Chemical ligation : tools for biomolecule synthesis and modification / edited by Luca D. D'Andrea and Alessandra Romanelli.

Format:

Book

Contributor:

D'Andrea, Luca D., editor.

Romanelli, Alessandra, editor.

Language:

English

Subjects (All):

Biosynthesis.

Peptides--Synthesis.

Peptides.

Proteins--Synthesis.

Proteins.

Bioorganic chemistry.

Chemistry, Organic.

Physical Description:

1 online resource (583 pages) : illustrations (some color)

Edition:

1st ed.

Place of Publication:

Hoboken, New Jersey : Wiley, 2017.

Summary:

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

Contents:

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)

1.5 Thioether Ligation

1.6 Thioester Ligation

1.6.1 Native Chemical Ligation (NCL)

1.6.2 Expressed Protein Ligation (EPL)

1.6.3 Thioacid-Mediated Ligation Strategies

1.7 α-Ketoacid-Hydroxylamine (KAHA) Ligation

1.7.1 Acyltrifluoroborates and Hydroxylamines Ligation

1.8 Staudinger Ligation

1.9 Azide-Alkyne Cycloaddition

1.10 Diels-Alder Ligation

References

Chapter 2 Protein Chemical Synthesis by SEA Ligation

2.1 Introduction

2.2 Essential Chemical Properties of SEA Group

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

2.3.1 Synthesis of SEAoff Peptide Segments

2.3.2 SEAon/off Concept and the Design of a One-Pot Three Peptide Segment Assembly Process

2.3.3 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

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 Ligations

3.2.3 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

Chapter 4 Synthesis of Proteins by Native Chemical Ligation-Desulfurization Strategies

4.1 Introduction

4.2 Ligation-Desulfurization and Early Applications

4.2.1 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

4.4.1 Selenol Amino Acids

4.5 Conclusions and Future Directions

Chapter 5 Synthesis of Chemokines by Chemical Ligation

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

Chapter 6 Chemical Synthesis of Glycoproteins by the Thioester Method

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

Chapter 7 Membrane Proteins: Chemical Synthesis and Ligation

7.1 Introduction

7.2 Methods for the Synthesis and Purification of Membrane Proteins

7.2.1 Synthesis of Hydrophobic Peptides

7.2.2 Purification of Hydrophobic Peptides

7.3 Ligation and Refolding

7.3.1 Ligation Strategies

7.3.2 Refolding of Chemically Synthesized Hydrophobic Peptides and Membrane Proteins

7.4 Illustrative Examples

7.4.1 Diacylglycerol Kinase (DAGK)

7.4.2 Semisynthesis of the Sensory Rhodopsin/Transducer Complex

7.4.3 Semisynthesis of the Functional K+ Channel KcsA

Chapter 8 Chemoselective Modification of Proteins

8.1 Chemical Protein Synthesis

8.1.1 Native Chemical Ligation (NCL) and Expressed Protein Ligation (EPL)

8.1.2 Traceless Staudinger Ligation

8.2 Chemoselective and Bioorthogonal Reactions

8.2.1 Oxime/Hydrazone Ligation

8.2.2 Staudinger Ligations

8.2.3 Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC)

8.2.4 Strain-Promoted Azide-Alkyne Cycloaddition (SPAAC)

8.2.5 Inverse Electron-Demand Diels-Alder Cycloaddition (DAINV)

8.2.6 Light-Induced Click Reactions

8.2.7 1,2-Aminothiol Condensation

8.2.8 Transition-Metal-Catalyzed Couplings

8.2.9 Miscellaneous Protein-Labeling Reactions

8.3 Site-Selective Protein Modification Approaches

8.3.1 Site-Selective Modification of Native Proteins

8.3.2 Chemical Tags for Labeling Proteins in Live Cells

8.3.3 Unnatural Amino Acid Mutagenesis

Chapter 9 Stable, Versatile Conjugation Chemistries for Modifying Aldehyde-Containing Biomolecules

9.1 Introduction.

9.2 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

Chapter 10 Thioamide Labeling of Proteins through a Combination of Semisynthetic Methods

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

10.5.1 Structural Studies

10.5.2 Use as Photoswitches

10.5.3 Site-Specific Circular Dichroism Labels

10.5.4 Fluorescence Quenching

10.5.5 Protein Folding in Model Systems

10.5.6 Monitoring Proteolysis

10.5.7 α-Synuclein Misfolding Studies

10.6 Conclusions

Acknowledgments

Chapter 11 Macrocyclic Organo-Peptide Hybrids by Intein-Mediated Ligation: Synthesis and Applications

11.1 Introduction

11.1.1 Naturally Occurring Macrocyclic Peptides

11.1.2 Natural Product Analogs via Reengineering of NRPS and PRPS Biosynthetic Pathways

11.2 Macrocyclic Organo-Peptide Hybrids as Natural-Product-Inspired Macrocycles

11.2.1 MOrPHs via CuAAC/Hydrazide-Mediated Ligation

11.2.2 Catalyst-Free MOrPH Synthesis via Oxime/AMA-Mediated Ligation

11.2.3 Structure-Reactivity Relationships in MOrPH Synthesis

11.2.4 Synthesis of MOrPH Libraries

11.2.5 Macrocyclization Mech

11.2.6 Bicyclic Organo-Peptide Hybrids

11.3 Application of MOrPHs for Targeting α-Helix-Mediated Protein-Protein Interactions

11.4 Conclusions

Chapter 12 Protein Ligation by HINT Domains.

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 Intramolecular 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

Acknowledgment

Chapter 13 Chemical Ligation for Molecular Imaging

13.1 Introduction

13.2 Chemical Ligation

13.2.1 Classical Chemical Ligation

13.2.2 Bioorthogonal Chemistry

13.3 Conclusion

Chapter 14 Native Chemical Ligation in Structural Biology

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

Index

Supplemental Images

EULA.

Notes:

Incudes bibliographical references at the end of each chapters and index.

Description based on print version record.

ISBN:

9781119044130

1119044138

9781119044093

111904409X

9781119044116

1119044111

OCLC:

962750333