1 Introduction 125
4.2 StructuralDynamics 127
4.3 TemplateEffects 129
4.4 SequenceSelectivity 130
4.5 Self-SortingEffectsinHelicateFormation 135
4.6 DiastereoselectivityI–“Meso”-HelicateversusHelicateFormation 138
4.7 DiastereoselectivityII–EnantiomericallyPureHelicatesfromChiral
Ligands 139
4.7.1 2,20-BipyridineLigands 140
4.7.2 2,20:60,200-Terpyridineand2,20:60,200:600,2-QuaterpyridineLigands 143
4.7.3 2-PyridylimineLigands 144
4.7.4 FurtherHexadentateN-DonorLigands 144
4.7.5 OxazolineLigands 144
4.7.6 P-DonorLigands 145
4.7.7 HydroxamicAcidLigands 147
Contents vii
4.7.8 b-DiketonateLigands 147
4.7.9 CatecholateLigandsandOtherDianionicLigandUnits 148
4.7.10 Non-CovalentlyAssembledLigandStrands 150
4.8 SummaryandOutlook 150
References 151
5 HelicalStructuresFeaturingThiolatoDonors 159
F.EkkehardtHahnandDennisLewing
5.1 Introduction 159
5.2 CoordinationChemistryofBis-andTris(Benzene-o-Dithiolato)Ligands 162
5.2.1 MononuclearChelateComplexes 162
5.2.2 DinuclearDouble-StrandedComplexes 165
5.2.3 DinuclearTriple-StrandedComplexes 167
5.2.4 CoordinationChemistryofTripodalTris(Benzene-o-Dithiolato)
Ligands 172
5.3 CoordinationChemistryofMixedBis(Benzene-o-Dithiol)/Catechol
Ligands 176
5.3.1 DinuclearDouble-StrandedComplexes 176
5.3.2 DinuclearTriple-StrandedComplexes 178
5.4 SubcomponentSelf-AssemblyReactions 181
5.5 SummaryandOutlook 186
References 186
6 PhotophysicalPropertiesandApplicationsofLanthanoidHelicates 193
Jean-ClaudeG.B€unzli
ListofAcronymsandAbbreviations 193
6.1 Introduction 194
6.2 HomometallicLanthanoidHelicates 197
6.2.1 InfluenceoftheTriplet-StateEnergyonQuantumYields 198
6.2.2 RadiativeLifetimeandNephelauxeticEffect 203
6.2.3 Site-SymmetryAnalysis 206
6.2.4 EnergyTransferbetweenLanthanoidIons 208
6.2.5 LanthanoidLuminescentBioprobes 210
6.2.6 OtherInvestigatedHelicates 219
6.3 Heterometallicd-fHelicates 223
6.3.1 BasicPhotophysicalProperties 223
6.3.2 EuIII-to-CrIIIEnergyTransfer 227
6.3.3 Controloff-MetalIonPropertiesbyd-TransitionMetalIons 228
6.3.4 SensitizingNIR-EmittingLanthanoidIons 235
6.4 ChiralHelicates 236
6.5 ExtendedHelicalStructures 239
6.6 Perspectives 240
Acknowledgements 241
References 241
viii Contents
7 DesignofSupramolecularMaterials:Liquid-CrystallineHelicates 249
RaymondZiessel
7.1 Introduction 249
7.2 Imino-BipyridineandImino-PhenanthrolineHelicates 252
7.2.1 LiquidCrystalsfromImino-PolypyridineBasedHelicates 257
7.3 Conclusions 266
7.4 OutlookandPerspectives 267
Acknowledgements 268
References 268
8 Helicates,Peptide-HelicatesandMetal-AssistedStabilization
ofPeptideMicrostructures 275
MarkusAlbrecht
8.1 Introduction 275
8.2 SelectedExamplesofMetalPeptideConjugates 276
8.3 HelicatesandPeptide-Helicates 279
8.3.1 Helicates 279
8.3.2 Peptide-Helicates 281
8.4 Metal-AssistedStabilizationofPeptideMicrostructures 288
8.4.1 LoopsandTurns 288
8.4.2 a-Helices 292
8.4.3 b-Sheets 297
8.5 Conclusion 298
References 300
9 ArtificialDNADirectedtowardSyntheticMetallofoldamers 303
GuidoH.CleverandMitsuhikoShionoya
9.1 Introduction 303
9.1.1 OligonucleotidesareNaturalFoldamers 303
9.1.2 BiologicalFunctionsandBeyond 305
9.1.3 DNANanotechnology 306
9.1.4 InteractionsofDNAwithMetalIons 308
9.2 TheQuestforAlternativeBasePairingSystems 309
9.2.1 ModificationsoftheHydrogenBondingPattern 310
9.2.2 ShapeComplementarity 310
9.2.3 MetalCoordination 310
9.3 DesignandSynthesisofMetalBasePairs 311
9.3.1 RationalDesignofMetalBasePairs 311
9.3.2 ModelStudies 312
9.3.3 SynthesisofModifiedNucleosides 312
9.3.4 AutomatedOligonucleotideSynthesis 314
9.3.5 EnzymaticOligonucleotidesSynthesis 315
9.4 AssemblyandAnalysisofMetalBasePairsInsidetheDNADoubleHelix 315
9.4.1 StrategiesforMetalIncorporation 315
9.4.2 AnalyticalCharacterizationinSolution 316
9.4.3 X-RayStructureDetermination 317
Contents ix
9.5 ArtificialDNAforSyntheticMetallofoldamers 318
9.5.1 Overview 318
9.5.2 TheHydroxypyridoneBasePair 320
9.5.3 TheSalenBasePair 320
9.5.4 TheImidazole,Triazoleand1-Deazaadenine-Thymine
BasePairs 323
9.6 Functions,ApplicationsandFutureDirections 324
9.6.1 DuplexStabilizationandConformationalSwitching 324
9.6.2 SensorApplications 325
9.6.3 MagnetismandElectricalConductance 325
9.6.4 FutureDirections 326
References 327
10 MetalComplexesasAlternativeBasePairsorTripletsinNatural
andSyntheticNucleicAcidStructures 333
ArnieDeLeon,JingKong,andCatalinaAchim
10.1 Introduction 333
10.2 BriefOverviewofSyntheticAnaloguesofDNA:PNA,LNA,UNA,
andGNA 338
10.3 Metal-Containing,Ligand-ModifiedNucleicAcidDuplexes 340
10.3.1 DesignStrategy 341
10.3.2 DuplexesContainingOneAlternativeMetal–LigandBase
PairwithIdenticalLigands 342
10.3.3 DuplexesContainingOneAlternativeMetal–LigandBase
PairwithDifferentLigands 359
10.4 DuplexesContainingMultipleMetalComplexes 361
10.5 Metal-Containing,Ligand-ModifiedNucleicAcidTriplexes 367
10.6 SummaryandOutlook 367
Acknowledgement 369
Abbreviations 369
References 370
11 InteractionofBiomimeticOligomerswithMetalIons 379
GaliaMaayan
11.1 Introduction 380
11.2 Single-StrandedOligomersinWhichMetalCoordination
Templates,orTemplatesandNucleatestheFormationofan
AbioticHelix 381
11.3 FoldedOligomersinWhichMetalCoordinationNucleatesthe
FormationofanAbioticSingle-StrandedHelix 384
11.4 FoldedOligomersinWhichMetalCoordinationEnhances
SecondaryStructureandLeadstoHigher-OrderArchitectures 393
11.4.1 MetalCoordinationinFoldedAromaticAmideOligomers 394
11.4.2 MetalCoordinationinPeptidomimeticFoldamers 396
11.5 ConcludingRemarks 402
References 402
x Contents
12 ApplicationsofMetallofoldamers 407
YanZhao
12.1 Introduction 407
12.2 MetallofoldamersinMolecularRecognition 409
12.3 MetallofoldamersasSensorsforMetalIons 414
12.4 MetallofoldamersasDynamicMaterials 419
12.5 ConclusionsandOutlook 429
References 430
Index 433
List of Contributors
CatalinaAchim, DepartmentofChemistry,CarnegieMellonUniversity,USA
MarkusAlbrecht, Institutf€urOrganischeChemie,RWTHAachenUniversity,Germany
Martin Berg, Kekul(cid:2)e Institute of Organic Chemistry and Biochemistry, University of
Bonn,Germany
Jean-Claude G. Bu€nzli, Institute of Chemical Sciences and Engineering, E(cid:2)cole Poly-
techniqueF(cid:2)ed(cid:2)eraledeLausanne,Switzerland
Photovoltaic Materials, Department of Materials Chemistry, Korea University, Sejong
Campus
NicolaCastellucci, DipartimentodiChimica“G.Ciamician”,Universit(cid:3)adiBologna,Italy
GuidoH.Clever, InstituteforInorganicChemistry,Georg-AugustUniversityG€ottingen,
Germany
ArnieDeLeon, DepartmentofChemistry,CarnegieMellonUniversity,USA
F. Ekkehardt Hahn, Institut f€ur Anorganische und Analytische Chemie, Westf€alische
Wilhelms-Universit€atM€unster,Germany
Josef Hamacek, Department of Inorganic and Analytical Chemistry, University of
Geneva,Switzerland
JingKong, DepartmentofChemistry,CarnegieMellonUniversity,USA
Dennis Lewing, Institut f€ur Anorganische und Analytische Chemie, Westf€alische
Wilhelms-Universit€atM€unster,Germany
Arne Lu€tzen, Kekul(cid:2)e Institute of Organic Chemistry and Biochemistry, University of
Bonn,Germany
VasilikiLykourinou, DepartmentofChemistry,UniversityofSouthFlorida,USA
Galia Maayan, Schulich Faculty of Chemistry, Technion – Israel Institute of Technol-
ogy,Israel
Li-JuneMing, DepartmentofChemistry,UniversityofSouthFlorida,USA
MitsuhikoShionoya, DepartmentofChemistry,UniversityofTokyo,Japan
Claudia Tomasini, Dipartimento di Chimica “G. Ciamician”, Universit(cid:3)a di Bologna,
Italy