| Description |
1 online resource (652 pages) |
| Contents |
Title Page ; Copyright Page; Contents; Foreword; Introduction; About the Contributors; Part I Challenges Specific to Macrocycles; Chapter 1 Contemporary Macrocyclization Technologies; 1.1 Introduction; 1.2 Challenges Inherent to the Synthesis of Macrocycles; 1.3 Challenges in Macrocycle Characterization; 1.4 Macrocyclization Methods; 1.5 Cyclization on the Solid Phase; 1.6 Summary; References; Chapter 2 A Practical Guide to Structural Aspects of Macrocycles (NMR, X-Ray, and Modeling) ; 2.1 Background; 2.1.1 Classes of Macrocycles Covered |
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2.1.2 Applications of Macrocycles in Drug Design and Agriculture and the Role of Structural Information in These Applications2.1.3 Experimental Techniques (NMR and X-Ray) ; 2.1.4 Modeling Studies; 2.2 Experimental Studies of Macrocycles; 2.2.1 NMR Experiments and Parameters That Yield Structural Information; 2.2.2 Protocols for 3D Structural Determination Using NMR; 2.2.3 Dynamic Aspects of Structures (NMR Relaxation); 2.2.4 X-Ray Studies of Macrocycles ; 2.2.5 Macrocycle-Receptor Interactions (NMR and X-Ray) ; 2.3 Molecular Modeling of Macrocyclic Peptides |
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2.3.1 Methods and Challenges in Modeling Cyclic Peptides2.3.1.1 Quantum Mechanics; 2.3.1.2 Molecular Mechanics; 2.3.2 Conformation, Dynamics, and Electrostatics of Cyclic Peptides; 2.3.2.1 NMR Spectroscopy Combined with MD Simulations; 2.3.2.2 Studying Large Conformational Ensembles and Folding; 2.3.2.3 Electrostatic Characteristics of Cyclic Peptides; 2.3.3 Modeling the Activity of Cyclic Peptides; 2.3.3.1 Cyclic Peptide Interactions with Molecular Targets; 2.3.3.2 Cyclic Peptide Nanotubes; 2.3.3.3 Membrane Permeation and Diffusion; 2.3.4 Engineering Cyclic Peptides as Grafting Scaffolds |
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2.4 SummaryAcknowledgments; References; Chapter 3 Designing Orally Bioavailable Peptide and Peptoid Macrocycles ; 3.1 Introduction; 3.2 Improving Peptide Plasma Half-Life ; 3.3 Absorption, Bioavailability, and Methods for Predicting Absorption; 3.3.1 In Vitro Assays; 3.3.2 Paracellular Absorption; 3.3.3 Tight Junction Modifiers to Improve Paracellular Absorption; 3.3.4 Transcellular Absorption of Macrocycles; 3.3.4.1 Cyclization; 3.3.4.2 N-Methylation ; 3.3.4.3 Cyclosporine A (CSA); 3.3.4.4 Conformational Interconversion and H-Bond Networks ; 3.3.4.5 Shielding |
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3.3.4.6 Additional Strategies for Managing Hydrogen Bond Donors3.4 In Silico Modeling; 3.5 Future Directions; References; Part II Classes of Macrocycles and Their Potential for Drug Discovery; Chapter 4 Natural and Nature-Inspired Macrocycles: A Chemoinformatic Overview and Relevant Examples ; 4.1 Introduction to Natural Macrocycles as Drugs and Drug Leads; 4.2 Biosynthetic Pathways, Natural Role, and Biotechnological Access; 4.3 QSAR and Chemoinformatic Analyses of Common Features; 4.4 Case Studies: Selected Natural Macrocycles of Special Relevance in Medicinal Chemistry; References |
| Notes |
Chapter 5 Bioactive and Membrane-Permeable Cyclic Peptide Natural Products |
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Print version record |
| Subject |
Drug development.
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Pharmaceutical chemistry.
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Chemistry, Pharmaceutical
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Drug development
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Pharmaceutical chemistry
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| Form |
Electronic book
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| Author |
Peterson, Mark L
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| ISBN |
9781119092582 |
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1119092582 |
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