Chemical LigationTools for Biomolecule Synthesis and Modification
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
Preface List of Contributors Chapter 1: Introduction to chemical ligation reactions Lucia De Rosa, Alessandra Romanelli, Luca D. D’Andrea 1.1 Introduction 1.2 Chemical ligation chemistries 1.3 Imine ligations 1.4 Serine/Threonine ligation (STL) 1.5 Thioether ligation 1.6 Thioester ligation 1.7 ?-ketoacid-hydroxylamine (KAHA) ligation 1.8 Staudinger ligation 1.9 Azide-Alkyne cycloaddition 1.10 Diels-Alder ligation References Chapter 2: Protein chemical synthesis by SEA ligation Oleg Melnyk, Claire Simonneau, Jérôme Vicogne 2.1 Introduction 2.2 Essential chemical properties of SEA group 2.3 Protein total synthesis using SEA chemistry. SEA on/off concept 2.4 Chemical synthesis of HGF/SF subdomains for deciphering the functioning of HGF/SF-MET system 2.5 Conclusion References Chapter 3: Development of Serine/Threonine ligation and its applications Tianlu Li, Xuechen Li 3.1 Introduction 3.2 Serine/Threonine Ligation (STL) 3.3 Application of STL in protein synthesis 3.4 Conclusion and Outlook References Chapter 4: Synthesis of Proteins by Native Chemical Ligation-Desulfurization Strategies Bhavesh Premdjee and Richard J. Payne 4.1 Introduction 4.2 Ligation-desulfurization and early applications 4.3 Beyond native chemical ligation at cysteine - the development of thiolated amino acids and their application in protein synthesis 4.4 Ligation-deselenization in the chemical synthesis of proteins 4.5 Conclusions and future directions References Chapter 5: Synthesis of Chemokines by Chemical Ligation Nydia Panitz and Annette G. Beck-Sickinger 5.1 Introduction – the chemokine-chemokine receptor multifunctional system 5.2 Synthesis of Chemokines by Native Chemical Ligation 5.3 Synthesis of chemokines by alternative chemical ligation 5.4 Semisynthesis of Chemokines by Expressed Protein Ligation 5.5 Prospects References Chapter 6: Chemical Synthesis of Glycoproteins by the Thioester Method Hironobu Hojo 6.1 Introduction 6.2 Ligation methods and strategy of glycoprotein synthesis 6.3 The synthesis of the extracellular Ig domain of emmprin 6.4 Synthesis of basal structure of MUC2 6.5 N-alkylcysteine-assisted thioesterification method and dendrimer synthesis 6.6 Synthesis of TIM-3 6.7 Resynthesis of emmprin Ig domain 6.8 Conclusion References Chapter 7: Membrane Proteins: Chemical Synthesis and Ligation Marc Dittman and Martin Engelhard 7.1 Introduction 7.2 Methods for the synthesis and purification of membrane proteins 7.3 Ligation and Refolding 7.4 Illustrative examples References Chapter 8: Chemoselective modification of proteins Xi Chen, Stephanie Voss, Yao-Wen Wu 8.1 Chemical protein synthesis 8.2 Chemoselective and bioorthogonal reactions 8.3 Site-selective protein modification approaches References Chapter 9: Stable, versatile conjugation chemistries for modifying aldehyde-containing biomolecules Aaron E. Albers, Penelope M. Drake, and David Rabuka 9.1 Introduction 9.2 The aldehyde as a bioorthogonal chemical handle for conjugation 9.3 Aldehyde conjugation chemistries 9.4 The Pictet-Spengler ligation 9.5 The Hydrazinyl Iso-Pictet-Spengler (HIPS) ligation 9.6 The trapped Knoevenagel (thioPz) ligation 9.7 Applications—Antibody-drug conjugates 9.8 Next-generation HIPS chemistry—AzaHIPS 9.9 Applications—Protein engineering 9.10 Applications—Protein labeling 9.11 Conclusions References Chapter 10: Thioamide Labeling of Proteins Through a Combination of Semi-synthetic Methods Christopher R. Walters, John J. Ferrie, and E. James Petersson 10.1 Introduction 10.2 Thioamide Synthesis 10.3 Thioamide Incorporation into Peptides 10.4 Synthesis of Full-Sized Proteins Containing Thioamides 10.5 Applications 10.6. Conclusions Acknowledgments References Chapter 11: Macrocyclic Organo-Peptide Hybrids by Intein-mediated Ligation: Synthesis and Applications John R. Frost and Rudi Fasan 11.1 Introduction 11.2 Macrocyclic Organo-Peptide Hybrids as natural product-inspired macrocycles 11.3 Application of MOrPHs for targeting??-helix-mediated protein-protein interactions. 11.4 Conclusions References Chapter 12: Protein ligation by HINT domains Hideo Iwaï and A. Sesilja Aranko 12.1 Introduction 12.2 Protein ligation by protein splicing 12.3 Naturally occurring and artificially split inteins for protein ligation 12.4 Conditional protein splicing 12.5 Inter- and intra-molecular protein splicing 12.6 Protein ligation by other HINT domains 12.7 Bottleneck of protein ligation by PTS 12.8 Comparison with other enzymatic ligation methods 12.9 Perspective of protein ligation by HINT domains 12.10 Conclusions and future perspectives Acknowledgments References Chapter 13: Chemical ligation for molecular imaging Aurélien Godinat, Hacer Karatas, Ghyslain Budin, Elena A. Dubikovskaya 13.1 Introduction 13.2 Chemical ligation 13.3 Conclusion References Chapter 14: Native Chemical Ligation in Structural Biology Lucia De Rosa, Alessandra Romanelli, Luca D. D’Andrea 14.1 Introduction 14.2 Protein (semi)synthesis for molecular structure determination 14.3 Protein (semi)synthesis for understanding protein folding, stability and interactions 14.4 Protein (semi)synthesis in enzyme chemistry References Index
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.
Chemical biology deals with the use and development of chemical tools to solve biological problems, and chemical ligation fits within this paradigm as a set of techniques used for creating long peptide or protein chains. The practices involved represent a powerful enhancement of traditional solid-phase peptide synthesis – allowing the chemical preparation of proteins, biomolecule synthesis, protein labeling or immobilization, and preparation of proteins with unnatural amino acids. These molecular tools are useful for understanding biological systems and preparing novel bio- and nanomaterials or synthetizing bioactive molecules. Until recently restricted to use by specialized scientists, chemical ligation methods are now in widespread use across interdisciplinary research groups and to different scientific areas. There is a clear need for a single-source resource and reference about these techniques and that is where Chemical Ligation: Tools for Biomolecule Synthesis and Modification comes in. Presenting a wide array of information on chemical ligation, this book guides readers between different chemical ligation methodologies and applications – from the basics to more recent and sophisticated applications. The chapters move from the fundamental to applied aspects, so that novice readers can follow the entire book and apply these reactions in the laboratory. The authors reserve attention for synthetic aspects, so the book also serves as a valuable reference for experimental work. Additionally, a selection of outstanding applications – including protein therapeutic synthesis, drug discovery, and molecular imaging – provides an overview of chemical ligation's potential and get other scientists involved bringing new ideas and applications.