{"product_id":"chiral-separations-and-stereochemical-elucidation-9781119802259","title":"Chiral Separations and Stereochemical Elucidation","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003e\u003cp\u003e\u003cb\u003eAn expert resource for chemists using stereochemical analysis methods\u003c\/b\u003e \u003c\/p\u003e\u003cp\u003eIn \u003ci\u003eChiral Separations and Stereochemical Elucidation: Fundamentals, Methods, and Applications\u003c\/i\u003e, a team of distinguished researchers delivers a robust and authoritative discussion of the theoretical fundamentals of chiral separation, the most commonly used chiral selectors, and stereochemical elucidation methods. The book offers expert discussions of a variety of chiral separation methods by gas chromatography (GC), supercritical fluid chromatography (SFC), capillary electrophoresis (CE), and liquid chromatography (LC). \u003c\/p\u003e\u003cp\u003eThe authors also describe several methods for stereochemical elucidation, including X-ray crystallography, nuclear magnetic resonance spectroscopy, and chiroptical methods. The explored material is ideal for practicing chemists seeking a resource to help them guide method development and optimization or to explain quality control-complements during target compound production. \u003c\/p\u003e\u003cp\u003eR\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003c\/p\u003e\u003cp\u003eList of Contributors xv\u003c\/p\u003e \u003cp\u003ePreface xix\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart I Fundamentals of Chiral Separation 1\u003cbr\u003e\u003cbr\u003e 1 Chiral Separation by LC 3\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eJuliana Cristina Barreiro and Quezia Bezerra Cass\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e1.1 Introduction 3\u003c\/p\u003e \u003cp\u003e1.2 Workflow for LC Chiral Method Development 7\u003c\/p\u003e \u003cp\u003e1.3 New Column Technologies 9\u003c\/p\u003e \u003cp\u003e1.4 Selected Examples of Fast Separation 12\u003c\/p\u003e \u003cp\u003e1.5 Chiral 2D- LC 14\u003c\/p\u003e \u003cp\u003e1.5.1 LC–LC and mLC–LC 14\u003c\/p\u003e \u003cp\u003e1.5.2 LC × LC and sLC × LC 17\u003c\/p\u003e \u003cp\u003e1.6 Future and Perspectives 19\u003c\/p\u003e \u003cp\u003eReferences 20\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Chiral Separation by GC 27\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eOliver Trapp\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e2.1 Introduction 27\u003c\/p\u003e \u003cp\u003e2.2 Chiral Recognition in Gas Chromatography 29\u003c\/p\u003e \u003cp\u003e2.2.1 Chiral Recognition by Hydrogen Bonding 31\u003c\/p\u003e \u003cp\u003e2.2.2 Chiral Recognition Using Chiral Metal Complexes 31\u003c\/p\u003e \u003cp\u003e2.2.3 Chiral Recognition by Host–Guest Interactions 31\u003c\/p\u003e \u003cp\u003e2.3 Preparation of Fused- Silica Capillaries for GC with CSPs 33\u003c\/p\u003e \u003cp\u003e2.4 Application of CSPs in Chiral Gas Chromatography 34\u003c\/p\u003e \u003cp\u003e2.4.1 CSPs with Diamide Selectors 34\u003c\/p\u003e \u003cp\u003e2.4.1.1 Chirasil- Val 34\u003c\/p\u003e \u003cp\u003e2.4.2 CSPs with CD Selectors 35\u003c\/p\u003e \u003cp\u003e2.4.2.1 Heptakis(2,3,6- tri- O- Methyl)- β- Cyclodextrin (Permethyl- β- Cyclodextrin) 38\u003c\/p\u003e \u003cp\u003e2.4.2.2 Heptakis(2,3,6- tri- O- Methyl)- β- Cyclodextrin Immobilized to Hydrido Dimethyl Polysiloxane (Chirasil- β- Dex) 39\u003c\/p\u003e \u003cp\u003e2.4.2.3 Heptakis(2,6- di- O- Methyl- 3- O- Pentyl)- β- Cyclodextrin 43\u003c\/p\u003e \u003cp\u003e2.4.2.4 Hexakis- (2,3,6-tri- O- Pentyl)- α- Cyclodextrin 47\u003c\/p\u003e \u003cp\u003e2.4.2.5 Heptakis(2,3,6- tri- O- Pentyl)- β- Cyclodextrin 48\u003c\/p\u003e \u003cp\u003e2.4.2.6 Hexakis- (3- O- Acetyl- 2,6- di- O- Pentyl)- α- Cyclodextrin 51\u003c\/p\u003e \u003cp\u003e2.4.2.7 Heptakis(3- O- Acetyl- 2,6- di- O- Pentyl)- β- Cyclodextrin 51\u003c\/p\u003e \u003cp\u003e2.4.2.8 Octakis(3- O- Butyryl- 2,6- di- O- Pentyl)- γ- Cyclodextrin 53\u003c\/p\u003e \u003cp\u003e2.4.2.9 Hexakis\/Heptakis\/Octakis(2,6- di- O- Alkyl- 3- O- Trifluoroacetyl)- α\/β\/γ- Cyclodextrins 57\u003c\/p\u003e \u003cp\u003e2.4.2.10 Heptakis(2,3- di- O- Acetyl- 6- O-tert- Butyldimethylsilyl)- β- Cyclodextrin (DIAC- 6- TBDMS- β- CD) 58\u003c\/p\u003e \u003cp\u003e2.4.2.11 Heptakis(2,3- di- O- Methyl- 6- O-tert- Butyldimethylsilyl)- β- Cyclodextrin (DIME- 6- TBDMS- β- CD) 58\u003c\/p\u003e \u003cp\u003e2.4.3 Cyclofructans 62\u003c\/p\u003e \u003cp\u003e2.4.4 CSPs with Metal Complexes 65\u003c\/p\u003e \u003cp\u003e2.5 Conclusion 69\u003c\/p\u003e \u003cp\u003eReferences 69\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Chiral Separation by Supercritical Fluid Chromatography 85\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eEmmanuelle Lipka\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e3.1 Introduction 85\u003c\/p\u003e \u003cp\u003e3.2 Characteristics and Properties of Supercritical Fluids 87\u003c\/p\u003e \u003cp\u003e3.3 Development of a Chiral SFC Method 89\u003c\/p\u003e \u003cp\u003e3.3.1 Chiral Stationary Phases 89\u003c\/p\u003e \u003cp\u003e3.3.2 Mobile Phases 91\u003c\/p\u003e \u003cp\u003e3.3.2.1 Mobile Phase: Type of Co- solvent Used 93\u003c\/p\u003e \u003cp\u003e3.3.2.2 Mobile Phase: Percentage of Co- solvent Used 94\u003c\/p\u003e \u003cp\u003e3.3.2.3 Mobile Phase: Use of Additives 94\u003c\/p\u003e \u003cp\u003e3.4 Operating Parameters 94\u003c\/p\u003e \u003cp\u003e3.4.1 Effect of the Flow Rate 95\u003c\/p\u003e \u003cp\u003e3.4.2 Effect of the Outlet Pressure (Back- pressure) 95\u003c\/p\u003e \u003cp\u003e3.4.2.1 Effect of Pressure When the Mobile Phase is a Gas- Like Fluid 96\u003c\/p\u003e \u003cp\u003e3.4.2.2 Effect of Pressure When the Mobile Phase is a Liquid- Like Fluid 97\u003c\/p\u003e \u003cp\u003e3.4.3 Effect of Temperature 97\u003c\/p\u003e \u003cp\u003e3.4.3.1 Effect of Temperature When the Mobile Phase is a Gas- Like Fluid 98\u003c\/p\u003e \u003cp\u003e3.4.3.2 Effect of Temperature When the Mobile Phase is a Liquid- Like Fluid 98\u003c\/p\u003e \u003cp\u003e3.5 Detection 99\u003c\/p\u003e \u003cp\u003e3.6 Scale- Up to Preparative Separation 99\u003c\/p\u003e \u003cp\u003e3.7 Conclusion 100\u003c\/p\u003e \u003cp\u003eReferences 101\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Chiral Separation by Capillary Electrophoresis and Capillary Electrophoresis–Mass Spectrometry: Fundamentals, Recent Developments, and Applications 103\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eCharles Clark, Govert W. Somsen, and Isabelle Kohler\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e4.1 Introduction 103\u003c\/p\u003e \u003cp\u003e4.2 Principles of Chiral CE 105\u003c\/p\u003e \u003cp\u003e4.2.1 Electrophoretic Mobility 105\u003c\/p\u003e \u003cp\u003e4.2.2 CE Separation Efficiency 106\u003c\/p\u003e \u003cp\u003e4.2.3 Chiral Resolution in CE 107\u003c\/p\u003e \u003cp\u003e4.2.4 Chiral Micellar Electrokinetic Chromatography and Capillary Electrochromatography 109\u003c\/p\u003e \u003cp\u003e4.3 Short History of Chiral CE Modes 111\u003c\/p\u003e \u003cp\u003e4.3.1 Chiral CE 111\u003c\/p\u003e \u003cp\u003e4.3.2 Chiral MEKC and Chiral CEC 111\u003c\/p\u003e \u003cp\u003e4.4 State of the Art and Recent Developments 112\u003c\/p\u003e \u003cp\u003e4.4.1 Common Chiral Selectors 112\u003c\/p\u003e \u003cp\u003e4.4.2 Ionic Liquids as Chiral Selectors 117\u003c\/p\u003e \u003cp\u003e4.4.3 Nanoparticles as Chiral Selector Carriers 117\u003c\/p\u003e \u003cp\u003e4.4.4 Microfluidic Chiral CE 118\u003c\/p\u003e \u003cp\u003e4.5 Applications of Chiral CE 119\u003c\/p\u003e \u003cp\u003e4.5.1 Pharmaceutical Analysis 119\u003c\/p\u003e \u003cp\u003e4.5.2 Food Analysis 120\u003c\/p\u003e \u003cp\u003e4.5.3 Environmental Analysis 121\u003c\/p\u003e \u003cp\u003e4.5.4 Bioanalysis 123\u003c\/p\u003e \u003cp\u003e4.5.5 Forensic Analysis 126\u003c\/p\u003e \u003cp\u003e4.6 Chiral CE- MS: Strategies and Challenges 126\u003c\/p\u003e \u003cp\u003e4.6.1 Hyphenation Approaches 129\u003c\/p\u003e \u003cp\u003e4.6.1.1 Sheath–Liquid and Sheathless CE- MS Interfacing 129\u003c\/p\u003e \u003cp\u003e4.6.1.2 Partial- Filling Techniques 130\u003c\/p\u003e \u003cp\u003e4.6.1.3 Counter- Migration Techniques 131\u003c\/p\u003e \u003cp\u003e4.6.2 Chiral MEKC- MS 132\u003c\/p\u003e \u003cp\u003e4.6.3 Chiral CEC- MS 133\u003c\/p\u003e \u003cp\u003e4.7 Conclusions and Perspectives 135\u003c\/p\u003e \u003cp\u003eReferences 135\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Chiral Separations at Semi and Preparative Scale 143\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eLarry Miller\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction 143\u003c\/p\u003e \u003cp\u003e5.2 Selection of Operating Conditions 145\u003c\/p\u003e \u003cp\u003e5.3 Batch HPLC Purification 146\u003c\/p\u003e \u003cp\u003e5.3.1 Analytical Method Development for Preparative Separations 146\u003c\/p\u003e \u003cp\u003e5.3.2 Batch HPLC Examples 148\u003c\/p\u003e \u003cp\u003e5.3.2.1 Batch HPLC Example 1 148\u003c\/p\u003e \u003cp\u003e5.3.2.2 Batch HPLC Example 2 149\u003c\/p\u003e \u003cp\u003e5.4 Steady- State Recycle Introduction 151\u003c\/p\u003e \u003cp\u003e5.4.1 SSR Example 1 153\u003c\/p\u003e \u003cp\u003e5.5 Simulated Moving Bed Chromatography – Introduction 154\u003c\/p\u003e \u003cp\u003e5.5.1 SMB Examples for R\u0026amp;D and Separation of Compound 2 156\u003c\/p\u003e \u003cp\u003e5.5.2 Development of a Manufacturing SMB Process (Compound 1) 158\u003c\/p\u003e \u003cp\u003e5.5.3 Cost for SMB Processes 160\u003c\/p\u003e \u003cp\u003e5.6 Introduction to Supercritical Fluid Chromatography 161\u003c\/p\u003e \u003cp\u003e5.6.1 Analytical Method Development for Scale- up to Preparative SFC 162\u003c\/p\u003e \u003cp\u003e5.6.2 Preparative SFC Example 1 163\u003c\/p\u003e \u003cp\u003e5.6.3 Preparative SFC Example 2 163\u003c\/p\u003e \u003cp\u003e5.7 Options for Increasing Purification Productivity 165\u003c\/p\u003e \u003cp\u003e5.7.1 Closed- Loop Recycling 165\u003c\/p\u003e \u003cp\u003e5.7.2 Stacked Injections 166\u003c\/p\u003e \u003cp\u003e5.7.3 Choosing the Best Synthetic Intermediate for Separation 167\u003c\/p\u003e \u003cp\u003e5.7.3.1 Choosing Synthetic Step for Separation – HPLC\/SMB Example 168\u003c\/p\u003e \u003cp\u003e5.7.3.2 Choosing Synthetic Step for Separation – SFC Example 169\u003c\/p\u003e \u003cp\u003e5.7.4 Use of Non- Commercialized CSP 170\u003c\/p\u003e \u003cp\u003e5.7.5 Immobilized CSP for Preparative Resolution 173\u003c\/p\u003e \u003cp\u003e5.7.5.1 Processing of Low Solubility Racemate 173\u003c\/p\u003e \u003cp\u003e5.7.5.2 Preparative Resolution of EMD 53986 174\u003c\/p\u003e \u003cp\u003e5.8 Choosing a Technique for Preparative Enantioseparation 176\u003c\/p\u003e \u003cp\u003e5.9 Conclusion 178\u003c\/p\u003e \u003cp\u003eReferences 179\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart II Chiral Selectors 187\u003cbr\u003e\u003cbr\u003e 6 Polysaccharides 189\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eWeston Umstead, Takafumi Onishi, and Pilar Franco\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e6.1 Introduction 189\u003c\/p\u003e \u003cp\u003e6.2 The Early Years 190\u003c\/p\u003e \u003cp\u003e6.3 Polysaccharide Chiral Separation Mechanism 193\u003c\/p\u003e \u003cp\u003e6.4 Coated Chiral Stationary Phases 197\u003c\/p\u003e \u003cp\u003e6.5 Immobilized Chiral Stationary Phases 201\u003c\/p\u003e \u003cp\u003e6.6 Applications of Polysaccharide- Derived CSPs 208\u003c\/p\u003e \u003cp\u003e6.6.1 Analytical Applications 210\u003c\/p\u003e \u003cp\u003e6.6.1.1 Pharmaceuticals 211\u003c\/p\u003e \u003cp\u003e6.6.1.2 Agrochemicals 218\u003c\/p\u003e \u003cp\u003e6.6.1.3 Food Analysis 219\u003c\/p\u003e \u003cp\u003e6.6.2 Preparative Applications 220\u003c\/p\u003e \u003cp\u003e6.7 Summation 224\u003c\/p\u003e \u003cp\u003eReferences 224\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Macrocyclic Antibiotics and Cyclofructans 247\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eSaba Aslani, Alain Berthod, and Daniel W. Armstrong\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e7.1 Introduction 247\u003c\/p\u003e \u003cp\u003e7.2 Macrocyclic Glycopeptides Physicochemical Properties 248\u003c\/p\u003e \u003cp\u003e7.3 Using the Chiral Macrocyclic Glycopeptides Stationary Phases 253\u003c\/p\u003e \u003cp\u003e7.3.1 Mobile Phases and Chromatographic Modes 253\u003c\/p\u003e \u003cp\u003e7.3.2 Chromatographic Enantioseparations 254\u003c\/p\u003e \u003cp\u003e7.3.2.1 Amino Acids and Peptides 254\u003c\/p\u003e \u003cp\u003e7.3.2.2 Chiral Compounds 257\u003c\/p\u003e \u003cp\u003e7.3.2.3 Particle Structure 257\u003c\/p\u003e \u003cp\u003e7.4 Using and Protecting Macrocyclic Glycopeptide Chiral Columns 260\u003c\/p\u003e \u003cp\u003e7.4.1 Operating Conditions 260\u003c\/p\u003e \u003cp\u003e7.4.2 Storage 261\u003c\/p\u003e \u003cp\u003e7.5 Cyclofructans 261\u003c\/p\u003e \u003cp\u003e7.5.1 Cyclofructan Structure and Properties 261\u003c\/p\u003e \u003cp\u003e7.5.2 Chiral Separations with Cyclofructan- Based Stationary Phases 264\u003c\/p\u003e \u003cp\u003e7.5.3 Cyclofructan Stationary Phases Used in the HILIC Mode 264\u003c\/p\u003e \u003cp\u003e7.5.4 Cyclofructan Stationary Phases Used in Supercritical Fluid Chromatography 266\u003c\/p\u003e \u003cp\u003e7.6 Conclusions 267\u003c\/p\u003e \u003cp\u003eReferences 268\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Cyclodextrins 273\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eGerhard K. E. Scriba, Mari- Luiza Konjaria, and Sulaiman Krait\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e8.1 Introduction 273\u003c\/p\u003e \u003cp\u003e8.2 Structure and Properties 274\u003c\/p\u003e \u003cp\u003e8.3 Cyclodextrin Complexes 279\u003c\/p\u003e \u003cp\u003e8.4 Application in Separation Science 288\u003c\/p\u003e \u003cp\u003e8.4.1 Gas Chromatography 288\u003c\/p\u003e \u003cp\u003e8.4.1.1 Types of Cyclodextrins 289\u003c\/p\u003e \u003cp\u003e8.4.1.2 Types of Columns 289\u003c\/p\u003e \u003cp\u003e8.4.1.3 Separation Mechanisms 291\u003c\/p\u003e \u003cp\u003e8.4.1.4 Applications 293\u003c\/p\u003e \u003cp\u003e8.4.2 Thin- Layer Chromatography 294\u003c\/p\u003e \u003cp\u003e8.4.3 High- Performance Liquid Chromatography 294\u003c\/p\u003e \u003cp\u003e8.4.3.1 Types of Columns 295\u003c\/p\u003e \u003cp\u003e8.4.3.2 Types of Cyclodextrins 297\u003c\/p\u003e \u003cp\u003e8.4.3.3 Separation Mechanisms 298\u003c\/p\u003e \u003cp\u003e8.4.3.4 Applications 300\u003c\/p\u003e \u003cp\u003e8.4.4 Supercritical Fluid Chromatography 300\u003c\/p\u003e \u003cp\u003e8.4.5 Capillary Electromigration Techniques 301\u003c\/p\u003e \u003cp\u003e8.4.5.1 Types of Cyclodextrins 301\u003c\/p\u003e \u003cp\u003e8.4.5.2 Separation Mechanisms 302\u003c\/p\u003e \u003cp\u003e8.4.5.3 Migration Modes and Enantiomer Migration Order Using CDs as Selectors 304\u003c\/p\u003e \u003cp\u003e8.4.5.4 Applications 310\u003c\/p\u003e \u003cp\u003e8.4.6 Membrane Technologies 312\u003c\/p\u003e \u003cp\u003e8.5 Miscellaneous Applications 314\u003c\/p\u003e \u003cp\u003e8.6 Conclusions and Outlook 315\u003c\/p\u003e \u003cp\u003eReferences 315\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 Pirkle Type 325\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eMaria Elizabeth Tiritan, Madalena Pinto, and Carla Fernandes\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e9.1 Introduction 325\u003c\/p\u003e \u003cp\u003e9.2 CSPs Developed by Pirkle’s Group: Chronological Evolution 327\u003c\/p\u003e \u003cp\u003e9.3 Pirkle- Type CSPs Developed by Other Research Groups 334\u003c\/p\u003e \u003cp\u003e9.4 Example of Applications in Analytical and Preparative Scales 340\u003c\/p\u003e \u003cp\u003e9.4.1 Analytical Applications 341\u003c\/p\u003e \u003cp\u003e9.4.2 Preparative Applications 349\u003c\/p\u003e \u003cp\u003e9.5 Conclusions and Perspectives 349\u003c\/p\u003e \u003cp\u003eReferences 350\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 Proteins 363\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eJun Haginaka\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e10.1 Introduction 363\u003c\/p\u003e \u003cp\u003e10.2 Preparation of Protein- and Glycoprotein- Based Chiral Stationary Phases 364\u003c\/p\u003e \u003cp\u003e10.3 Types of Protein- and Glycoprotein- Based Chiral Stationary Phases 368\u003c\/p\u003e \u003cp\u003e10.3.1 Proteins 368\u003c\/p\u003e \u003cp\u003e10.3.1.1 Bovine Serum Albumin 368\u003c\/p\u003e \u003cp\u003e10.3.1.2 Human Serum Albumin 370\u003c\/p\u003e \u003cp\u003e10.3.1.3 Trypsin and α- Chymotrypsin 372\u003c\/p\u003e \u003cp\u003e10.3.1.4 Lysozyme and Pepsin 372\u003c\/p\u003e \u003cp\u003e10.3.1.5 Fatty Acid- Binding Protein 373\u003c\/p\u003e \u003cp\u003e10.3.1.6 Penicillin G Acylase 375\u003c\/p\u003e \u003cp\u003e10.3.1.7 Streptavidin 375\u003c\/p\u003e \u003cp\u003e10.3.1.8 Lipase 376\u003c\/p\u003e \u003cp\u003e10.3.2 Glycoproteins 376\u003c\/p\u003e \u003cp\u003e10.3.2.1 Human α \u003csub\u003e1\u003c\/sub\u003e - Acid Glycoprotein 376\u003c\/p\u003e \u003cp\u003e10.3.2.2 Chicken Ovomucoid 377\u003c\/p\u003e \u003cp\u003e10.3.2.3 Chicken α \u003csub\u003e1\u003c\/sub\u003e- Acid Glycoprotein 378\u003c\/p\u003e \u003cp\u003e10.3.2.4 Avidin 380\u003c\/p\u003e \u003cp\u003e10.3.2.5 Riboflavin- Binding Protein and Ovotransferrin 380\u003c\/p\u003e \u003cp\u003e10.3.2.6 Cellobiohydrolase 381\u003c\/p\u003e \u003cp\u003e10.3.2.7 Glucoamylase 383\u003c\/p\u003e \u003cp\u003e10.3.2.8 Antibody (Immunoglobulin G) 385\u003c\/p\u003e \u003cp\u003e10.3.2.9 Nicotinic Acetylcholine Receptor and Human Liver Organic Cation Transporter 387\u003c\/p\u003e \u003cp\u003e10.4 Chiral Recognition Mechanisms on Proteinand Glycoprotein- Based Chiral Stationary Phases 387\u003c\/p\u003e \u003cp\u003e10.4.1 Human Serum Albumin 387\u003c\/p\u003e \u003cp\u003e10.4.2 Penicillin G Acylase 389\u003c\/p\u003e \u003cp\u003e10.4.3 Human α \u003csub\u003e1\u003c\/sub\u003e- Acid Glycoprotein 390\u003c\/p\u003e \u003cp\u003e10.4.4 Turkey Ovomucoid 392\u003c\/p\u003e \u003cp\u003e10.4.5 Chicken α \u003csub\u003e1\u003c\/sub\u003e- Acid Glycoprotein 393\u003c\/p\u003e \u003cp\u003e10.4.6 Cellobiohydrolase 395\u003c\/p\u003e \u003cp\u003e10.4.7 Antibody 396\u003c\/p\u003e \u003cp\u003e10.4.8 Nicotinic Acetylcholine Receptor and Human Liver Organic Cation Transporter 400\u003c\/p\u003e \u003cp\u003e10.5 Conclusions 401\u003c\/p\u003e \u003cp\u003eReferences 402\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 Chiral Stationary Phases Derived from Cinchona Alkaloids 415\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eMichael Lämmerhofer and Wolfgang Lindner\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e11.1 Introduction 415\u003c\/p\u003e \u003cp\u003e11.2 Cinchona Alkaloid- Derived Chiral Stationary Phases 416\u003c\/p\u003e \u003cp\u003e11.3 Chiral Recognition 420\u003c\/p\u003e \u003cp\u003e11.4 Chromatographic Retention Mechanisms 424\u003c\/p\u003e \u003cp\u003e11.4.1 Multimodal Applicability 424\u003c\/p\u003e \u003cp\u003e11.4.2 Surface Charge of Cinchonan- Based CSPs 424\u003c\/p\u003e \u003cp\u003e11.4.3 Retention Mechanisms and Models, and Method Development on Chiral WAX CSPs 427\u003c\/p\u003e \u003cp\u003e11.4.4 Retention Mechanisms and Method Development on ZWIX CSPs 430\u003c\/p\u003e \u003cp\u003e11.5 Structural Variants of Cinchona Alkaloid CSPs and Immobilization Chemistries 436\u003c\/p\u003e \u003cp\u003e11.6 Cinchonan- Based UHPLC Column Technologies 442\u003c\/p\u003e \u003cp\u003e11.7 Applications 446\u003c\/p\u003e \u003cp\u003e11.7.1 Pharmaceutical and Biotechnological Applications 446\u003c\/p\u003e \u003cp\u003e11.7.2 Biomedical Applications 453\u003c\/p\u003e \u003cp\u003e11.8 Conclusions 460\u003c\/p\u003e \u003cp\u003eReferences 460\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart III Methods for Stereochemical Elucidation 473\u003cbr\u003e\u003cbr\u003e 12 X- Ray Crystallography for Stereochemical Elucidation 475\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eAdemir F. Morel and Robert A. Burrow\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e12.1 Introduction 475\u003c\/p\u003e \u003cp\u003e12.2 Absolute Structure and Absolute Configuration 476\u003c\/p\u003e \u003cp\u003e12.3 Best Practices 482\u003c\/p\u003e \u003cp\u003e12.4 Structure Validation 486\u003c\/p\u003e \u003cp\u003e12.5 The Absolute Configuration of (+)- Lanatine A 486\u003c\/p\u003e \u003cp\u003e12.6 The Absolute Configuration of the Diacetylated Form of Acrenol and the Acetylated Form of Humirianthol 488\u003c\/p\u003e \u003cp\u003e12.7 The Absolute Configuration of Ester Form of Clemateol 491\u003c\/p\u003e \u003cp\u003e12.8 Relative Configurations of Waltherione A, Waltherione B, and Vanessine 492\u003c\/p\u003e \u003cp\u003e12.9 The Absolute Configuration of Condaline A 493\u003c\/p\u003e \u003cp\u003e12.10 CSD Deposit Numbers 496\u003c\/p\u003e \u003cp\u003e12.11 Conclusions and Future Directions 498\u003c\/p\u003e \u003cp\u003eReferences 498\u003c\/p\u003e \u003cp\u003e\u003cb\u003e13 NMR for Stereochemical Elucidation 505\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eXiaolu Li, Xiaoliang Yang, and Han Sun\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e13.1 Conventional NMR Methods for Stereochemical Elucidation 505\u003c\/p\u003e \u003cp\u003e13.1.1 Determination of the Planar Structure Using 1D \u003csup\u003e1\u003c\/sup\u003e H, \u003csup\u003e13\u003c\/sup\u003e C NMR (DEPT), 2D HSQC, COSY, TOCSY, HMBC 506\u003c\/p\u003e \u003cp\u003e13.1.2 Determination of Relative Configuration Using J- Couplings and NOEs\/ROEs 507\u003c\/p\u003e \u003cp\u003e13.1.2.1 Scalar Coupling 507\u003c\/p\u003e \u003cp\u003e13.1.2.2 NOE\/ROE 510\u003c\/p\u003e \u003cp\u003e13.1.2.3 Examples of Stereochemical Elucidation Using J- Couplings and NOEs\/ROEs 510\u003c\/p\u003e \u003cp\u003e13.2 Determination of the Relative Configuration Using Anisotropic NMR- Based Methods 516\u003c\/p\u003e \u003cp\u003e13.2.1 Basic Principles of Anisotropic NMR Parameters 517\u003c\/p\u003e \u003cp\u003e13.2.2 Alignment Media 518\u003c\/p\u003e \u003cp\u003e13.2.2.1 Preparation of Anisotropic Sample with PMMA Gel 520\u003c\/p\u003e \u003cp\u003e13.2.2.2 Preparation of Anisotropic Sample with AAKLVFF 521\u003c\/p\u003e \u003cp\u003e13.2.3 Acquisition of the Anisotropic NMR Data 522\u003c\/p\u003e \u003cp\u003e13.2.4 Computational Approaches for Analyzing Anisotropic NMR Data 525\u003c\/p\u003e \u003cp\u003e13.2.5 Successful Examples of Determination of Relative Configuration of Challenging Molecules Using Anisotropic NMR 528\u003c\/p\u003e \u003cp\u003e13.3 Determination of the Relative Configuration Using DP 4 Probability and CASE- 3D 529\u003c\/p\u003e \u003cp\u003e13.4 Determination of the Absolute Configuration Using a Combination of NMR Spectroscopy and Chiroptical Spectroscopy 533\u003c\/p\u003e \u003cp\u003e13.5 Determination of the Absolute Configuration Using NMR Alone 534\u003c\/p\u003e \u003cp\u003e13.5.1 Mosher Ester Analysis 535\u003c\/p\u003e \u003cp\u003e13.5.2 Other Chiral Derivatizing Agents 536\u003c\/p\u003e \u003cp\u003e13.6 Future Perspective 536\u003c\/p\u003e \u003cp\u003eReferences 537\u003c\/p\u003e \u003cp\u003e\u003cb\u003e14 Absolute Configuration from Chiroptical Spectroscopy 551\u003cbr\u003e \u003c\/b\u003e\u003ci\u003eFernando Martins dos Santos Junior and João Marcos Batista Junior\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e14.1 Introduction 551\u003c\/p\u003e \u003cp\u003e14.2 Chiroptical Methods 554\u003c\/p\u003e \u003cp\u003e14.2.1 Optical Rotation and Optical Rotatory Dispersion 554\u003c\/p\u003e \u003cp\u003e14.2.1.1 Instrumentation 556\u003c\/p\u003e \u003cp\u003e14.2.1.2 Measurements 557\u003c\/p\u003e \u003cp\u003e14.2.2 Electronic Circular Dichroism 558\u003c\/p\u003e \u003cp\u003e14.2.2.1 Instrumentation 560\u003c\/p\u003e \u003cp\u003e14.2.2.2 Measurements 561\u003c\/p\u003e \u003cp\u003e14.2.3 Vibrational Circular Dichroism and Raman Optical Activity 561\u003c\/p\u003e \u003cp\u003e14.2.3.1 Instrumentation 563\u003c\/p\u003e \u003cp\u003e14.2.3.2 Measurements 565\u003c\/p\u003e \u003cp\u003e14.2.4 Simulation of Chiroptical Properties 567\u003c\/p\u003e \u003cp\u003e14.2.4.1 Common Theoretical Steps 568\u003c\/p\u003e \u003cp\u003e14.2.4.2 OR and ORD Simulations 570\u003c\/p\u003e \u003cp\u003e14.2.4.3 ECD Simulations 572\u003c\/p\u003e \u003cp\u003e14.2.4.4 VCD and ROA Simulations 573\u003c\/p\u003e \u003cp\u003e14.2.5 Examples of Application 575\u003c\/p\u003e \u003cp\u003e14.2.5.1 OR 575\u003c\/p\u003e \u003cp\u003e14.2.5.2 ORD 577\u003c\/p\u003e \u003cp\u003e14.2.5.3 ECD 578\u003c\/p\u003e \u003cp\u003e14.2.5.4 VCD 579\u003c\/p\u003e \u003cp\u003e14.2.5.5 ROA 581\u003c\/p\u003e \u003cp\u003e14.2.5.6 Association of Different Chiroptical Methods 582\u003c\/p\u003e \u003cp\u003e14.3 Concluding Remarks 585\u003c\/p\u003e \u003cp\u003eReferences 586\u003c\/p\u003e \u003cp\u003eIndex 593\u003c\/p\u003e","brand":"John Wiley \u0026 Sons Inc","offers":[{"title":"Default Title","offer_id":51039269126487,"sku":"9781119802259","price":170.1,"currency_code":"GBP","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0817\/1739\/5799\/files\/9781119802259.jpg?v=1750943114","url":"https:\/\/bookcurl.com\/products\/chiral-separations-and-stereochemical-elucidation-9781119802259","provider":"Book Curl","version":"1.0","type":"link"}