Click Chemistry for Biotechnology and Materials Science / Edition 1

by Joerg Lahann

Overview

Mimicking natural biochemical processes, click chemistry is a modular approach to organic synthesis, joining together small chemical units quickly, efficiently and predictably. In contrast to complex traditional synthesis, click reactions offer high selectivity and yields, near-perfect reliability and exceptional tolerance towards a wide range of functional groups and reaction conditions. These ‘spring loaded’ reactions are achieved by using a high thermodynamic driving force, and are attracting tremendous attention throughout the chemical community. Originally introduced with the focus on drug discovery, the concept has been successfully applied to materials science, polymer chemistry and biotechnology.

The first book to consider this topic, Click Chemistry for Biotechnology and Materials Science examines the fundamentals of click chemistry, its application to the precise design and synthesis of macromolecules, and its numerous applications in materials science and biotechnology.  The book surveys the current research, discusses emerging trends and future applications, and provides an important nucleation point for research.

Edited by one of the top 100 young innovators with the greatest potential to have an impact on technology in the 21^st century according to Technology Review and with contributions from pioneers in the field, Click Chemistry for Biotechnology and Materials Science provides an ideal reference for anyone wanting to learn more about click reactions.

Product Details

ISBN-13:	9780470699706
Publisher:	Wiley
Publication date:	11/23/2009
Pages:	432
Product dimensions:	6.80(w) x 9.90(h) x 1.00(d)

About the Author

Joerg Lahann is Dow Corning Assistant Professor in the Chemical Engineering Department at the University of Michigan (USA). He was educated at the University of Saarland (Germany) and obtained his PhD at RWTH Aachen (Germany) in Macromolecular Chemistry. From 1999 to 2001, Joerg Lahann was a postdoctoral associate in the Chemical Engineering Department of Massachusetts Institute of Technology (USA) and he then spent one year at Harvard University and Massachusetts Institute of Technology (HMST). He joined the Chemical Engineering Department at the University of Michigan in 2003. Professor Lahann has received a number of honors and awards including Technology Review TR100 Young Innovator Award, NSF CAREER Award, the Justus-Liebig Fellowship of the Fonds of the German Industry, Sigma XI - Full Membership, German Science Foundation Postdoctoral Grant, Borchers Prize of the RWTH Aachen (given to graduate students for an outstanding performance), and the Young Student Achievement Award of the Fonds of the German Industry. His research interests are broadly related to surface engineering as well as biomedical engineering and nanotechnology.

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Table of Contents

Preface xiii

List of Contributors xv

Acknowledgments xix

1 Click Chemistry: A Universal Ligation Strategy for Biotechnology and Materials Science 1
Joerg Lahann

1.1 Introduction 1

1.2 Selected Examples of Click Reactions in Materials Science and Biotechnology 2

1.3 Potential Limitations of Click Chemistry 5

1.4 Conclusions 5

References 6

2 Common Synthons for Click Chemistry in Biotechnology 9
Christine Schilling, Nicole Jung and Stefan Bräse

2.1 Introduction – Click Chemistry 9

2.2 Peptides and Derivatives 10

2.3 Peptoids 12

2.4 Peptidic Dendrimers 13

2.5 Oligonucleotides 14

2.6 Carbohydrates 18

2.7 Conclusion 25

References 26

3 Copper-free Click Chemistry 29
Jeremy M. Baskin and Carolyn R. Bertozzi

3.1 Introduction 29

3.2 Bio-orthogonal Ligations 30

3.2.1 Condensations of Ketones and Aldehydes with Heteroatom-bound Amines 31

3.2.2 Staudinger Ligation of Phosphines and Azides 32

3.2.3 Copper-free Azide–Alkyne Cycloadditions 35

3.2.4 Bioorthogonal Ligations of Alkenes 37

3.3 Applications of Copper-free Click Chemistries 38

3.3.1 Activity-based Profiling of Enzymes 38

3.3.2 Site-specific Labeling of Proteins 39

3.3.3 Metabolic Labeling of Glycans 41

3.3.4 Metabolic Targeting of Other Biomolecules with Chemical Reporters 44

3.4 Summary and Outlook 45

References 46

4 Protein and Peptide Conjugation to Polymers and Surfaces Using Oxime Chemistry 53
Heather D. Maynard, Rebecca M. Broyer and Christopher M. Kolodziej

4.1 Introduction 53

4.2 Protein/Peptide–Polymer Conjugates 54

4.3 Immobilization of Proteins and Peptides on Surfaces 60

4.4 Conclusions 66

References 67

5 The Role of Click Chemistry in Polymer Synthesis 69
Jean-François Lutz and Brent S. Sumerlin

5.1 Introduction 69

5.2 Polymerization via CuAAC 70

5.3 Post-polymerization Modification via Click Chemistry 72

5.4 Polymer–Biomacromolecule Conjugation 76

5.5 Functional Nanomaterials 81

5.6 Summary and Outlook 83

References 85

6 Blocks, Stars and Combs: Complex Macromolecular Architecture Polymers via Click Chemistry 89
Sebastian Sinnwell, Andrew J. Inglis, Martina H. Stenzel and Christopher Barner-Kowollik

6.1 Introduction 89

6.2 Block Copolymers 91

6.2.1 Preparing Polymers for Click Conjugations 92

6.2.2 The Click Reaction: Methodologies and Isolation 96

6.2.3 Polymer Characterization 99

6.3 Star Polymers 101

6.3.1 Star polymers A_n 101

6.3.2 Dentritic Star Polymers 107

6.4 Graft Copolymers 107

6.4.1 ‘Grafting-to’ Azide Main Chains 109

6.4.2 ‘Grafting-to’ Alkyne Main Chains 111

6.4.3 Non-CuAAC Routes 113

6.5 Concluding Remarks 113

References 113

7 Click Chemistry on Supramolecular Materials 119
Wolfgang H. Binder and Robert Sachsenhofer

7.1 Introduction 119

7.2 Click Reactions on Rotaxanes, Cyclodextrines and Macrocycles 123

7.2.1 Click with Rotaxanes 123

7.2.2 Click on Cyclodextrines 126

7.2.3 Click on Macrocycles 128

7.3 Click Reactions on DNA 131

7.4 Click Reactions on Supramolecular Polymers 138

7.5 Click Reactions on Membranes 143

7.6 Click Reactions on Dendrimers 147

7.7 Click Reactions on Gels and Networks 147

7.8 Click Reactions on Self-assembled Monolayers 153

References 164

8 Dendrimer Synthesis and Functionalization by Click Chemistry for Biomedical Applications 177
Daniel Q. McNerny, Douglas G. Mullen, Istvan J. Majoros, Mark M. Banaszak Holl and James R. Baker Jr

8.1 Introduction 177

8.2 Dendrimer Synthesis 181

8.2.1 Divergent Synthesis 181

8.2.2 Convergent Synthesis 183

8.3 Dendrimer Functionalization 184

8.4 Conclusions and Future Directions 189

References 191

9 Reversible Diels–Alder Cycloaddition for the Design of Multifunctional Network Polymers 195
Amy M. Peterson and Giuseppe R. Palmese

9.1 Introduction 195

9.2 Design of Polymer Networks 198

9.3 Application of Diels–Alder Linkages to Polymer Systems 199

9.3.1 Molecular Weight Control of Linear Polymers 200

9.3.2 Remoldable Crosslinked Materials 202

9.3.3 Thermally Removable Encapsulants 203

9.3.4 Reversibly Crosslinked Polymer–Solvent Gels 203

9.3.5 Remendable Materials 204

9.3.6 Recyclable Thermosets 206

9.3.7 Smart Materials 207

9.4 Conclusions 209

References 209

10 Click Chemistry in the Preparation of Biohybrid Materials 217
Heather J. Kitto, Jan Lauko, Floris P. J. T. Rutjes and Alan E. Rowan

10.1 Introduction 217

10.2 Polymer-containing Biohybrid Materials 218

10.2.1 Polymers from Controlled Techniques 218

10.2.2 Bio-inspired Polymers via Click Chemistry 220

10.3 Biohybrid Structures based on Protein Conjugates 228

10.4 Biohybrid Amphiphiles 232

10.5 Glycoconjugates 236

10.5.1 Carbohydrate Clusters 236

10.5.2 Glycopeptides 238

10.5.3 Glycopolymers 244

10.6 Conclusions 247

References 247

11 Functional Nanomaterials using the Cu-catalyzed Huisgen Cycloaddition Reaction 255
Sander S. van Berkel, Arnold W.G. Nijhuis, Dennis W.P.M. Löwik and Jan C.M. van Hest

11.1 Introduction 255

11.2 Inorganic Nanoparticles 256

11.2.1 Silicon-based Nanoparticles 256

11.2.2 Cadmium Selenide-based Nanoparticles 257

11.2.3 Ferric Oxide-based Nanoparticles 257

11.2.4 Gold-based Nanoparticles 261

11.3 Carbon-based Nanomaterials 266

11.3.1 Fullerenes 267

11.3.2 Carbon Nanotubes 269

11.4 Self-assembled Organic Structures 272

11.4.1 Liposomes 274

11.4.2 Polymersomes 275

11.4.3 Micelles and Cross-linked Nanoparticles 278

11.5 Virus Particles 281

11.6 Conclusions 284

References 285

12 Copper-catalyzed ‘Click’ Chemistry for Surface Engineering 291
Himabindu Nandivada and Joerg Lahann

12.1 Introduction 291

12.2 Synthesis of Alkyne or Azide-functionalized Surfaces 292

12.2.1 Self-assembled Monolayers of Alkanethiolates 292

12.2.2 Self-assembled Monolayers of Silanes and Siloxanes 292

12.2.3 Block Copolymers 294

12.2.4 Layer-by-layer Films 296

12.2.5 Chemical Vapor Deposition Polymerization 297

12.2.6 Fiber Networks 298

12.3 Spatially Controlled Click Chemistry 299

12.4 Copper-catalyzed Click Chemistry for Bioimmobilization 300

12.5 Summary 305

References 305

13 Click Chemistry in Protein Engineering, Design, Detection and Profiling 309
Daniela C. Dieterich and A. James Link

13.1 Introduction 309

13.2 Posttranslational Functionalization of Proteins with Azides and Alkynes 310

13.3 Cotranslational Functionalization of Proteins with Azides and Alkynes 314

13.4 BONCAT: Identification of Newly Synthesized Proteins via Noncanonical Amino Acid Tagging 318

13.5 Conclusions and Future Prospects 321

References 322

14 Fluorogenic Copper(I)-catalyzed Azide–Alkyne Cycloaddition Reactions Reactions and their Applications in Bioconjugation 327
Céline Le Droumaguet and Qian Wang

14.1 Click Reaction for Bioconjugation Applications 327

14.2 Significance of Fluorogenic Reactions in Bioconjugation 328

14.3 CuAAC-based Fluorogenic Reaction 332

14.4 Applications of CuAAC in Bioconjugation 337

14.4.1 Fluorogenic Probing of Cellular Components 339

14.4.2 Fluorogenic Conjugation of DNA 341

14.4.3 Fluorogenic Conjugation of Viruses 344

14.4.4 Fluorogenic Conjugation of Nanoparticles/Polymers 345

14.5 Conclusions 348

References 349

15 Synthesis and Functionalization of Biomolecules via Click Chemistry 355
Christine Schilling, Nicole Jung and Stefan Bräse

15.1 Introduction 355

15.2 Labeling of Macromolecular Biomolecules 356

15.2.1 Fluorescent Labeling 356

15.2.2 Labeling of Bovine Serum Albumin 360

15.2.3 Biotin-labeling of Biomolecules: ABPP 361

15.2.4 Fluorine Labeling 364

15.3 Syntheses of Natural Products and Derivatives 365

15.4 Enzymes and Click Chemistry 368

15.5 Synthesis of Glycosylated Molecular Architectures 371

15.6 Synthesis of Nitrogen-rich Compounds: Polyazides and Triazoles 373

15.7 Conclusions 374

References 375

16 Unprecedented Electro-optic Properties in Polymers and Dendrimers Enabled by Click Chemistry Based on the Diels–Alder Reactions 379
Jingdong Luo, Tae-Dong Kim and Alex K.-Y. Jen

16.1 Introduction 379

16.2 Diels–Alder Click Chemistry for Highly Efficient Side-chain E-O Polymers 380

16.3 Diels–Alder Click Chemistry for Crosslinkable E-O Polymers Containing Binary NLO Chromophores 388

16.4 Diels–Alder Click Chemistry for NLO Dendrimers 392

16.5 Conclusions 394

References 397

Index 399

What People are Saying About This

From the Publisher

"This book is a high-quality reference for people working in the field or for people interested in using click chemistry in biotechnology and/or materials science." (Angewandte Chemie, 2010)

"This book should remain an essential reference source for many years." (Chemistry World, April 2010)

Editorial Reviews

"This book is a high-quality reference for people working in the field or for people interested in using click chemistry in biotechnology and/or materials science." (Angewandte Chemie, 2010)

 

"This book should remain an essential reference source for many years." (Chemistry World, April 2010)

From the Publisher