Major Methods of Peptide Bond Formation

List of Contributors

Preface

Nomenclature and Abbreviations

Chapter 1 The Peptide Bond

I Introduction

II Nature of the Peptide Bond

III Cleavage of the Peptide Bond

IV Formation of the Peptide Bond

V Conclusion and Outlook

References

Chapter 2 The Formation of Peptide Bonds: A General Survey

I Introduction

II Coupling between Amino Acid Residues

III Ab Initio Assembly of the Backbone

IV Conclusions

References

Chapter 3 Active Esters in Peptide Synthesis

I The Development of Active Esters

II Classes of Active Esters

III Preparation of Active Esters

IV Catalysis of Active Ester Reactions

V Side Reactions

VI Active Esters and the Strategy of Peptide Synthesis

VII Active Esters in Various Techniques of Peptide Synthesis

VIII Conclusions

References

Chapter 4 The Azide Method in Peptide Synthesis

I Introduction

II Experimental Procedure

III The Formation of Hydrazides

IV The Generation of Azides

V Azide Segment Condensation

VI Special Applications

VII Opportunities and Constraints

References

Chapter 5 The Carbodiimide Method

I Introduction

II Mechanism of Carboxyl Activation

III Reaction Conditions for Dicyclohexyl-Carbodiimide-Mediated Peptide Bond Formation

IV Reactions of Carbodiimides with Amines

References

Chapter 6 The Mixed Carbonic Anhydride Method of Peptide Synthesis

I Introduction

II The Experimental Procedure

III Reaction Conditions

IV Coupling Reagents: EEDQ and IIDQ

V Applications

VI Related Methods

VII Opportunities and Constraints

References

Chapter 7 Racemization in Peptide Synthesis

I Introduction

II Racemization of Amino Acids, Peptides, and Their Unactivated Derivatives

III Racemization of Activated Acyl Derivatives of Amino Acids and Peptides

IV Control of Racemization during Peptide Synthesis

V Strategies for Minimizing Racemization During Amide-Forming Steps

VI Assays for Chiral Purity

References

Author Index

Subject Index