Protection of Functional Groups in Peptide Synthesis

List of Contributors

Preface

Nomenclature and Abbreviations

Contents of Previous Volumes

Chapter 1 Amine Protecting Groups

I Introduction

II Amine Protection

III The Types of Amine Protecting Groups

IV Selective Protection of α, ω-Diaminocarboxylic Acids

V Amide Protecting Groups

VI Hydrazide Protection

VII Guanidine Protecting Groups

VIII Imidazole Protecting Groups

IX Npyr-Protection of β-(3-Pyrazolyl)alanine

X Indole Protecting Groups

XI Concluding Remarks

References

Chapter 2 Carboxyl Protecting Groups

I Introduction

II Synthesis without Protection of Carboxyl Groups

III Trimethylsilyl Esters

IV Protecting Groups Cleaved by Mild Acid Treatment

V Protecting Groups Cleaved by Hydrogenolysis

VI Protecting Groups Removed by Treatment with Alkali

VII Protecting Groups Cleaved by Nucleophiles under Neutral Conditions

VIII Protecting Groups Cleaved by Photolysis

IX Methods of Preparing Amino Acid Esters

X Concluding Remarks

References

Chapter 3 Sulfhydryl Group Protection in Peptide Synthesis

I Introduction

II Thioethers and Related Protective Groups

III Monothioacetals, Dithioacetals, and Related Protective Groups

IV Thiazolidines and Related Protective Groups

V Thioesters and Related Derivatives

VI Sulfenyl Derivatives (Preparation and Removal)

References

Chapter 4 Protection of the Hydroxyl Group in Peptide Synthesis

I Introduction

II Synthetic Strategy for Hydroxyl-Containing Peptides: "Minimal" versus "Global" Protection

III Serine in Peptide Synthesis

IV Threonine in Peptide Synthesis

V Hydroxyproline in Peptide Synthesis

VI Other Aliphatic Hydroxy Acids: Depsipeptides

VII Tyrosine in Peptide Synthesis

VIII Peptide Synthesis with Other Phenolic Amino Acids

IX Optical Purity of Peptides and Amino Acids

References

Chapter 5 Differential Protection and Selective Deprotection in Peptide Synthesis

I Introduction

II General Methods for the Cleavage of Protecting Groups

III Deprotection by Acidolysis

IV Alkali-Labile Protecting Groups

V Compatibility of Protecting Groups

VI Differential Protection

References

Chapter 6 Peptide Synthesis with Minimal Protection of Side-Chain Functions

I Introduction

II Tactics and Problems Connected with Use of Minimal Side-Chain Protection

III Strategies and Examples of Syntheses with Minimal Side-Chain Protection

IV Concluding Remarks

References

Chapter 7 Dual Function Groups

I Substituted Hydrazides

II Esters

III Miscellaneous Groups

References

Author Index

Subject Index