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Bioinspiration and Biomimicry in Chemistry
Reverse-Engineering Nature
Gerhard Swiegers (Edited by), G Swiegers (Author), Jean-Marie Lehn (Foreword by), Janine Benyus (Foreword by)
9780470566671, Wiley
Hardback, published 7 December 2012
512 pages
24 x 16.4 x 3.2 cm, 0.885 kg
“As a resource for chemists, the main advantage of this book is this diversity, which makes it stand out from more specific discussions of e.g. biomimetic materials chemistry. In this sense, the book would provide a good reference to someone new to the field or as part of a reading list for a course on biomimetics and bioinspiration in chemistry. In addition, for readers who have worked in one area of biomimetic chemistry for some time, this book is broad enough to give some interesting insight into some very different chemistries.” (Angew. Chem. Int. Ed, 1 August 2013) “As such, it holds a unique place in the literature, and would be best suited for advanced students or researchers interested in this area. Summing Up: Recommended. Graduate students, researchers/faculty, and professionals/practitioners.” (Choice, 1 August 2013)
Can we emulate nature's technology in chemistry? Through billions of years of evolution, Nature has generated some remarkable systems and substances that have made life on earth what it is today. Increasingly, scientists are seeking to mimic Nature's systems and processes in the lab in order to harness the power of Nature for the benefit of society. Bioinspiration and Biomimicry in Chemistry explores the chemistry of Nature and how we can replicate what Nature does in abiological settings. Specifically, the book focuses on wholly artificial, man-made systems that employ or are inspired by principles of Nature, but which do not use materials of biological origin. Beginning with a general overview of the concept of bioinspiration and biomimicry in chemistry, the book tackles such topics as: Written by a team of leading international experts, the contributed chapters collectively lay the groundwork for a new generation of environmentally friendly and sustainable materials, pharmaceuticals, and technologies. Readers will discover the latest advances in our ability to replicate natural systems and materials as well as the many impediments that remain, proving how much we still need to learn about how Nature works. Bioinspiration and Biomimicry in Chemistry is recommended for students and researchers in all realms of chemistry. Addressing how scientists are working to reverse engineer Nature in all areas of chemical research, the book is designed to stimulate new discussion and research in this exciting and promising field.
Foreword Foreword Preface xxiii Contributors xxv 1. Introduction: The Concept of Biomimicry and Bioinspiration in Chemistry 1 1.1 What is Biomimicry and Bioinspiration? 1 1.2 Why Seek Inspiration from, or Replicate Biology? 3 1.2.1 Biomimicry and Bioinspiration as a Means of Learning from Nature and Reverse-Engineering from Nature 3 1.2.2 Biomimicry and Bioinspiration as a Test of Our Understanding of Nature 4 1.2.3 Going Beyond Biomimicry and Bioinspiration 4 1.3 Other Monikers: Bioutilization, Bioextraction, Bioderivation, and Bionics 5 1.4 Biomimicry and Sustainability 5 1.5 Biomimicry and Nanostructure 7 1.6 Bioinspiration and Structural Hierarchies 9 1.7 Bioinspiration and Self-Assembly 11 1.8 Bioinspiration and Function 12 1.9 Future Perspectives: Drawing Inspiration from the Complex System that is Nature 13 References 14 2. Bioinspired Self-Assembly I: Self-Assembled Structures 17 2.1 Introduction 17 2.2 Molecular Clefts, Capsules, and Cages 19 2.2.1 Organic Cage Systems 21 2.2.2 Metallosupramolecular Cage Systems 24 2.3 Enzyme Mimics and Models: The Example of Carbonic Anhydrase 28 2.4 Self-Assembled Liposome-Like Systems 30 2.5 Ion Channel Mimics 32 2.6 Base-Pairing Structures 34 2.7 DNA–RNA Structures 36 2.8 Bioinspired Frameworks 38 2.9 Conclusion 41 References 41 3. Bioinspired Self-Assembly II: Principles of Cooperativity in Bioinspired Self-Assembling Systems 47 3.1 Introduction 47 3.2 Statistical Factors in Self-Assembly 48 3.3 Allosteric Cooperativity 50 3.4 Effective Molarity 52 3.5 Chelate Cooperativity 55 3.6 Interannular Cooperativity 60 3.7 Stability of an Assembly 62 3.8 Conclusion 67 References 67 4. Bioinspired Molecular Machines 71 4.1 Introduction 71 4.1.1 Inspirational Antecedents: Biology, Engineering, and Chemistry 72 4.1.2 Chemical Integration 75 4.1.3 Chapter Overview 77 4.2 Mechanical Effects in Biological Machines 78 4.2.1 Skeletal Muscle’s Structure and Function 78 4.2.2 Kinesin 79 4.2.3 F 1 -ATP Synthase 80 4.2.4 Common Features of Biological Machines 82 4.2.5 Variation in Biomotors 83 4.2.6 Descriptions and Analogies of Molecular Machines 83 4.3 Theoretical Considerations: Flashing Ratchets 83 4.4 Sliding Machines 86 4.4.1 Linear Machines: Rotaxanes 86 4.4.2 Mechanistic Insights: Ex Situ and In Situ (Maxwell’s Demon) 89 4.4.3 Bioinspiration in Rotaxanes 93 4.4.4 Molecular Muscles as Length Changes 93 4.5 Rotary Motors 102 4.5.1 Interlocked Rotary Machines: Catenanes 103 4.5.2 Unimolecular Rotating Machines 104 4.6 Moving Larger Scale Objects 104 4.7 Walking Machines 106 4.8 Ingenious Machines 109 4.8.1 Molecular Machines Inspired by Macroscopic Ones: Scissors and Elevators 109 4.8.2 Artificial Motility at the Nanoscale 109 4.8.3 Moving Molecules Across Surfaces 110 4.9 Using Synthetic Bioinspired Machines in Biology 111 4.10 Perspective 111 4.10.1 Lessons and Departures from Biological Molecular Machines 114 4.10.2 The Next Steps in Bioinspired Molecular Machinery 115 4.11 Conclusion 116 References 116 5. Bioinspired Materials Chemistry I: Organic–Inorganic Nanocomposites 121 5.1 Introduction 121 5.2 Silicate-Based Bionanocomposites as Bioinspired Systems 122 5.3 Bionanocomposite Foams 124 5.4 Biomimetic Membranes 126 5.4.1 Phospholipid–Clay Membranes 126 5.4.2 Polysaccharide–Clay Bionanocomposites as Support for Viruses 127 5.5 Hierarchically Layered Composites 129 5.5.1 Layer-by-Layer Assembly of Composite-Cell Model 129 5.5.2 Hierarchically Organized Nanocomposites for Sensor and Drug Delivery 130 5.6 Conclusion 133 References 134 6. Bioinspired Materials Chemistry II: Biomineralization as Inspiration for Materials Chemistry 139 6.1 Inspiration from Nature 139 6.2 Learning from Nature 144 6.3 Applying Lessons from Nature: Synthesis of Biomimetic and Bioinspired Materials 146 6.3.1 Biomimetic Bone Materials 147 6.3.2 Semiconductors, Nanoparticles, and Nanowires 151 6.3.3 Biomimetic Strategies for Silica-Based Materials 157 6.4 Conclusion 160 References 160 7. Bioinspired Catalysis 165 7.1 Introduction 165 7.2 A General Description of the Operation of Catalysts 168 7.3 A Brief History of Our Understanding of the Operation of Enzymes 169 7.3.1 Early Proposals: Lock-and-Key Theory, Strain Theory, and Induced Fit Theory 170 7.3.2 The Critical Role of Molecular Recognition in Enzymatic Catalysis: Pauling’s Concept of Transition State Complementarity 170 7.3.3 The Critical Role of Approach Trajectories in Enzymatic Catalysis: Orbital Steering, Near Attack Conformers, the Proximity Effect, and Entropy Traps 172 7.3.4 The Critical Role of Conformational Motion in Enzymatic Catalysis: Coupled Protein Motions 172 7.3.5 Enzymes as Molecular Machines: Dynamic Mechanical Devices and the Entatic State 173 7.3.6 The Fundamental Origin of Machine-like Actions: Mechanical Catalysis 174 7.4 Representative Studies of Bioinspired/Biomimetic Catalysts 177 7.4.1 Important General Characteristics of Enzymes as a Class of Catalyst 177 7.4.2 Bioinspired/Biomimetic Catalysts that Illustrate the Critical Importance of Reactant Approach Trajectories 178 7.4.3 Bioinspired/Biomimetic Catalysts that Demonstrate the Importance and Limitations of Molecular Recognition 182 7.4.4 Bioinspired/Biomimetic Catalysts that Operate Like a Mechanical Device 187 7.5 The Relationship Between Enzymatic Catalysis and Nonbiological Homogeneous and Heterogeneous Catalysis 192 7.6 Selected High-Performance NonBiological Catalysts that Exploit Nature’s Catalytic Principles 193 7.6.1 Adapting Model Species of Enzymes to Facilitate Machine-like Catalysis 194 7.6.2 Statistical Proximity Catalysts 201 7.7 Conclusion: The Prospects for Harnessing Nature’s Catalytic Principles 203 References 204 8. Biomimetic Amphiphiles and Vesicles 209 8.1 Introduction 209 8.2 Synthetic Amphiphiles as Building Blocks for Biomimetic Vesicles 210 8.3 Vesicle Fusion Induced by Molecular Recognition 216 8.4 Stimuli-Responsive Shape Control of Vesicles 224 8.5 Transmembrane Signaling and Chemical Nanoreactors 231 8.6 Toward Higher Complexity: Vesicles with Subcompartments 239 8.7 Conclusion 245 References 246 9. Bioinspired Surfaces I: Gecko-Foot Mimetic Adhesion 251 9.1 The Hierarchical Structure of Gecko Feet 251 9.2 Origin of Adhesion in Gecko Setae 252 9.3 Structural Requirements for Synthetic Dry Adhesives 253 9.4 Fabrication of Synthetic Dry Adhesives 254 9.4.1 Polymer-Based Dry Adhesives 254 9.4.2 Carbon-Nanotube-Based Dry Adhesives 278 9.5 Outlook 284 References 286 10. Bioinspired Surfaces II: Bioinspired Photonic Materials 293 10.1 Structural Color in Nature: From Phenomena to Origin 293 10.2 Bioinspired Photonic Materials 296 10.2.1 The Fabrication of Photonic Materials 297 10.2.2 The Design and Application of Photonic Materials 298 10.3 Conclusion and Outlook 317 References 319 11. Biomimetic Principles in Macromolecular Science 323 11.1 Introduction 323 11.2 Polymer Synthesis Versus Biopolymer Synthesis 325 11.2.1 Features of Polymer Synthesis 325 11.2.2 “Living” Chain Growth 326 11.2.3 Aspects of Chain Length Distribution in Synthetic Polymers: Sequence Specificity and Templating 328 11.3 Biomimetic Structural Features in Synthetic Polymers 330 11.3.1 Helically Organized Polymers 330 11.3.2 β-Sheets 333 11.3.3 Supramolecular Polymers 334 11.3.4 Self-Assembly of Block Copolymers 337 11.4 Movement in Polymers 343 11.4.1 Polymer Gels and Networks as Chemical Motors 343 11.4.2 Polymer Brushes and Lubrication 346 11.4.3 Shape-Memory Polymers 349 11.5 Antibody-Like Binding and Enzyme-Like Catalysis in Polymeric Networks 352 11.6 Self-Healing Polymers 355 References 362 12. Biomimetic Cavities and Bioinspired Receptors 367 12.1 Introduction 367 12.2 Mimics of the Michaelis–Menten Complexes of Zinc(II) Enzymes with Polyimidazolyl Calixarene-Based Ligands 368 12.2.1 A Bis-aqua Zn(II) Complex Modeling the Active Site of Carbonic Anhydrase 369 12.2.2 Structural Key Features of the Zn(II) Funnel Complexes 371 12.2.3 Hosting Properties of the Zn(II) Funnel Complexes: Highly Selective Receptors for Neutral Molecules 372 12.2.4 Induced Fit: Recognition Processes Benefit from Flexibility 373 12.2.5 Multipoint Recognition 374 12.2.6 Implementation of an Acid–Base Switch for Guest Binding 375 12.3 Combining a Hydrophobic Cavity and A Tren-Based Unit: Design of Tunable, Versatile, but Highly Selective Receptors 377 12.3.1 Tren-Based Calix[6]arene Receptors 377 12.3.2 Versatility of a Polyamine Site 378 12.3.3 Polyamido and Polyureido Sites for Synergistic Binding of Dipolar Molecules and Anions 380 12.3.4 Acid–Base Controllable Receptors 383 12.4 Self-Assembled Cavities 383 12.4.1 Receptors Decorated with a Triscationic or a Trisanionic Binding Site 384 12.4.2 Receptors Capped Through Assembly with a Tripodal Subunit 387 12.4.3 Heteroditopic Self-Assembled Receptors with Allosteric Response 388 12.4.4 Interlocked Self-Assembled Receptors 389 12.5 Conclusion 391 References 392 13. Bioinspired Dendritic Light-Harvesting Systems 397 13.1 Introduction 397 13.2 Dendrimer Architectures 399 13.2.1 Dendrimer as a Chromophore 399 13.2.2 Dendrimer as a Scaffold 401 13.3 Electronic Processes in Light-Harvesting Dendrimers 403 13.3.1 Energy Transfer in Dendrimers 403 13.3.2 Charge Transfer in Dendrimers 405 13.4 Light-Harvesting Dendrimers in Clean Energy Technologies 407 13.5 Conclusion 413 References 414 14. Biomimicry in Organic Synthesis 419 14.1 Introduction 419 14.2 Biomimetic Synthesis of Natural Products 420 14.2.1 Potentially Biomimetic Synthesis 423 14.3 Biomimetic Reactions in Organic Synthesis 437 14.4 Biomimetic Considerations as an Aid in Structural Assignment 447 14.5 Reflections on Biomimicry in Organic Synthesis 448 References 450 15. Conclusion and Future Perspectives: Drawing Inspiration from the Complex System that Is Nature 455 15.1 Introduction: Nature as a Complex System 455 15.2 Common Features of Complex Systems and the Aims of Systems Chemistry 457 15.3 Examples of Research in Systems Chemistry 460 15.3.1 Self-Replication, Amplification, and Feedback 460 15.3.2 Emergence, Evolution, and the Origin of Life 464 15.3.3 Autonomy and Autonomous Agents: Examples of Equilibrium and Nonequilibrium Systems 465 15.4 Conclusion: Systems Chemistry may have Implications in Other Fields 468 References 470 Index 473
Jean-Marie Lehn xvii
Janine Benyus xix
Timothy W. Hanks and Gerhard F. Swiegers
Leonard F. Lindoy, Christopher Richardson, and Jack K. Clegg
Gianfranco Ercolani and Luca Schiaffino
Christopher R. Benson, Andrew I. Share, and Amar H. Flood
Pilar Aranda, Francisco M. Fernandes, Bernd Wicklein, Eduardo Ruiz-Hitzky, Jonathan P. Hill, and Katsuhiko Ariga
Fabio Nudelman and Nico A. J. M. Sommerdijk
Gerhard F. Swiegers, Jun Chen, and Pawel Wagner
Sabine Himmelein and Bart Jan Ravoo
Liangti Qu, Yan Li, and Liming Dai
Cun Zhu and Zhong-Ze Gu
Wolfgang H. Binder, Marlen Schunack, Florian Herbst, and Bhanuprathap Pulamagatta
Stéphane Le Gac, Ivan Jabin, and Olivia Reinaud
Andrea M. Della Pelle and Sankaran Thayumanavan
Reinhard W. Hoffmann
Clyde W. Cady, David M. Robinson, Paul F. Smith, and Gerhard F. Swiegers
Subject Areas: Chemistry [PN]
