Chemical Ligation

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

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 focus 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.