Introduction to Peptide Science

Preface vii

1 Basic Properties 1

1.1 Introduction 1

1.2 Properties of Amino Acids 2

1.3 The Peptide Bond 22

1.4 Secondary Structures 24

1.5 Peptide Structure and Conformation Characterization Methods 32

1.6 Peptide Databases and Web Software 39

Bibliography 43

2 Synthesis 45

2.1 Introduction 45

2.2 Solid-Phase Peptide Synthesis 46

2.3 Solution-Phase Peptide Synthesis 58

2.4 Methods to Prepare Longer Peptides 59

2.5 Peptide Library Synthesis 62

2.6 Synthesis of Cyclic Peptides 65

2.7 Peptidomimetics 69

2.8 Post-Translational Modifications 70

2.9 Lipidation 71

2.10 Glycosylation 73

2.11 Polypeptide Polymers and Conjugates of Peptides and Polymers 74

2.12 Non-Ribosomal Peptide Synthesis 80

2.13 Purification and Analysis Methods 80

Bibliography 84

3 Amyloid and Other Peptide Aggregate Structures 87

3.1 Introduction 87

3.2 Amyloid 90

3.3 Amyloid ß 93

3.4 Mechanisms and Kinetics of Amyloid Aggregation 100

3.5 Toxicity and Relevance to Disease 105

3.6 Fibrillization of Small Peptides 108

3.7 Biological Functional Amyloid and Bioengineering Applications of Amyloid Materials 110

3.8 Fibrils From a-Helices 111

3.9 Peptide Hydrogels and Tissue Scaffolds 112

3.10 Peptide Nanotubes 116

3.11 Peptide and Peptide Conjugate Assemblies 119

3.12 Characterization Methods for Peptide Assemblies 124

Bibliography 130

4 Antimicrobial and Cell-penetrating Peptides 133

4.1 Introduction 133

4.2 Bacterial Pathogens, Targets of Antibacterial Agents, and Antimicrobial Resistance Pathways 134

4.3 Testing Antimicrobial Activity 139

4.4 Bacterial Biofilms 140

4.5 Design of Antimicrobial Peptides 144

4.6 Classes of Antibacterial Peptides 146

4.7 Antifungal Peptides 155

4.8 Antiviral Peptides 159

4.9 Antiparasitic Peptides 160

4.10 Mechanisms of Activity 160

4.11 Cell-Penetrating Peptides 164

Bibliography 167

5 Peptide Hormones and Peptide Therapeutics 169

5.1 Introduction 169

5.2 General Principles of Peptide Therapeutics 170

5.3 Peptide Hormones 176

5.4 Neuropeptides and other Peptides In vivo 202

5.5 Venom-Derived Peptides 204

5.6 Anticancer Peptides 207

5.7 Miscellaneous Peptide Therapeutics 212

5.8 Cosmetic Peptides and Lipopeptides 214

Bibliography 216

Index 219