Protection of Functional Groups in Peptide Synthesis

Protection of Functional Groups in Peptide Synthesis

The Peptides Analysis, Synthesis, Biology, Vol. 3

1st Edition - January 1, 1981

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  • Editors: Erhard Gross, Johannes Meienhofer
  • eBook ISBN: 9781483217987

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The Peptides: Analysis, Synthesis, Biology, Volume 3: Protection of Functional Groups in Peptide Synthesis focuses on protection of functional groups in peptide synthesis. This book consists of seven chapters. Chapter 1 reviews the large variety of amine protecting groups. The protection of carboxyl groups is described in Chapter 2, while the chemistry of sulfhydryl group protection in peptide synthesis is discussed in Chapter 3. Chapter 4 covers the protection of the hydroxyl groups of serine, threonine, tyrosine, and other hydroxyl-containing amino acids. Differential protection and selective deprotection in peptide synthesis is deliberated in Chapter 5. In chapter 6, the opportunities and constraints of the tactics of minimal protection of side-chain functions during peptide synthesis are reviewed. The last chapter is devoted to the interesting aspects of dual function groups. This volume is recommended for specialists and researchers concerned with peptide and protein research.

Table of Contents

  • List of Contributors


    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


    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


    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)


    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


    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


    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


    Chapter 7 Dual Function Groups

    I Substituted Hydrazides

    II Esters

    III Miscellaneous Groups


    Author Index

    Subject Index

Product details

  • No. of pages: 400
  • Language: English
  • Copyright: © Academic Press 1981
  • Published: January 1, 1981
  • Imprint: Academic Press
  • eBook ISBN: 9781483217987

About the Editors

Erhard Gross

Johannes Meienhofer

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