Cover -- Title Page -- Copyright -- Contents -- Preface -- Abbreviations -- Part I The Basics of Peptidomimetics -- Chapter 1 The Basics of Peptidomimetics -- 1.1 Introduction -- 1.2 Definition and Classification -- 1.3 Strategic Approaches to Peptidomimetic Design -- 1.3.1 Modification of Amino Acids -- 1.3.2 Compounds with Global Restrictions -- 1.3.3 Molecular Scaffolds Mimicking the Peptidic Backbone -- 1.4 Successful Examples of Peptidomimetic Drugs -- 1.4.1 ACE Inhibitors -- 1.4.2 Thrombin Inhibitors -- 1.5 Conclusion -- References -- Chapter 2 Synthetic Approaches towards Peptidomimetic Design -- 2.1 Introduction -- 2.2 Local Modifications -- 2.2.1 Single Amino Acid Modifications -- 2.2.2 Dipeptide Isosteres -- 2.2.3 Retro-inverso Peptides -- 2.2.4 N-Methylation of Peptides -- 2.2.5 Azapeptides -- 2.2.6 Peptoids -- 2.3 Global Restrictions through Cyclic Peptidomimetics -- 2.4 Peptidomimetic Scaffolds -- 2.5 Conclusions -- References -- Part II Synthetic Methods and Molecules -- Chapter 3 Peptidomimetic Bioisosteres -- 3.1 Introduction -- 3.2 Peptide Bond Isosteres -- 3.2.1 Thioamides -- 3.2.2 Esters -- 3.2.3 Alkenes and Fluoroalkenes -- 3.2.4 Transition-State Isosteres -- 3.3 Side-Chain Isosteres -- 3.3.1 Guanidine Isosteres in Arginine Peptidomimetics -- 3.3.2 Isosteres of Aspartic Acid and Glutamic Acid -- 3.3.3 Tethered α-Amino Acids: Constraining the x-Space -- 3.4 Dipeptide Isosteres -- 3.4.1 δ-Amino Acids -- 3.5 Tripeptide Isosteres -- 3.6 Conclusion -- References -- Chapter 4 Solid-Phase Synthesis and Combinatorial Approaches to Peptidomimetics -- 4.1 Introduction -- 4.2 Solid-Phase Synthesis of Peptidomimetics -- 4.2.1 Scaffolds from α-Amino Acids -- 4.2.2 Scaffolds from Amino Aldehyde Intermediates -- 4.2.3 Pyrrolidine-Containing Scaffolds -- 4.3 Conclusion -- References.

Chapter 5 Click Chemistry: The Triazole Ring as a Privileged Peptidomimetic Scaffold -- 5.1 Introduction -- 5.1.1 CuAAC Reaction -- 5.1.2 Triazole Ring as a Peptidomimetic Isostere -- 5.2 Triazole-Containing Peptidomimetics Elaborated through `Click Chemistry' -- 5.2.1 Macrocycles -- 5.2.2 Oligomers and Foldamers -- 5.3 Relevant Applications in Drug Discovery -- 5.3.1 AChE Inhibitors -- 5.3.2 HIV Protease Inhibitors -- 5.3.3 MMP Inhibitors -- 5.3.4 Integrin Ligands -- 5.4 Conclusions -- Acknowledgements -- References -- Chapter 6 Peptoids -- 6.1 Introduction and Basics of Peptoids -- 6.2 Synthetic Methods -- 6.3 Macrocyclic Peptoids -- 6.4 Conformational Analysis of Folded Peptoids -- 6.5 Application of Peptoids as Antimicrobial Peptidomimetics -- 6.6 Conclusions -- References -- Chapter 7 Sugar Amino Acids -- 7.1 Introduction -- 7.2 α-SAAs -- 7.2.1 Furanoid α-SAAs -- 7.2.2 Pyranoid α-SAAs -- 7.3 β-SAAs -- 7.3.1 Furanoid β-SAAs -- 7.3.2 Pyranoid β-SAAs -- 7.4 r-SAAs1 -- 7.5 δ-SAAs -- 7.5.1 Furanoid δ-SAAs -- 7.5.2 Pyranoid δ-SAAs -- 7.6 Representative Applications in Medicinal Chemistry -- 7.7 Conclusions -- References -- Chapter 8 Cyclic α-Amino Acids as Proline Mimetics -- 8.1 Introduction -- 8.2 Cyclic α-Amino Acids -- 8.2.1 3-Substituted Proline Derivatives -- 8.2.2 4-Substituted Proline Derivatives -- 8.2.3 5-Substituted Proline Derivatives -- 8.2.4 Other Heterocyclic Proline Analogues -- 8.3 Bicyclic αAmino Acids -- 8.3.1 β/r-Ring Junction -- 8.3.2 α/r-Ring Junction -- 8.3.3 r/δ-Ring Junction -- 8.3.4 α/δ-Ring Junction -- 8.3.5 β/δ-Ring Junction -- 8.3.6 N/β-Ring Junction -- 8.3.7 Pipecolic-Based Bicyclic α-Amino Acids -- 8.3.8 Morpholine-Based Bicyclic α-Amino Acids -- 8.4 Conclusions -- References -- Chapter 9 β-Turn Peptidomimetics -- 9.1 Introduction -- 9.2 Definition and Classification of β-Turns.

9.3 Conformational Analysis -- 9.4 β-Turn Peptidomimetics -- 9.4.1 Proline Analogues in β-Turn Peptidomimetics -- 9.4.2 δ-Amino Acids as Reverse-Turn Inducers -- 9.4.3 Molecular Scaffolds as β-Turn Peptidomimetics -- 9.5 Conclusions -- References -- Chapter 10 Peptidomimetic Foldamers -- 10.1 Introduction -- 10.2 Classification -- 10.3 Peptoids -- 10.4 β-Peptides: First Systematic Conformational Studies -- 10.5 Hybrid Foldamers -- 10.6 From Structural to Functional Foldamers -- 10.6.1 Peptoids as Foldameric Antimicrobial Peptidomimetics -- 10.6.2 Foldamers Targeting Bcl-xL Antiapoptotic Proteins -- 10.7 Conclusions -- References -- Part III Applications in Medicinal Chemistry -- Chapter 11 Case Study 1: Peptidomimetic HIV Protease Inhibitors -- 11.1 Introduction -- 11.2 The HIV-1 Virus -- 11.2.1 HIV-1 Protease -- 11.3 Antiretroviral Therapy -- 11.4 Drug Resistance -- 11.4.1 Mechanisms of Resistance to Protease Inhibitors -- 11.5 HIV-1 Protease Inhibitors -- 11.5.1 Transition-State Analogues -- 11.5.2 Peptidomimetic Drugs -- 11.5.3 Next-Generation Cyclic Peptidomimetic Inhibitors -- 11.6 Conclusions -- Acknowledgements -- References -- Chapter 12 Case Study 2: Peptidomimetic Ligands for αvβ3 Integrin -- 12.1 Introduction -- 12.2 Peptide-Based Peptidomimetic Integrin Ligands -- 12.3 Scaffold-Based Peptidomimetic Integrin Ligands -- 12.4 Conclusions -- References -- Index -- Supplemental Images.