Chemical Ligation

Tools for Biomolecule Synthesis and Modification
Herausgegeben:D'Andrea, Luca D.; Romanelli, Alessandra

• Gebundenes Buch

Produktbeschreibung

Presenting a wide array of information on chemical ligation - one of the more powerful tools for protein and peptide synthesis - this book helps readers understand key methodologies and applications that protein therapeutic synthesis, drug discovery, and molecular imaging.

_ Moves from fundamental to applied aspects, so that novice readers can follow the entire book and apply these reactions in the lab
_ Presents a wide array of information on chemical ligation reactions, otherwise scattered across the literature, into one source
_ Features comprehensive and multidisciplinary coverage that goes from basics to advanced topics
_ Helps researchers choose the right chemical ligation technique for their needs

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Produktdetails

• Verlag: Wiley / Wiley & Sons
• Artikelnr. des Verlages: 1W119044100
• 1. Auflage
• Seitenzahl: 576
• Erscheinungstermin: 3. April 2017
• Englisch
• Abmessung: 239mm x 150mm x 36mm
• Gewicht: 953g
• ISBN-13: 9781119044109
• ISBN-10: 1119044103
• Artikelnr.: 47714462

Autorenporträt

Luca D. D'Andrea, PhD, is Research Scientist at the Institute of Biostructures and Bioimaging, CNR Naples, Italy. His scientific interests are in the field of peptide and protein chemistry. His research activity focuses on design, synthesis, and structural characterization of peptide/proteins as therapeutic/diagnostic agents. Alessandra Romanelli, PhD, is assistant professor of General Chemistry at Department of Pharmacy, University of Naples "Federico II", Italy. She actively works in the field of peptides and peptide-based molecules (such as peptide nucleic acids) as tools for chemical biology.

Inhaltsangabe

List of Figures xiii

List of Plates xxiii

List of Contributors xxix

Preface xxxiii

1 Introduction to Chemical Ligation Reactions 1
Lucia De Rosa, Alessandra Romanelli, and Luca Domenico D'Andrea

1.1 Introduction 1

1.2 Chemical Ligation Chemistries 6

1.3 Imine Ligations 7

1.4 Serine/Threonine Ligation (STL) 21

1.5 Thioether Ligation 24

1.6 Thioester Ligation 25

1.7 alpha?-Ketoacid?-Hydroxylamine (KAHA) Ligation 49

1.8 Staudinger Ligation 52

1.9 Azide-Alkyne Cycloaddition 57

1.10 Diels-Alder Ligation 61

References 64

2 Protein Chemical Synthesis by SEA Ligation 89
Oleg Melnyk, Claire Simonneau, and Jérôme Vicogne

2.1 Introduction 89

2.2 Essential Chemical Properties of SEA Group 93

2.3 Protein Total Synthesis Using SEA Chemistry - SEAon/off Concept 97

2.4 Chemical Synthesis of HGF/SF Subdomains for Deciphering the Functioning of HGF/SF-MET System 106

2.5 Conclusion 114

References 114

3 Development of Serine/Threonine Ligation and Its Applications 125
Tianlu Li and Xuechen Li

3.1 Introduction 125

3.2 Serine/Threonine Ligation (STL) 130

3.3 Application of STL in Protein Synthesis 140

3.4 Conclusion and Outlook 154

References 154

4 Synthesis of Proteins by Native Chemical Ligation-Desulfurization Strategies 161
Bhavesh Premdjee and Richard J. Payne

4.1 Introduction 161

4.2 Ligation-Desulfurization and Early Applications 162

4.3 Beyond Native Chemical Ligation at Cysteine - The Development of Thiolated Amino Acids and Their Application in Protein Synthesis 174

4.4 Ligation-Deselenization in the Chemical Synthesis of Proteins 211

4.5 Conclusions and Future Directions 216

References 218

5 Synthesis of Chemokines by Chemical Ligation 223
Nydia Panitz and Annette G. Beck?-Sickinger

5.1 Introduction - The Chemokine-Chemokine Receptor Multifunctional System 223

5.2 Synthesis of Chemokines by Native Chemical Ligation 224

5.3 Synthesis of Chemokines by Alternative Chemical Ligation 231

5.4 Semisynthesis of Chemokines by Expressed Protein Ligation 233

5.5 Prospects 241

References 243

6 Chemical Synthesis of Glycoproteins by the Thioester Method 251
Hironobu Hojo

6.1 Introduction 251

6.2 Ligation Methods and Strategy of Glycoprotein Synthesis 252

6.3 The Synthesis of the Extracellular Ig Domain of Emmprin 254

6.4 Synthesis of Basal Structure of MUC2 256

6.5 N?-Alkylcysteine?-Assisted Thioesterification Method and Dendrimer Synthesis 257

6.6 Synthesis of TIM?-3 260

6.7 Resynthesis of Emmprin Ig Domain 262

6.8 Conclusion 264

References 264

7 Membrane Proteins: Chemical Synthesis and Ligation 269
Marc Dittman and Martin Engelhard

7.1 Introduction 269

7.2 Methods for the Synthesis and Purification of Membrane Proteins 270

7.3 Ligation and Refolding 273

7.4 Illustrative Examples 276

References 280

8 Chemoselective Modification of Proteins 285
Xi Chen, Stephanie Voss, and Yao-Wen Wu

8.1 Chemical Protein Synthesis 285

8.2 Chemoselective and Bioorthogonal Reactions 287

8.3 Site-Selective Protein Modification Approaches 307

References 322

9 Stable, Versatile Conjugation Chemistries for Modifying Aldehyde-Containing Biomolecules 339
Aaron E. Albers, Penelope M. Drake and David Rabuka

9.1 Introduct