Chiral Separations

Chiral Separations : Methods and Protocols

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Many compounds of biological and pharmacological interest are as- metric and show optical activity. Approximately 40% of the drugs in use are known to be chiral and only about 25% are administered as pure enantiomers. It is well established that the pharmacological activity is mostly restricted to one of the enantiomers (eutomer). In several cases, unwanted side effects or even toxic effects may occur with the inactive enantiomer (distomer). Even if the side effects are not that drastic, the inactive enantiomer has to be meta- lized, which represents an unnecessary burden for the organism. The admin- tration of pure, pharmacologically active enantiomers is therefore of great importance. The ideal way to get to pure enantiomers would be by enantioselective synthesis. However, this approach is usually expensive and not often practicable. Usually, the racemates are obtained in a synthesis, and the separation of the enantiomers on a preparative scale is necessary.
On the other hand, there is also a great demand for methods of enantiomer separation on an analytical scale for controlling synthesis, checking for racemization p- cesses, controlling enantiomeric purity, and for pharmacokinetic studies. C- ventional methods for enantiomer separation on a preparative scale are fractionated crystallization, the formation of diastereomeric pairs followed by repeated recrystallization, and enzymatic procedures. In recent years, ch- matographic methods such as gas chromatography and, especially, liquid ch- matography have attracted increasing interest for chiral separation, both on analytical and preparative scales.
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Product details

  • Hardback | 432 pages
  • 156 x 230 x 32mm | 821.02g
  • Humana Press Inc.
  • Totowa, NJ, United States
  • English
  • 2004 ed.
  • XIV, 432 p.
  • 1588291502
  • 9781588291509

Back cover copy

Methods for enantiomer separation are very important for controlling synthesis, for checking racemization, for enantiomeric purity control, and for pharmacokinetic studies. In Chiral Separations: Methods and Protocols, prominent experts from around the world detail the chromatographic and electroseparation techniques they have developed for chiral separations on an analytical scale. Described in step-by-step detail to ensure successful experimental results, the procedures are presented as either general methods or as specific applications to substance classes and special compounds, with emphasis on high performance liquid chromatography and capillary electrophoresis techniques, but also including thin layer chromotogrphic, gas chromatographic, and supercritical fluid chromatographic as well as recent electrochromotographic techniques. Each fully tested protocol includes an introduction to the principle underlying the method, equipment and reagent lists, and helpful notes on troubleshooting and avoiding known pitfalls.
Up-to-date and highly practical, Chiral Separations: Methods and Protocols will help both novice and advanced users not only choose optimal methods for their separation problems, but also readily obtain successful results.
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Review quote

"It is an excellent book, and can be recommended for every laboratory involved in the synthesis and analysis of chiral compounds. Moreover, the editors have succeeded in getting internationally known leading experts to write the contributions." -Angewandte Chemie

"...will undoubtedly be of value to those who need to find useful ways to carry out such separations." -Journal of Medicinal Chemistry

"...this book is a useful compendium of chiral methods and will be of use to many workers in the field." - Biomed Chronatogr
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Table of contents

Chiral Separation Principles: An Introduction
Gerald Gubitz and Martin G. Schmid

Separation of Enantiomers by Thin-Layer Chromatography: An Overview
Kurt Gunther, Peter Richter, and Klaus Moeller

Cyclodextrin-Based Chiral Stationary Phases for Liquid Chromatography: A Twenty-Year Overview
Clifford R. Mitchell and Daniel W. Armstrong

Enantiomeric Separations by HPLC Using Macrocyclic Glycopeptide-Based Chiral Stationary Phases: An Overview
Tom Ling Xiao and Daniel W. Armstrong

Chiral Separation by HPLC Using Polysaccharide-Based Chiral Stationary Phases
Chiyo Yamamoto and Yoshio Okamoto

Applications of Polysaccharide-Based Chiral Stationary Phases for Resolution of Different Compound Classes
Hassan Y. Aboul-Enein and Imran Ali

Chiral Separation by HPLC With Pirkle-Type Chiral Stationary Phases
Myung Ho Hyun and Yoon Jae Cho

Chiral Separation by HPLC Using the Ligand-Exchange Principle
Vadim A. Davankov

Chiral Separations by HPLC Using Molecularly Imprinted Polymers
Peter Spegel, Lars I. Andersson, and Staffan Nilsson

Indirect Enantioseparation by HPLC Using Chiral Benzofurazan-Bearing Reagents
Toshimasa Toyo'oka

Separation of the Racemic Trans-Stilbene Oxide by Sub-/Supercritical Fluid Chromatography
Leo Hsu, Genevieve Kennedy, and Gerald Terfloth

Chiral Separations Using Macrocyclic Antibiotics in Capillary Electrophoresis
Timothy J. Ward and Colette M. Rabai

Enantioresolutions by Capillary Electrophoresis Using Glycopeptide Antibiotics
Salvatore Fanali

Separation of Enantiomers by Capillary Electrophoresis Using Cyclodextrins
Wioleta Maruszak, Martin G. Schmid, Gerald Gubitz, Elzbieta Ekiert, and Marek Trojanowicz

Chiral Separations by Capillary Electrophoresis Using Proteins as Chiral Selectors
Jun Haginaka

Cellulases asChiral Selectors in Capillary Electrophoresis
Gunnar Johansson, Roland Isaksson, and Goeran Pettersson

Use of Chiral Crown Ethers in Capillary Electrophoresis
Martin G. Schmid and Gerald Gubitz

Chiral Separations by Capillary Electrophoresis Using Cinchona Alkaloid Derivatives as Chiral Counter-Ions
Michael Lammerhofer and Wolfgang Lindner

Chiral Separation by Capillary Electrophoresis Using Polysaccharides
Hiroyuki Nishi

Chiral Micellar Electrokinetic Chromatography
Koji Otsuka and Shigeru Terabe

Chiral Separation by Capillary Electrophoresis in Nonaqueous Medium
Marja-Liisa Riekkola and Heli Siren

Chiral Ligand-Exchange Capillary Electrophoresis and Capillary Electrochromatography
Martin G. Schmid and Gerald Gubitz

Enantioseparation in Capillary Chromatography and Capillary Electrochromatography Using Polysaccharide-Type Chiral Stationary Phases
Bezhan Chankvetadze

Chiral Separation by Capillary Electrochromatography Using Cyclodextrin Phases
Dorothee Wistuba, Jingwu Kang, and Volker Schurig

Chiral Separations by Capillary Electrochromatography Using Molecularly Imprinted Polymers
Peter Spegel, Jakob Nilsson, and Staffan Nilsson

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