Click chemistry for biotechnology and materials science

Title:

Publication Information:

Chichester, West Sussex : Wiley, 2009

Physical Description:

xvii, 411 p. : ill. (some col.) ; 26 cm.

ISBN:

9780470699706

Subject Term:

Biotechnology

Materials science

Combinatorial chemistry

Macromolecules -- Synthesis

Added Author:

Lahann, Joerg

Available:*

Library	Item Barcode	Call Number	Material Type	Item Category 1	Status
Searching... PSZ JB	30000010235261	TP248.2 L34 2009	Open Access Book	Book	Searching... Unknown

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 21st 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.

Author Notes

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.

Preface

List of Contributors

1 Click Chemistry A universal ligation strategy for Materials Science and BiotechnologyJoerg Lahann

1.1 Introduction

1.2 Selected examples of click reactions in materials science and biotechnology

1.3 Potential limitations of click chemistry

1.4 Conclusions

References

2 Common Synthons for Click Chemistry in BiotechnologyChristine Schilling and Nicole Jung and Stefan Bräse

2.1 Introduction - Click Chemistry

2.2 Peptides and derivatives

2.3 Peptoids

2.4 Peptidic dendrimers

2.5 Oligonucleotides

2.6 Carbohydrates

2.7 Conclusion

References

3 Copper-Free Click ChemistryJeremy M. Baskin and Carolyn R. Bertozzi

3.1 Introduction

3.2 Bio-orthogonal Ligations

3.3 Applications of Copper-Free Click Chemistries

3.4 Summary and Outlook

Acknowledgements

References

4 Protein and Peptide Conjugation to Polymers and Surfaces Using Oxime ChemistryHeather D. Maynard and Rebecca M. Broyer and Christopher M. Kolodziej

Introduction

4.2 Protein/Peptide-Polymer Conjugates

4.3 Immobilization of Proteins and Peptides on Surfaces

4.4 Conclusions

Acknowledgements

References

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

5.1 Introduction

5.2 Polymerization via CuAAC

5.3 Post-polymerization Modification via Click Chemistry

5.4 Polymer-Biomacromolecule Conjugation

5.5 Functional Nanomaterials

5.6 Summary and outlook

References

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

6.1 Introduction

6.2 Block Copolymers

6.3 Star Polymers

6.4 Graft Copolymers

6.5 Concluding Remarks

Abbreviations

References and Notes

7 "Click"-chemistry on supramolecular materialsWolfgang H. Binder and Robert Sachsenhofer

7.1 Introduction

7.2 "Click"-reactions on rotaxanes, cyclodextrines and macrocycles

7.3 "Click"-reactions on DNA

7.4 "Click"-reactions on supramolecular polymers

7.5 "Click"-reactions on membranes

7.6 "Click"-reactions on dendrimers

7.7 "Click"-reactions on gels and networks

7.8 "Click"-reactions on self-assembled monolayers

References

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

8.1 Introduction

8.2 Dendrimer Synthesis

8.3 Dendrimer Functionalization

8.4 Conclusions and Future Directions

References

9 Reversible Diels-Alder Cycloaddition for the Design of Multifunctional Network PolymersAmy M. Peterson and Giuseppe R. Palmese

9.1 Introduction

9.2 Design of Polymer Networks

9.3 Application of Diels-Alder Linkages to Polymer Systems

9.4 Conclusions

References

10 Click chemistry in the preparation of biohybrid materialsHeather J. Kitto and Jan Lauko and Floris P. J. T. Rutjes and Alan E. Rowan

10.1 Introduction

10.2 Polymer-containing biohybrid materials

10.3 Biohybrid structures based on protein conjugates

10.4 Biohybrid amphiphiles

10.5 Glycoconjugates

10.6 Conclusions

References

11 Functional Nanomaterials using the Cu-catalyzed Huisgen cycloaddition reactionSander S. van Berkel and Arnold W. G. Nijhuis and Dennis W. P.M. Löwik and Jan C. M. van Hest

11.1 Introduction

11.2 Inorganic nanoparticles

11.3 Carbon-based nanomaterials

11.4 Self assembled organic structures

11.5 Virus particles

11.6 Conclusions

Abbreviations

References

12 Copper-catalyzed "click" chemistry for surface engineeringHimabindu Nandivada and Joerg Lahann

12.1 Introduction

12.2 Synthesis of alkyne or azide functionalized surfaces

12.3 Spatially-controlled "click" chemistry

12.4 Copper-catalyzed "click" chemistry for bio-immobilization

Summary

References

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

13.1 Introduction

13.2 Post-translational Functionalization of Proteins with Azides and Alkynes

13.3 Co-translational Functionalization of Proteins with Azides and Alkynes

13.4 BONCAT: Identification of newly synthesized proteins via non-canonical amino acid tagging

13.5 Conclusions and Future Prospects

References

14 Fluorogenic copper(I)-catalyzed azide-alkyne cycloaddition reactions and their applications in bioconjugationCéline Le Droumaguet and Qian Wang

14.1 Click reaction for Bioconjugation Applications

14.2 Significance of Fluorogenic Reactions in Bioconjugation

14.3 CuAAC-Based Fluorogenic Reaction

14.4 Applications of CuAAC in Bioconjugation

14.5 Conclusions

References

15 Synthesis and Functionalization of Biomolecules via Click ChemistryChristine Schilling and Nicole Jung and Stefan Bräse

15.1 Introduction

15.2 Labeling of macromolecular biomolecules

15.3 Syntheses of natural products and derivatives

15.4 Enzymes and Click chemistry

15.5 Synthesis Glycosylated Molecular Architectures

15.6 Synthesis of nitrogen-rich compoundsPolyazides, and triazoles

15.7 Conclusions

References

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

16.1 Introduction

16.2 Diels-Alder "Click Chemistry" for Highly Efficient Side-Chain E-O Polymers

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

16.4 Diels-Alder "Click Chemistry" for NLO Dendrimers

16.5 Conclusions

Acknowledgements

References

Index

Available:*

On Order

Summary

Summary

Author Notes

Table of Contents