Thin Layer Chromatography in Chiral Separations and Analysis
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Summary
Thin layer chromatography (TLC) is well suited for performing enantioseparations for research as well as larger-scale applications. A fast, inexpensive, and versatile separation technique, there are many practical considerations that contribute to its effectiveness. Thin Layer Chromatography in Chiral Separations and Analysis is the first book to focus solely on the theory, capabilities, and applications of TLC for direct and indirect enantioseparations.
The first part of the book examines the fundamental principles of chirality and TLC. It describes the necessary materials, laboratory equipment, procedures, and strategies for the separation, quantification, isolation, and analysis of chiral compounds. The second part evaluates the real-world enantioseparations and densitometric analyses. Emphasizing pharmaceutical applications, the book discusses chiral separation mechanisms and methods for analyzing the chiral purity of diastereoisomers, amino acids, beta-blockers, and NSAIDS. Topics also include commercial stationary phases and chiral modifiers of mobile phases.
Thin Layer Chromatography in Chiral Separations and Analysis presents a unified perspective of theory and experimental details underlying the collective developments in the field. The book offers scientists in a variety of disciplines and levels of expertise a complete guide to understanding the current and potential applications of chiral TLC.
Table of Contents
Preface; T. Kowalska, J. Sherma
Overview of the Field of Chiral TLC and Organization of the Book; T. Kowalska, J. Sherma
Chirality; P. Kuś, A. Sochanik
Chirality in Nature
Methods for determination of compounds’ stereochemistry
On the methods of obtaining stereoisomers
Stereochemistry of organic compounds
Stereochemistry of complexes
Commercial Stationary Phases for Enantioseparations; J. Sherma
Chiral stationary phases and chiral-coated phases
Nonchiral plates used with chiral mobile phases
Quantitative analysis of enantiomers by densitometry
Planar Chromatographic Enantioseparations on Non-Commercial CSPs; L. Lepri, A. Cincinelli, M. Del Bubba
Cellulose
Cellulose triacetate
Cellulose tribenzoate
Cellulose tricarbammate
Molecular imprinting polymers; MIPs
b-Cyclodextrin; b-CD bonded silica gel
Planar Chromatographic Enantioseparations on Non-Commercial CCPs; L. Lepri, A. Cincinelli, M. Del Bubba
Layers impregnated with metal ion complexes as chiral selectors; CLEC
Acidic or basic chiral impregnating agents in planar chromatography
Chiral Modifiers of Mobile Phases; D. Agbaba, B.M. Ivković
b-Cyclodextrins and their derivatives as mobile phase additives
Macrocyclics antibiotics as mobile phase additives
Chiral counter ions in mobile phase
BSA as mobile phase additives
An Overview of the Chiral Separation Mechanisms; A.M. Siouffi, P. Piras
Solute-chiral selector complexation constants
Stoichiometry of complexation
Selectivity of complexation
The binding sites
Supramolecular mechanism of complexation
On the lack of the Pirkle-type CSPs in TLC
Separation of Diastereoisomers by Means of TLC; V. Coman
Diastereoisomers
Non-chiral TLC systems used for diastereoisomer separation
Optimization of diastereoisomer separation by derivatization
Overview on diastereoisomer separation by TLC
Selected Bottle Necks of Densitometric Detection with Chiral Analytes; M. Sajewicz and T. Kowalska
2-Arylpropionic acids; APAs and their spontaneous oscillatory transenantiomerization
Two-dimensional retention of the selected 2-arylpropionic acids; APAs on silica gel in the one-dimensional development run as evidence of its chirality
Chirality of Pharmaceutical Products; J. Krzek, J. Bojarski, I. Podolak, E. Leciejewicz-Ziemecka
Stereoselectivity of drugs
Drugs as chiral selectors
Chiral purity of drugs
Chiral Separation of the Selected β-Blockers; D. Agbaba, B.M. Ivković
Direct enantioseparation of adrenergic drugs using molecularly imprinted polymers
Direct resolution of adrenergic enantiomers by impregnated TLC with optical pure compound
Chiral counter ions as mobile phase additives in separation of adrenergic drugs
Chemical derivatization with pure chiral compounds
Chiral Separation of Amino Acid Enantiomers; W. Gołkiewicz and B. Polak
Separation of amino acid enatiomers on the commercial chiral plates
Separation of amino acid enatiomers on the impregnated plates with chiral reagent
Separation of amino acid enantiomers on the commercial plates with chiral reagent in mobile phase
Most popular chiral reagents used for derivatization of amino acid enantiomers
Chiral Separation of NSAIDs; R. Bhushan, J. Martens
Approach to enantioseparation
Preparation of plates impregnated with chiral selector
Chiral selectors and their choice
Applications
Separation mechanisms
Determination of Components in Selected Chiral Drugs; J. Krzek, I. Podolak, U. Hubicka, A. Kwiecień
Antibiotics
Other compounds
Chiral Separations Using Marfey’s Reagent; R. Bhushan, H. Brückner
Direct and indirect separation
Marfey´s reagent; MR
Chiral variants of MR
Separation mechanisms
Application and comparison with other derivatizing agents
Editorial Reviews
"Within Thin Layer Chromatography in Chiral Separations and Analysis the editors succeeded very well in producing a comprehensive, yet accessible, source of information, having won respected specialists in this field. It provides an excellent overview of the subject both in theoretical and practical aspects."
–Dr. W. Schwack, University of Hohenheim, in CAMAG Bibliography Service, April 2008
"In 15 chapters of the book, written by 24 authors (many with well recognized achievements in the analysis of chiral compounds), all important aspects of the separation and analysis of enantiomers by planar chromatography are covered . . . One advantage of this monograph is the extensive literature cited by the authors, and in most chapters the references contain the full titles of the articles cited . . . publication is very timely."
– Edward Soczewinski, in Journal of Chromatographic Science, 2008
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