Chiral separations and stereochemical elucidation : fundamentals, methods, and applications /: fundamentals, methods, and applications. (2023)

• Record Type: Book
• Further Information: Note: Edited by Quezia Bezerra Cass, Maria Elizabeth Tiritan, João Marcos Batista Junior, Juliana Cristina Barreiro.
• Editors: Cass, Quezia Bezerra; Tiritan, Maria Elizabeth; Jr, Batista, João Marcos; Barreiro, Juliana Cristina
• Contents: List of Contributors xv Preface xix Part I Fundamentals of Chiral Separation 1 1 Chiral Separation by LC 3; Juliana Cristina Barreiro and Quezia Bezerra Cass 1.1 Introduction 3 1.2 Workflow for LC Chiral Method Development 7 1.3 New Column Technologies 9 1.4 Selected Examples of Fast Separation 12 1.5 Chiral 2D-LC 14 1.5.1 LC–LC and mLC–LC 14 1.5.2 LC × LC and sLC × LC 17 1.6 Future and Perspectives 19 References 20 2 Chiral Separation by GC 27; Oliver Trapp 2.1 Introduction 27 2.2 Chiral Recognition in Gas Chromatography 29 2.2.1 Chiral Recognition by Hydrogen Bonding 31 2.2.2 Chiral Recognition Using Chiral Metal Complexes 31 2.2.3 Chiral Recognition by Host–Guest Interactions 31 2.3 Preparation of Fused-Silica Capillaries for GC with CSPs 33 2.4 Application of CSPs in Chiral Gas Chromatography 34 2.4.1 CSPs with Diamide Selectors 34 2.4.1.1 Chirasil-Val 34 2.4.2 CSPs with CD Selectors 35 2.4.2.1 Heptakis(2, 3, 6-tri-O -Methyl)-β-Cyclodextrin(Permethyl-β-Cyclodextrin) 38 2.4.2.2 Heptakis(2, 3, 6-tri-O -Methyl)-β-Cyclodextrin Immobilized to Hydrido Dimethyl Polysiloxane (Chirasil-β-Dex) 39 2.4.2.3 Heptakis(2, 6-di-O -Methyl-3-O -Pentyl)-β-Cyclodextrin 43 2.4.2.4 Hexakis-(2, 3, 6-tri-O -Pentyl)-α-Cyclodextrin 47 2.4.2.5 Heptakis(2, 3, 6-tri-O -Pentyl)-β-Cyclodextrin 48 2.4.2.6 Hexakis-(3-O -Acetyl-2, 6-di-O -Pentyl)-α-Cyclodextrin 51 2.4.2.7 Heptakis(3-O -Acetyl-2, 6-di-O-Pentyl)-β-Cyclodextrin 51 2.4.2.8 Octakis(3-O -Butyryl-2, 6-di-O-Pentyl)-γ-Cyclodextrin 53 2.4.2.9 Hexakis/Heptakis/Octakis(2, 6-di-O-Alkyl-3-O-Trifluoroacetyl)-α/β/γ-Cyclodextrins 57 2.4.2.10 Heptakis(2, 3-di-O -Acetyl-6-O - tert -Butyldimethylsilyl)-β-Cyclodextrin (DIAC-6-TBDMS-β-CD) 58 2.4.2.11 Heptakis(2, 3-di-O -Methyl-6-O - tert -Butyldimethylsilyl)-β-Cyclodextrin (DIME-6-TBDMS-β-CD) 58 2.4.3 Cyclofructans 62 2.4.4 CSPs with Metal Complexes 65 2.5 Conclusion 69 References 69 3 Chiral Separation by Supercritical Fluid Chromatography 85; Emmanuelle Lipka 3.1 Introduction 85 3.2 Characteristics and Properties of Supercritical Fluids 87 3.3 Development of a Chiral SFC Method 89 3.3.1 Chiral Stationary Phases 89 3.3.2 Mobile Phases 91 3.3.2.1 Mobile Phase: Type of Co-solvent Used 93 3.3.2.2 Mobile Phase: Percentage of Co-solvent Used 94 3.3.2.3 Mobile Phase: Use of Additives 94 3.4 Operating Parameters 94 3.4.1 Effect of the Flow Rate 95 3.4.2 Effect of the Outlet Pressure (Back-pressure) 95 3.4.2.1 Effect of Pressure When the Mobile Phase is a Gas-Like Fluid 96 3.4.2.2 Effect of Pressure When the Mobile Phase is a Liquid-Like Fluid 97 3.4.3 Effect of Temperature 97 3.4.3.1 Effect of Temperature When the Mobile Phase is a Gas-LikeFluid 98 3.4.3.2 Effect of Temperature When the Mobile Phase is a Liquid-Like Fluid 98 3.5 Detection 99 3.6 Scale-Up to Preparative Separation 99 3.7 Conclusion 100 References 101 4 Chiral Separation by Capillary Electrophoresis and Capillary Electrophoresis–Mass Spectrometry: Fundamentals, Recent Developments, and Applications 103; Charles Clark, Govert W. Somsen, and Isabelle Kohler 4.1 Introduction 103 4.2 Principles of Chiral CE 105 4.2.1 Electrophoretic Mobility 105 4.2.2 CE Separation Efficiency 106 4.2.3 Chiral Resolution in CE 107 4.2.4 Chiral Micellar Electrokinetic Chromatography and Capillary Electrochromatography 109 4.3 Short History of Chiral CE Modes 111 4.3.1 Chiral CE 111 4.3.2 Chiral MEKC and Chiral CEC 111 4.4 State of the Art and Recent Developments 112 4.4.1 Common Chiral Selectors 112 4.4.2 Ionic Liquids as Chiral Selectors 117 4.4.3 Nanoparticles as Chiral Selector Carriers 117 4.4.4 Microfluidic Chiral CE 118 4.5 Applications of Chiral CE 119 4.5.1 Pharmaceutical Analysis 119 4.5.2 Food Analysis 120 4.5.3 Environmental Analysis 121 4.5.4 Bioanalysis 123 4.5.5 Forensic Analysis 126 4.6 Chiral CE-MS: Strategies and Challenges 126 4.6.1 Hyphenation Approaches 129 4.6.1.1 Sheath–Liquid and Sheathless CE-MS Interfacing 129 4.6.1.2 Partial-Filling Techniques 130 4.6.1.3 Counter-Migration Techniques 131 4.6.2 Chiral MEKC-MS 132 4.6.3 Chiral CEC-MS 133 4.7 Conclusions and Perspectives 135 References 135 5 Chiral Separations at Semi and Preparative Scale 143; Larry Miller 5.1 Introduction 143 5.2 Selection of Operating Conditions 145 5.3 Batch HPLC Purification 146 5.3.1 Analytical Method Development for Preparative Separations 146 5.3.2 Batch HPLC Examples 148 5.3.2.1 Batch HPLC Example 1 148 5.3.2.2 Batch HPLC Example 2 149 5.4 Steady-State Recycle Introduction 151 5.4.1 SSR Example 1 153 5.5 Simulated Moving Bed Chromatography – Introduction 154 5.5.1 SMB Examples for R&D and Separation of Compound 2 156 5.5.2 Development of a Manufacturing SMB Process (Compound 1) 158 5.5.3 Cost for SMB Processes 160 5.6 Introduction to Supercritical Fluid Chromatography 161 5.6.1 Analytical Method Development for Scale-up to Preparative SFC 162 5.6.2 Preparative SFC Example 1 163 5.6.3 Preparative SFC Example 2 163 5.7 Options for Increasing Purification Productivity 165 5.7.1 Closed-Loop Recycling 165 5.7.2 Stacked Injections 166 5.7.3 Choosing the Best Synthetic Intermediate for Separation 167 5.7.3.1 Choosing Synthetic Step for Separation – HPLC/SMB Example 168 5.7.3.2 Choosing Synthetic Step for Separation – SFC Example 169 5.7.4 Use of Non-Commercialized CSP 170 5.7.5 Immobilized CSP for Preparative Resolution 173 5.7.5.1 Processing of Low Solubility Racemate 173 5.7.5.2 Preparative Resolution of EMD 53986 174 5.8 Choosing a Technique for Preparative Enantioseparation 176 5.9 Conclusion 178 References 179 Part II Chiral Selectors 187 6 Polysaccharides 189; Weston Umstead, Takafumi Onishi, and Pilar Franco 6.1 Introduction 189 6.2 The Early Years 190 6.3 Polysaccharide Chiral Separation Mechanism 193 6.4 Coated Chiral Stationary Phases 197 6.5 Immobilized Chiral Stationary Phases 201 6.6 Applications of Polysaccharide-Derived CSPs 208 6.6.1 Analytical Applications 210 6.6.1.1 Pharmaceuticals 211 6.6.1.2 Agrochemicals 218 6.6.1.3 Food Analysis 219 6.6.2 Preparative Applications 220 6.7 Summation 224 References 224 7 Macrocyclic Antibiotics and Cyclofructans 247; Saba Aslani, Alain Berthod, and Daniel W. Armstrong 7.1 Introduction 247 7.2 Macrocyclic Glycopeptides Physicochemical Properties 248 7.3 Using the Chiral Macrocyclic Glycopeptides Stationary Phases 253 7.3.1 Mobile Phases and Chromatographic Modes 253 7.3.2 Chromatographic Enantioseparations 254 7.3.2.1 Amino Acids and Peptides 254 7.3.2.2 Chiral Compounds 257 7.3.2.3 Particle Structure 257 7.4 Using and Protecting Macrocycl
• Edition: 1st
• Publisher Details: Hoboken : John Wiley & Sons, Inc
• Publication Date: 2023
• Extent: 1 online resource (640 pages)
• Subjects: 541.223; Chirality; Stereochemistry
• Languages: English
• ISBNs: 9781119802266
• Related ISBNs: 9781119802259
• Notes: Note: Includes bibliographical references and index.; Note: Description based on CIP data; resource not viewed.
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