Chiral Separation Techniques: A Practical Approach

Chirality describes the fact that a particular molecule can have a "right–hand" structure or its mirrored "left–hand" structure, both of which may display very different characteristics. For example, a "right–hand" structure can be an important active substance for a drug while its "left–hand" variation is highly toxic. For this reason, chiral separation techniques are indispensable for production and safety testing in biotechnology, food and pharmaceutical industries.
Thoroughly revised, with either entirely new or completely updated contents, this is a practical manual for the small and large–scale preparation of enantiomerically pure products. The result is a vital resource for meeting the highest purity standards in the manufacture of chiral pharmaceuticals, food additives and related compounds. All the approaches covered here are highly relevant to modern manufacturing and quality control schemes in the pharmaceutical and biotech industries, addressing the increasingly important issue of drug safety in view of tougher regulatory standards worldwide.

Spis treści:
Preface.
List of Contributors.
1 Method Development and Optimization of Enantioseparations Using Macrocyclic Glycopeptide Chiral Stationary Phases (Thomas E. Beesley and J.T. Lee).
1.1 Introduction.
1.2 Structural Characteristics of Macrocyclic Glycopeptide CSPs.
1.3 Enantioselectivity as a Function of Molecular Recognition.
1.4 Complementary Effects.
1.5 Method Development.
1.6 Optimization Procedures.
1.7 Amino Acid and Peptide Analysis.
1.8 Conclusion.
Acknowledgments.
References.
2 Role of Polysaccharides in Chiral Separations by Liquid Chromatography and Capillary Electrophoresis (Imran Ali and Hassan Y. Aboul–Enein).
2.1 Introduction.
2.2 Structures of Polysaccharide Chiral Selectors.
2.3 Properties of Polysaccharide CSPs.
2.4 Applications.
2 .5 Optimization of Chiral Separations.
2.6 Chiral Recognition Mechanisms.
2.7 Chiral Separation by Sub– and Supercritical Fluid Chromatography.
2.8 Chiral Separation by Capillary Electrochromatography.
2.9 Chiral Separation by Thin–layer Chromatography.
2.10 Chiral Separation by Capillary Electrophoresis.
2.11 Conclusion.
References.
3 Analytical and Preparative Potential of Immobilized Polysaccharide–derived Chiral Stationary Phases (Tong Zhang and Pilar Franco).
3.1 Introduction.
3.2 Scope of Immobilized Polysaccharide–derived CSPs.
3.3 Beneficial Characteristics of Immobilized Polysaccharide–derived CSPs.
3.4 Method Development on Immobilized Polysaccharide–derived CSPs.
3.5 Regeneration of Immobilized CSPs – Why, How and When.
3.6 Conclusions and Perspectives.
References.
4 Chiral Separations Using Supercritical Fluid Chromatography (Karen W. Phinney and Rodger W. Stringham).
4.1 Introduction.
4.2 Overview of SFC.
4.3 Chiral Stationary Phases in SFC.
4.4 Mobile Phase Effects in SFC.
4.5 Preparative–scale Separations.
References.
5 Chiral Separation by Ligand Exchange (Gerald Gübitz and Martin G. Schmid).
5.1 Introduction.
5.2 Chiral Ligand–exchange Chromatography.
5.3 Complexation Gas Chromatography.
5.4 LE–Electromigration Techniques.
List of Abbreviations.
References.
6 Advances in Simulated Moving Bed Chromatographic Separations (Pedro Sá Gomes, Mirjana Minceva, Luís S. Pais, and Alírio E. Rodrigues).
6.1 Introduction.
6.2 Modeling Strategies.
6.3 Simulation.
6.4 Novel SMB Configurations.
6.5 Improvements in Operation Conditions Evaluation (Separation Volume Method).
6.6 Conclusions.
References.
7 Less Common Applications of Enantioselective HPLC Using the SMB Technology in the Pharmaceutical Industry ( Stefanie Abel and Markus Juza).
7.1 Introduction – From an Emerging Technology to a Classical Unit Operation.
7.2 Unbalanced Separations and Multi–component Separations Using SMB.
7.3 Unusual Isotherms and Adsorption Behavior.
7.4 Applications of Various Column Configurations.
7.5 Application of Solvent Gradients.
7.6 Chemistry and Racemization.
7.7 Future Developments.
7.8 Conclusion.
Notation.
Greek Letters.
Subscripts.
Acknowledgments.
References.
8 Enantiomer Separation by Chiral Crown Ether Stationary Phases (Myung Ho Hyun).
8.1 Introduction.
8.2 Development of CSPs.
8.3 Applications of CSPs.
8.4 Composition of Mobile Phase.
8.5 Temperature Effect.
8.6 Conclusion.
Acknowledgment.
References.
9 Enantioselective Separation of Amino Acids and Hydroxy Acids by Ligand Exchange with Copper(II) Complexes in HPLC (Chiral Eluent) and in Fast Sensing Systems (Rosangela Marchelli, Roberto Corradini, Gianni Galaverna, Arnaldo Dossena, Francesco Dallavalle, and Stefano Sforza).
9.1 Introduction.
9.2 Enantiomeric Separation of Amino Acids and Hydroxy Acids with the Chiral Selectors Added to the Mobile Phase in HPLC (CMPs).
9.3 Dynamically Coated Stationary Phases.
9.4 Comparison Between Enantiomeric Separations Obtained with the Chiral Selector Bound to the Stationary Phase or Added to the Eluent.
9.5 Mixed Inclusion–Ligand–exchange Chromatography.
9.6 Ligand Exchange in Fast Sensing Systems.
Acknowledgment.
References.
10 Enantiomer Separation by Capillary Electrophoresis (Gerhard K. E. Scriba).
10.1 Introduction.
10.2 Modes of Capillary Electromigration Techniques.
10.3 Theory of Electrophoretic Separations.
10.4 Enantiomer Separations.
10.5 Applications.
10.6 Method Development and Validation.
10.7 Migration Models.
10.8 Enantiomer Migration Order.
10.9 Future Trends.
References .
11 Counter–current Chromatography in the Separation of Enantiomers (Eva Pérez and Cristina Minguillón).
11.1 Introduction.
11.2 Instrumentation.
11.3 Some Thoughts on CCC Enantioseparation.
11.4 Chiral Selectors Used in CCC Enantioseparations.
11.5 pH–zone–refining CCC.
11.6 Sample Resolution in CCC.
11.7 Continuous CPC.
11.8 Conclusions and Future Trends.
Acknowledgments.
References.
12 Separation of Enantiomers Using Molecularly Imprinted Polymers (Börje Sellergren).
12.1 Introduction.
12.2 Fundamental Studies Using Enantiomers as Model Templates.
12.3 Using Frontal Analysis to Elucidate Retention Mechanisms.
12.4 Approaches to Binding Site Design.
12.5 Other Formats: Beads, Monoliths, and Films.
12.6 Other Matrices for Imprinting of Enantiomers.
12.7 Conclusions.
References.
13 Enantioselective Biosensors (Raluca–Ioana Stefan–van Staden, Jacobus Frederick van Staden, and Hassan Y. Aboul–Enein).
13.1 Introduction.
13.2 The Design of Enantioselective Electrochemical Biosensors.
13.3 Applications of Enantioselective Analysis.
13.4 Conclusion.
References.
14 Chiral Analysis in Capillary Electrochromatography (CEC) and CEC Coupled to Mass Spectrometry (Jie Zheng and Shahab A. Shamsi).
14.1 Introduction.
14.2 CEC Column Technologies for Chiral Separation.
14.3 Chiral Stationary Phases for CEC.
14.4 Chiral CEC Coupled to Mass Spectrometric Detection.
14.5 Conclusions.
List of Abbreviations.
References.
15 Chiral Analysis Using Polymeric Surfactants in Micellar Electrokinetic Chromatography (MEKC) and MEKC Coupled to Mass Spectrometry (Syed A. A. Rizvi and Shahab A. Shamsi).
15.1 Introduction.
15.2 Chiral Anionic Surfactants.
15.3 Chiral Cationic Surfactants.
15.4 Coupling of MEKC to Mass Spectrometry Using Polymeric Surfactants.
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