Chemoselective and Bioorthogonal Ligation

This timely, one-stop reference is the first on an emerging and interdisciplinary topic. Covering both established and recently developed ligation chemistries, the book is divided into two didactic parts: a section that focuses on the details of bioorthogonal and chemoselective ligation reactions at the level of fundamental organic chemistry, and a section that focuses on applications, particularly in the areas of chemical biology, biomaterials, and bioanalysis, highlighting the capabilities and benefits of the ligation reactions. With chapters authored by outstanding scientists who range from trailblazers in the field to young and emerging leaders, this book on a highly interdisciplinary topic will be of great interest for biochemists, biologists, materials scientists, pharmaceutical chemists, organic chemists, and many others.

Igor L. Medintz is the U.S. Navy's Senior Scientist for Biosensors and Biomaterials at the U.S. Naval Research Laboratory in Washington, D.C. He obtained his Ph.D. from the City University of New York and then spent three years as a postdoctoral researcher at the University of California, Berkeley. He has coauthored over 200 scientific publications, 18 patents, and won several awards including the 2013 Arthur S. Flemming Award for Basic Science.

W. Russ Algar is an Assistant Professor at the University of British Columbia in Vancouver, Canada, and a Canada Research Chair (Tier 2) and Michael Smith Foundation for Health Research Scholar. He obtained his Ph.D. from the University of Toronto, and then spent two years as a postdoctoral researcher at the U.S. Naval Research Laboratory in Washington, D.C., USA. He has authored over 70 scientific publications and won several awards and fellowships for his research.

Philip Dawson obtained his Ph.D. under the guidance of Prof. Kent. After two years postdoctoral research at Caltech under Prof. H. Gray he became Associate Professor at the Scripps Research Institute in La Jolla, USA. His research field is synthetic protein chemistry. He has published more than 100 papers in international journals and has won several awards (Max Bergmann medal, Vincent du Vigneaud Award of the American Peptide Society).

Contents to Volume 1

List of Contributors xi

Preface xvii

Part I Chemistries 1

1 A Brief Introduction to Traditional Bioconjugate Chemisrty 3
W. Russ Algar

2 (3+2)-Doplar Cycloadditions in Bioconjugation 37
Jason E. Hein

3 Diels-Adler and Inverse Diels-Adler Reactions 67
Roberto J. Brea and Neal K. Devaraj

4 The Straudinger Ligation 97
Olaia Nieto-Garcia, Marcie B. Jaffee, Michaela Muhlberg, and Christian P.R. Hackenberger

5 Thiol-Ene Chemistry 117
Neil B. Cramer and Christopher N. Bowman

6 Ligand-Directed Tosyl and Acyl Imidazole Chemisrty 147
Kazuya Matsuo and Itaru Hamachi

7 Bioorthogonal Labeling of Cellular Proteins by Enzymatic and Related Mechanisms 165
Scott A. Walper, Kendrick B. Turner, and Igor L. Medintz

8 Metal-Mediated Bioconjugation 231
Justin M. Chalker

Contents to Volume 2

List of Contributors xiii

Preface xix

Part II applications 271

9 Protein and Anitbody Labeling 273
Angela M. Mariani and Kim E. Sapsford

10 Activity-Based Protein Profiling 305
Elaine V. Wolf and Steven H.L. Verhelst

11 Nucleic Acid Labeling, Ligation and Modicfication 335
Afah H. El-Sagheer and Tom Brown

12 Chemoselective Reactions for Glycan Labeling 363
Janet E. McCombs and Jennifer J. Kholer

13 Chemoselective Attachment of Lipids to Proteins 391
Christian F. W. Becker

14 In Vivo Applications of Bioorthogonal Chemistries 417
Chelsea G. Gordon and Carolyn R. Bertozzi

15 Immobilization of Biomolecular Probes for Arrays and Assays: Critical Aspects of Biointerfaces 459
Stella H. North and Chris Rowe Taitt

16 Chemical Ligations in the Design of Hydrogel Materials 497
Scott H. Medina and Joel P. Schneider

17 Nanoparticle Bioconjugates: Materials that Benefit from Chemoselective and Bioorthogonal Ligation Chemistires 543
Melissa Massey and W. Russ Algar

18 Applications of Engineered Viral Nanoparticles in Materials and Medicine 631
Michael D. Glidden II, John F. Edelbrock, Amy M. Wen, Sourabh Shukla, Yingfang Ma, Roger H. French, Jonathan K. Pokorski, and Nicole F. Steinmetz

Index 711

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Chemoselective and Bioorthogonal Ligation Reactions Concepts and Applications

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