Chiral Separations: Methods and Protocols

ISBN-13: 9781617373909 / Angielski / Miękka / 2010 / 432 str.

Gerald Gubitz; Martin G. Schmid; Gerald G. Bitz

Opis

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.

Recenzje

"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

Spis treści

Chiral Separation Principles: An Introduction Gerald Gübitz and Martin G. Schmid Separation of Enantiomers by Thin-Layer Chromatography: An Overview Kurt Günther, Peter Richter, and Klaus Möller 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 Spégel, 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 Gübitz, 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 Göran Pettersson Use of Chiral Crown Ethers in Capillary Electrophoresis Martin G. Schmid and Gerald Gübitz Chiral Separations by Capillary Electrophoresis Using Cinchona Alkaloid Derivatives as Chiral Counter-Ions Michael Lämmerhofer 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 Sirén Chiral Ligand-Exchange Capillary Electrophoresis and Capillary Electrochromatography Martin G. Schmid and Gerald Gübitz 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 Spégel, Jakob Nilsson, and Staffan Nilsson Index

Blurb

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.