Details

Sequence-Controlled Polymers


Sequence-Controlled Polymers


1. Aufl.

von: Jean-François Lutz

151,99 €

Verlag: Wiley-VCH
Format: PDF
Veröffentl.: 20.11.2017
ISBN/EAN: 9783527806119
Sprache: englisch
Anzahl Seiten: 817

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Beschreibungen

Edited by a leading authority in the field, the first book on this important and emerging topic provides an overview of the latest trends in sequence-controlled polymers. Following a brief introduction, the book goes on to discuss various synthetic approaches to sequence-controlled and biological polymers, including genetic polymers, peptide polymers and biohybrids, as well as single-chain nanoparticles. Moreover, different polymerization techniques, such as anionic and cationic as well as radical chain growth mechanism, are explained, before concluding with a look at the future for sequence-controlled polymers. With its unique coverage of this interdisciplinary field, the text will prove invaluable to polymer and environmental chemists, as well as biochemists and bioengineers.
1 Defining the Field of Sequence-Controlled Polymers 1Jean-François Lutz 1.1 Introduction 1 1.2 Glossary 4 1.3 Sequence Regulation in Biopolymers 7 1.3.1 Nucleic Acids 7 1.3.2 Proteins 7 1.4 Bio-Inspired Sequence-Regulated Approaches 8 1.5 Sequence Regulation in Synthetic Macromolecules 9 1.5.1 Step-Growth Polymerizations 11 1.5.2 Chain-Growth Polymerizations 11 1.5.3 Multistep Growth Polymerizations 13 1.6 Characterization of SCPs 15 1.7 Impact in Materials Science 17 1.8 SomeWords About the Future 19 References 20 2 Kinetics and Thermodynamics of Sequence Regulation 27Pierre Gaspard 2.1 Introduction 27 2.2 Generalities 28 2.2.1 Characterization of Sequences and Information 28 2.2.1.1 Single-Molecule Level of Description 28 2.2.1.2 Many-Molecule Level of Description 29 2.2.2 Precise or Loose Sequence Control during Copolymerization 30 2.2.3 Conditions for Growth or Dissolution 31 2.2.4 Kinetic Equations 32 2.3 Thermodynamics 33 2.3.1 Free Copolymerization 34 2.3.2 Template-Directed Copolymerization 35 2.3.3 Depolymerization 35 2.4 Kinetics Yielding Bernoulli Chains 36 2.5 Kinetics Yielding Markov Chains 36 2.6 Kinetics Yielding Non-Markovian Chains 40 2.7 Effect of Sequence Disorder on Ceiling and Floor Temperatures 40 2.8 Mechanical Power of Sequence Disorder 43 2.9 Template-Directed Copolymerization 44 2.10 Conclusion 45 Acknowledgments 45 References 46 3 Nucleic Acid-Templated Synthesis of Sequence-Defined Synthetic Polymers 49Zhen Chen and David R. Liu 3.1 Introduction 49 3.2 Enzymatic Templated Syntheses of Non-Natural Nucleic Acids 50 3.2.1 Polymerase-Catalyzed Syntheses of Backbone-Modified Nucleic Acids 50 3.2.2 Polymerase-Catalyzed Syntheses of Nucleobase-Modified Nucleic Acids 52 3.2.3 Polymerase-Catalyzed Syntheses of Sugar-Modified Nucleic Acids 54 3.2.4 Ligase-Catalyzed Syntheses of Non-Natural Nucleic Acids 58 3.3 Ribosomal Synthesis of Non-Natural Peptides 59 3.4 Nonenzymatic Polymerization of Nucleic Acids 61 3.5 Nonenzymatic Polymerization of Non-Nucleic Acid Polymers 67 3.6 Conclusion and Outlook 71 Acknowledgments 73 References 73 4 Design of Sequence-Specific Polymers by Genetic Engineering 91Davoud Mozhdehi, Kelli M. Luginbuhl, Stefan Roberts, and Ashutosh Chilkoti 4.1 Introduction 91 4.2 Design of Repetitive Protein Polymers 93 4.3 Methods for the Genetic Synthesis of Repetitive Protein Polymers 96 4.4 Expression of Repetitive Protein Polymers 100 4.5 Expanding the Chemical Repertoire of Protein Polymers 100 4.5.1 Chemo-Enzymatic Modification 101 4.5.2 Incorporation of Noncanonical Amino Acids 104 4.5.3 Post-TranslationalModifications 105 4.6 Summary and Outlook 107 References 108 5 Peptide Synthesis and Beyond the Use of Sequence-Defined Segments for Materials Science 117Niels ten Brummelhuis, PatrickWilke, and Hans G. Börner 5.1 Introduction 117 5.2 The History of Solid-Phase-Supported Peptide Synthesis 118 5.3 Supports for the Chemical Synthesis of Peptides 120 5.4 Synthesis of Peptide–Polymer Conjugates 122 5.5 Identification of Functional Sequences 125 5.5.1 Phage Display 125 5.5.2 Split-and-Mix Libraries and SPOT Synthesis 130 5.5.3 Applications of Libraries 134 5.5.4 Dynamic Covalent (Pseudo)Peptide Libraries 136 5.6 Sequence–Property Relationships 136 5.7 Translation of Sequence to Synthetic Precision Polymer Platforms 137 5.8 Conclusion 141 References 141 6 Iterative SyntheticMethods for the Assembly of Sequence-Controlled Non-Natural Polymers 159Christopher Alabi 6.1 Introduction 159 6.2 The Solid-Phase Approach 161 6.2.1 Type of Solid Supports 161 6.2.2 Iterative Assembly using Single Heterobifunctional Monomers 162 6.2.3 Iterative Assembly usingMultiple HeterobifunctionalMonomers 163 6.3 The Liquid-Phase Approach 164 6.3.1 Requirements for Liquid-Phase Supports 165 6.3.2 Examples of Iterative Liquid-Phase Methodologies 165 6.3.3 The Fluorous Liquid-Phase Approach 167 6.4 The Template Approach 168 6.5 A Support-Free Approach 170 6.6 Outlook 175 References 176 7 Sequence-Controlled Peptoid Polymers: Bridging the Gap between Biology and Synthetic Polymers 183Mark A. Kline, Li Guo, and Ronald N. Zuckermann 7.1 Introduction 183 7.1.1 Closing the Gap between Biological Polymers and Synthetic Polymers 184 7.1.2 Enhancing Synthetic Polymers with Sequence Control 184 7.2 Peptoids – Bridging the Gap 187 7.3 Polypeptoid Synthesis 189 7.3.1 Solution Polymerization Method 189 7.3.2 Solid-Phase Synthesis Method 190 7.3.2.1 Solid-Phase Peptide Synthesis 190 7.3.2.2 Solid-Phase Peptoid Synthesis 192 7.3.2.3 Solid-Phase Submonomer Synthesis Method 192 7.3.3 Combinatorial Synthesis 197 7.3.4 Polypeptoid Analysis 197 7.4 Discovering Peptoid Properties Derived from Sequence Control 198 7.4.1 Peptoids as Potential Therapeutics 199 7.4.2 Peptoids with Controlled Conformation 199 7.4.2.1 Peptoid Properties Dominated by Side Chains 201 7.4.2.2 The Effect of Bulky Side Chains 201 7.4.2.3 The Peptoid Backbone Differs from a Peptide Backbone 202 7.4.2.4 Cyclic Peptoids 205 7.4.3 PeptoidsThat Function as Biomaterials 205 7.4.3.1 Antimicrobial and Antifouling Peptoids 206 7.4.3.2 Lipidated Peptoids for Drug Delivery 206 7.4.4 Ordered Supramolecular Assemblies: Toward Hierarchal Structures with Function 206 7.4.4.1 Supramolecular Self-Assembly from Uncharged Amphiphilic Diblock Copolypeptoids 207 7.4.4.2 Structures from Amphiphilic, Ionic-Aromatic Diblock Copolypeptoids 207 7.4.4.3 Free-Floating Two-Dimensional Peptoid Nanosheets with Crystalline Order 211 7.5 Conclusion 214 Acknowledgments 215 References 215 8 Sequence and Architectural Control in Glycopolymer Synthesis 229Yamin Abdouni, Gokhan Yilmaz, and C. Remzi Becer 8.1 Introduction: Glycopolymer–Lectin Binding 229 8.2 Sequence-Controlled Glycopolymers 230 8.2.1 Sequence-Defined Glycooligomers 231 8.2.2 Sequence Control via Time-Regulated Additions 234 8.2.3 Sequence Control via Time-Regulated Chain Extensions 235 8.2.4 Sequence Control via Orthogonal Reactions 237 8.3 Self-Assembly of Glycopolymers 238 8.3.1 Self-Assembly Based on Amphiphilicity 238 8.3.2 Temperature-Triggered Self-Assemblies 242 8.3.3 pH-Responsive Self-Assemblies 243 8.3.4 Self-Assembly Based on Electrostatic Interactions 245 8.4 Single-Chain Folding of Glycopolymers:The Future? 248 8.4.1 Selective Point Folding 249 8.4.2 Repeat Unit Folding 249 8.5 General Conclusion and Future Outlook 251 Acknowledgments 251 References 251 9 Sequence Regulation in Chain-Growth Polymerizations 257Makoto Ouchi 9.1 Introduction 257 9.2 Alternating Copolymerization 259 9.2.1 Addition Polymerization 259 9.2.2 Alternating ROMP 261 9.3 Iterative Single-Unit Addition with Living Polymerization 262 9.3.1 Iterative Process along with Purification via Peak Separation 263 9.3.2 Iterative Process along with Transformation of Pendant Group 266 9.4 Template-Assisted Polymerization 267 9.4.1 Template Initiator 268 9.4.2 Template Inimer 269 9.5 Cyclopolymerization 270 9.6 Ring-Opening Polymerization of Sequence-Programmed Monomer 272 9.7 Conclusion 274 References 274 10 Sequence-Controlled Polymers by Chain Polymerization 281Junpo He, Jie Ren, and ErlitaMastan 10.1 Introduction 281 10.2 Sequence-Controlled Polymers by Various Polymerization Mechanisms 282 10.2.1 Anionic Polymerization 282 10.2.2 Cationic Polymerization 289 10.2.3 Ring-Opening Polymerization (ROP) 290 10.2.4 Ring-Opening Metathesis Polymerization (ROMP) 292 10.2.4.1 Regioselective ROMP of Substituted Cyclooctene 292 10.2.4.2 Regioselective ROMP of Macrocyclic Compounds 294 10.2.4.3 Alternating Copolymerization 296 10.2.4.4 Kinetic Control for Polymers with Sequence-Defined Functionalities 299 10.2.5 Radical Polymerization 300 10.2.5.1 Polymers with Alternating AB Sequence 301 10.2.5.2 Polymer with ABB (1 : 2) Sequence 305 10.2.5.3 Polymers with Site-Specific Functionalization 307 10.2.5.4 Polymers with Precisely Controlled Sequence at Monomer Level 309 10.2.5.5 Other Sequence-Controlled Polymers 312 10.2.6 Coordination Polymerization 315 10.3 Concluding Remarks 316 References 317 11 Sequence-Controlled Polymers via Cationic Polymerization 327Sadahito Aoshima and Arihiro Kanazawa 11.1 Introduction 327 11.2 Recent Developments in Living Cationic Polymerization 328 11.2.1 Design of Initiating Systems for Living Polymerization 328 11.2.2 Base-Assisting Living Systems with Various Metal Halides 329 11.2.3 New Monomers for Cationic Polymerization 330 11.3 Sequence-Regulated Functional Polymers 331 11.3.1 Synthesis of New Block, Gradient, and End-Functionalized Polymers 331 11.3.2 Synthesis of Various Alternating Polymers by Controlled Cationic Polymerization 334 11.3.3 Synthesis of New Ring Polymers 336 11.4 Sequence Control Based on the Cationic Copolymerization of Vinyl and Cyclic Monomers 337 11.4.1 Strategy for Sequence Control by Copolymerizing Different Types of Monomers 337 11.4.2 Concurrent Cationic Vinyl-Addition and Ring-Opening Copolymerization of VEs and Oxiranes 338 11.4.3 Terpolymerization via the Exclusive One-way Cycle of Crossover Propagation Reactions 341 11.4.4 Concurrent Cationic Vinyl-Addition and Ring-Opening CopolymerizationMediated by Long-Lived Species 344 References 345 12 Periodic Copolymers by Step-Growth Polymerization 349Zi-Long Li and Zi-Chen Li 12.1 Introduction 349 12.2 Carbon-Chain Periodic Polymers 352 12.2.1 Acyclic Diene Metathesis Polymerization 352 12.2.2 Atom Transfer Radical Coupling 355 12.2.3 C(sp3)–C(sp3) Coupling 355 12.2.4 Atom Transfer Radical Polyaddition 356 12.3 Hetero-Chain Periodic Polymers 357 12.3.1 Polycondensation or Polyaddition of Oligomonomers 357 12.3.1.1 Polycondensation 357 12.3.1.2 Polyaddition via Click Reactions 359 12.3.1.3 Radical Addition–Coupling Polymerization 362 12.3.2 One-Pot SequentialMonomer Addition and Polymerization 364 12.3.3 Multicomponent Polymerizations 364 12.4 Conclusions and Outlook 369 References 372 13 Click and Click-Inspired Chemistry for the Design of Sequence-Controlled Polymers 379Steven Martens, Joshua O. Holloway, and Filip E. Du Prez 13.1 Introduction to “Click” and Click-Inspired ReactionsWithin the Area of Sequence-Controlled Polymers 379 13.2 Click and Click-Inspired Reactions for Sequence Building 380 13.2.1 Copper(I)-Catalyzed Azide/Alkyne Cycloaddition 380 13.2.2 Thiol–X and Thiolactone Chemistries 386 13.2.3 Diels–Alder: Photo-Triggered and Thermally Induced Reactions 395 13.3 Conclusions and Outlook 400 References 400 14 One-Pot Sequence-Controlled (SC) Multiblock Copolymers via Copper-Mediated Polymerization 417Athina Anastasaki, RichardWhitfield, Vasiliki Nikolaou, Nghia P. Truong, Glen R. Jones, Nikolaos G. Engelis, Evelina Liarou,Michael R.Whittaker, and David M. Haddleton 14.1 Introduction 417 14.2 Criteria for the Successful Synthesis of SC Multiblock Copolymers 419 14.3 Historical Background toward the Development of One-Pot SC Multiblocks 419 14.4 Access to SC Acrylic Multiblock Copolymers 420 14.4.1 The Cu(0)-Wire-Mediated RDRP Approach 420 14.4.1.1 When to Use Cu(0)-Wire-Mediated RDRP 422 14.4.1.2 When Not to UseThis Technique 422 14.4.1.3 Protocol for the Synthesis of Acrylic Multiblock Copolymers via Cu(0)-Wire-Mediated RDRP 423 14.4.2 Light-Mediated Copper Polymerization for the Synthesis of Acrylic Multiblock Copolymers 424 14.4.2.1 Attributes of the Light-Mediated Copper Polymerization Technique 426 14.4.2.2 Reasons Not to SelectThis Technique 426 14.4.2.3 Protocol for the Synthesis of Acrylic Multiblock Copolymers via Light-Mediated Copper Polymerization 426 14.5 Access to SC AcrylamideMultiblock Copolymers (The CuBr/Me6Tren Disproportionation Technique) 427 14.5.1 Why Use the CuBr/Me6Tren Disproportionation Technique 428 14.5.2 Reasons Not to SelectThis Technique 428 14.5.3 Protocol for the Synthesis of Acrylic Multiblock Copolymers via CuBr/Me6Tren Disproportionation Technique 429 14.6 Perspective and Outlook 429 References 430 15 Properties and Applications of Sequence-Controlled Polymers 435Jordan H. Swisher, Jamie A. Nowalk,Michael A.Washington, and Tara Y.Meyer 15.1 Introduction 435 15.1.1 Definitions 436 15.1.2 Types of Sequence-Dependent Properties 437 15.1.3 Categories of Sequence Comparison Studies 438 15.2 Molecular Properties 439 15.2.1 Monomer Order 439 15.2.2 Electronic/Vibrational Properties and Reactivity 439 15.3 Solution-Phase Properties 439 15.3.1 Folding 441 15.3.2 Recognition 443 15.3.3 Aggregation 444 15.4 Sequence Dependence of Bulk-Phase Properties 445 15.4.1 Category I – Block Composition 446 15.4.1.1 Block Dispersity 446 15.4.1.2 Block Frequency 446 15.4.2 Category II –Monomer Distribution 449 15.4.2.1 Tacticity 449 15.4.2.2 Alternating versus Random (and Block) 453 15.4.2.3 Gradient Copolymers 454 15.4.3 Category III – Precision Placement 454 15.4.4 Category IV– Side-Chain Sequence 458 15.4.5 Category V–Complex Sequences 458 15.5 Conclusions and Outlook 461 15.5.1 Solution-Phase Properties 462 15.5.2 Bulk-Phase Properties 464 15.5.3 The Future 466 References 466 16 Tandem Mass Spectrometry Sequencing of Sequence-Controlled and Sequence-Defined Synthetic Polymers 479Laurence Charles 16.1 Introduction 479 16.2 MS/MS Principle 480 16.3 MS/MS of Sequence-Controlled Copolymers 482 16.4 MS/MS of Sequence-Defined Polymers 485 16.4.1 Biomimetics 485 16.4.2 Sequence-Defined Copolymers for Information Storage 490 16.5 Conclusions and Perspectives 498 References 500 Index 505
Dr. Jean-Francois Lutz is CNRS research director, deputy director of the Institut Charles Sadron and head of the Precision Macromolecular Chemistry group in Strasbourg, France. He obtained his PhD from the University of Montpellier II, France, in 2000 and his habilitation degree from the University of Potsdam, Germany, in 2009. Before joining the CNRS, he subsequently was a post-doctoral fellow in the group of Krzysztof Matyjaszewski at Carnegie Mellon University, USA (2001-2003) and group leader Nanotechnology for Life Science at the Fraunhofer Institute for Applied Polymer Research in Potsdam (2003-2010). He received in 2008 the prize of the polymer division of the French Chemical Society. He is also an European Research Council (ERC) laureate since 2010 through successive starting (StG 2010) and proofs of concept (PoC 2015) grants. His current research interests include the synthesis of sequence-controlled polymers, single-chain technologies and the preparation of information-containing macromolecules. He is author of more than 150 publications.

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