Chemical ligation : tools for biomolecule synthesis and modification

Description

Content: Cover Title Page Copyright Contents List of Figures List of Plates List of Contributors Preface Chapter 1 Introduction to Chemical Ligation Reactions 1.1 Introduction 1.1.1 Chemical Synthesis of Proteins: From the Stepwise Synthesis to the Chemical Ligation Approach 1.1.2 Chemical Modification of Proteins: From Conventional Methods to Chemoselective Labeling by Chemical Ligation 1.2 Chemical Ligation Chemistries 1.3 Imine Ligations 1.3.1 Oxime Ligation 1.3.2 Hydrazone Ligation 1.3.3 Pictet-Spengler Ligation 1.3.4 Thiazolidine Ligation 1.4 Serine/Threonine Ligation (STL) 2.3.2 SEAon/off Concept and the Design of a One-Pot Three Peptide Segment Assembly Process2.3.3 SEA on/off Concept and the Solid-Phase Synthesis of Proteins in the N-to-C Direction 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 3.1 Introduction 3.1.1 Protein Synthesis by SPPS 3.1.2 Native Chemical Ligation (and Extended Desulfurization) 3.1.3 KAHA Ligation 3.2 Serine/Threonine Ligation (STL) 3.2.1 SAL Ester Preparation 3.2.2 N-Terminal-Protecting Group for Successive C-to-N Ser/Thr Ligations3.2.3 Scope and Limitations 3.3 Application of STL in Protein Synthesis 3.3.1 Consecutive STL of Peptides/Proteins 3.3.2 STL-Mediated Peptide Cyclization 3.3.3 Thiol SAL Ester-Mediated Aminolysis in Peptide Cyclization 3.3.4 A Fluorogenic Probe for Recognizing 5-OH-Lys Inspired by STL 3.3.5 Expressed Protein Semisynthesis via Ser/Thr Ligation 3.4 Conclusion and Outlook References Chapter 4 Synthesis of Proteins by Native Chemical Ligation-Desulfurization Strategies 4.1 Introduction 4.2 Ligation-Desulfurization and Early Applications4.2.1 Metal‐Free Desulfurization 4.2.2 Ligation-Desulfurization toward the Synthesis of Proteins 4.3 Beyond Native Chemical Ligation at Cysteine - The Development of Thiolated Amino Acids and Their Application in Protein Synthesis 4.3.1 Phenylalanine 4.3.2 Valine 4.3.3 Lysine 4.3.4 Threonine 4.3.5 Leucine 4.3.6 Proline 4.3.7 Glutamine 4.3.8 Arginine 4.3.9 Aspartic Acid 4.3.10 Glutamic Acid 4.3.11 Tryptophan 4.3.12 GlcNAc-Asparagine 4.3.13 Asparagine 4.4 Ligation-Deselenization in the Chemical Synthesis of Proteins