Enantioselective Synthesis Enantiomeric Separations And Chiral Recognition
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Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition by Maria Elizabeth Tiritan,Madalena Pinto ,Carla Sofia Garcia Fernandes Pdf
This book includes both fundamental studies and applications in a multidisciplinary research field involving a high diversity of chiral compounds, including commercial substances with industrial applications, pharmaceuticals, and new chiral compounds with promising biological activities.
Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition by Maria Elizabeth Tiritan,Madalena Pinto,Carla Sofia Garcia Fernandes Pdf
This book includes both fundamental studies and applications in a multidisciplinary research field involving a high diversity of chiral compounds, including commercial substances with industrial applications, pharmaceuticals, and new chiral compounds with promising biological activities. Recent developments and innovative approaches to producing enantiomerically pure compounds of industrial and research interest are included. Enantiomeric separation in both the analytical and preparative scale, determination of the enantiomeric purity, insights into enantioselective synthesis and many different aspects of chiral recognition, including chiral sensors, recognition in biological systems, and in analytical methods, are presented. Original research and review articles show the broad scope of chirality in diverse analytical fields and the connection to enantioselective synthesis and biological activities.
In spite of important advances in asymmetric synthesis, chiral compounds cannot all be obtained in a pure state by asymmetric synthesis. As a result, enantiomer separation remains an important technique for obtaining optically active materials. Although asymmetric synthesis is a once-only procedure, an enantiomer separation process can be repeated until the optically pure sample is obtained. This book discusses several new enantiomer separation methods using modern techniques developed by experts in the field. These methods consist mainly of the following three types: 1) Enantiomer separation by inclusion complexation with a chiral host compound 2) Enantiomer separation using biological methods 3) Enantiomer separation by HPLC chromatography using a column containing a chiral stationary phase. Separation of a racemic compound has been called “optical resolution” or simply “resolution”. Nowadays, the descriptions “enantiomer resolution” or “enantiomer separation” are also commonly used. Accordingly, “Enantiomer Separation” is used in the title of this book. The editor and all chapter contributors hope that this book is helpful for scientists and engineers working in this field.
Chiral Recognition in Separation Methods by Alain Berthod Pdf
What drives a scientist to edit a book on a speci c scienti c subject such as chiral mechanisms in separation methods? Until December 2005, the journal Analytical Chemistry of the American Chemical Society (Washington, DC) had an A-page section that was dedicated to simple and clear presentations of the most recent te- niques or the state of the art in a particular eld or topic. The “A-page” section was prepared for a broad audience of chemists including industrial professionals, s- dents as well as academics looking for information outside their eld of expertise. 1 Daniel W. Armstrong, one of the editors of this journal and a twenty-year+ long friend, invited me to present my view on chiral recognition mechanisms in a simple and clear way in an “A-page” article. In 2006, the “A-page” section was maintained as the rst articles at the beginning of each rst bi-monthly issue but the pagination was no longer page distinguished from the regular research articles published by the journal. During the time between the invitation and the submission, the A-page section was integrated into the rest of the journal and the article appeared as (2006) Anal Chem (78):2093–2099.
Asymmetric Synthesis, Volume 1: Analytical Methods covers the major analytical methods used to determine enantiomeric ratios. This volume contains chapters that discuss the methods used to obtain chiral compounds and shows how to evaluate the chiral efficiency of an asymmetric synthesis. Analytical methods such as polarimetry, competitive reaction methods, isotope dilution, gas and liquid chromatography, and nuclear magnetic resonance methods are also discussed. Chemists and researchers in the field of pharmaceutical will find the book very useful.
Chiral Separation Techniques by G. Subramanian Pdf
This is a completely revised and updated sequel to 'A Practical Approach to Chiral Separations by Liquid Chromatography' by the same editor. The scope has been extended to further chiral separation techniques like electrophoresis, membrane separations, or biological assays. More emphasis is put on preparative separation techniques. From reviews of the previous edition: 'A team of experts from academic and industrial laboratories throughout the world have compiled their findings and experience to make this book an exceptionally timely and unique contribution to the field' European Journal of Drug Metabolism 'The dense mass of information contained in this book will make it a valuable resource ...' Chemical Engineering Research '... this is a worthwhile addition to the expanding chiral literature and the book should be of value to those working in this field' The Analyst
Enantioselective Synthesis of Beta-Amino Acids by Eusebio Juaristi,Vadim A. Soloshonok Pdf
Covers all facets of the synthesis of ß-amino acids As evidenced by an exponential increase in the literature published on the subject, interest in ß-amino acids has grown over the past several years. With major pharmaceutical applications, these amino acids are now studied across multiple lines of research, including combinatorial chemistry, medicinal chemistry, molecular design, proteomics, and others. This Second Edition of Enantioselective Synthesis of ß-Amino Acids updates reviews included in the First Edition while also covering new developments since its publication. The book presents detailed discussions of the most important methods for the synthesis of ß-amino acids. In most cases, the lead chemist who originally developed a method provides an authoritative description of it. In addition, Enantioselective Synthesis of ß-Amino Acids, Second Edition: * Features introductory overviews on the structural types of relevant ß-amino acid targets and salient ß-amino acids present in natural products * Dedicates several chapters to advances in the synthesis of oligomers from ß-amino acids * Includes general and practical procedures for the preparation of ß-amino acids in each chapter * Discusses the most important methods that have been recently developed for the asymmetric synthesis of cyclic and open-chain ß-amino acids * Includes a report on the preparation of libraries of enantiopure ß-amino acids using combinatorial approaches The only book of its kind available today, Enantioselective Synthesis of ß-Amino Acids, Second Edition offers upper-level students and professionals an essential resource for pharmaceutical development, medicinal chemistry, and biochemistry.
In one handy volume this handbook summarizes the most common synthetic methods for the separation of racemic mixtures, allowing an easy comparison of the different strategies described in the literature. Alongside classical methods, the authors also consider kinetic resolutions, dynamic kinetic resolutions, divergent reactions of a racemic mixture, and a number of "neglected" cases not covered elsewhere, such as the use of circularly polarized light, polymerizations, "ripening" processes, dynamic combinatorial chemistry, and several thermodynamic processes. The result is a thorough introduction to the field plus a long-needed, up-to-date overview of the chemical, biological, and physical methods and their applications. Newcomers to the field, students as well as experienced synthetic chemists will benefit from the highly didactic presentation: Every method is presented in detail, from relatively simple separation problems to advanced complex resolution methods.
Preparative Enantioselective Chromatography by Geoffrey B. Cox Pdf
The development of chiral liquid chromatography, facilitating thestraightforward separation of enantiomers, was a significantadvance in chromatography, leading to widespread application inanalytical chemistry. Application in preparative chromatography hasbeen less rapid, but with the development of single enantiomerpharmaceuticals its use is increasingly common in chemicalsynthesis at laboratory, pilot plant and even full productionscale. Brings non-experts up to speed quickly and comprehensively,facilitating the rapid development of effective separations ofenantiomeric mixtures on a range of process scales Presents case studies drawn from within the pharmaceuticalindustry to clearly illustrate the utility and value of preparativescale enantioselective chromatography in chemical research,development and production Key reference source and entry to the literature so the readerdoes not have to engage in expensive and time consuming literaturesearching
Asymmetric Synthesis by Alan Aitken,S. N. Kilenyi Pdf
Asymmetric synthesis is one of the most important areas of research and development in synthetic organic chemistry, and has wide-ranging industrial applications. This introduction to the subject covers chirality, nomenclature and analytical methods of resolution. The main body of the text describes the principal methods available to the organic chemist wishing to synthesize chiral compounds. Case studies are included, and reference sections allow access to the relevant review and research literature. This book is written for organic chemists at postgraduate and advanced undergraduate level.
While working as a chromatographer in the pharmaceutical industry, it became apparent to the editor that there was a pressing need for a comprehensive reference text for analysts working on the resolution of enantiomers by liquid chromatography (LC). This need arises from the fact that, whereas previously it was very difficult to determine enantiomers by direct means, there is now a wide choice of direct LC methods. At the same time, regulatory authorities have been changing their attitudes towards the administration of pharmaceuticals as racemates, partly because it is now possible to study the individual enantiomers. Clearly this abundance of new information needs to be rationalized. More importantly, the chiral LC systems which are commercially available or readily accessible to the practising chromatographer needed to be reviewed and, to a much greater extent than in existing reviews or books, discussed in terms of their practical application. Accordingly this book is very much orientated towards the practical aspects of these commercially available and readily accessible chiral LC systems. To this end, it is written for practising chromatographers by a team of practising, experienced chromatographers who have spent many years tackling the problems presented by resolving enantiomers by LC. The practical aspects of common chiral LC systems cannot be fully understood if discussed in isolation.
Chirality in Drug Research by Eric Francotte,Wolfgang Lindner Pdf
Divided into the three main sections of synthesis, analysis and drug development, this handbook covers all stages of the drug development process, including large-scale synthesis and purification of chirally pure pharmaceuticals. The two editors from academia and a major pharmaceutical company have assembled an experienced, international team who provide first-hand practical advice and report previously unpublished data. In the first section, the isolation of chiral drugs from natural sources, their production in enzymatic processes and the resolution of racemic mixtures in preparative chromatography are outlined in separate chapters. For the section on qualitative and quantitative analysis, enantioselective chromatographic methods are presented as well as optical methods and CE-MS, while the final section deals with the pharmacology, pharmacokinetics and metabolic aspects of chiral drugs, devoting whole chapters to stereoselective drug binding and modeling chiral drug-receptor interactions. With its unique industry-relevant aspects, this is a must for medicinal and pharmaceutical chemists.
Principles of Asymmetric Synthesis by R.E. Gawley,J. Aubé Pdf
The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis (more than 1300 references), the aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions. It is important to note that the references were each individually checked by the authors to verify relevance to the topics under discussion. The study of stereoselectivity has evolved from issues of diastereoselectivity, through auxiliary-based methods for the synthesis of enantiomerically pure compounds (diastereoselectivity followed by separation and auxiliary cleavage), to asymmetric catalysis. In the latter instance, enantiomers (not diastereomers) are the products, and highly selective reactions and modern purification techniques allow preparation - in a single step - of chiral substances in 99% ee for many reaction types. After an explanation of the basic physical-organic principles of stereoselectivity, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Analytical Methods" provides a critical overview of the most common methods for analysis of stereoisomers. The authors then follow the 'tried-and-true' format of grouping the material by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions (enolate alkylations, organometal additions to carbonyls, aldol and Michael reactions, and cycloadditions and rearrangements), one chapter on reductions and hydroborations (carbon-hydrogen bond forming reactions), and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). Leading references are provided to natural product synthesis that have been accomplished using a given reaction as a key step. In addition to tables of examples that show high selectivity, a transition state analysis is presented to explain - to the current level of understanding - the stereoselectivity of each reaction. In one case (Cram's rule) the evolution of the current theory is detailed from its first tentative (1952) postulate to the current Felkin-Anh-Heathcock formalism. For other reactions, only the currently accepted rationale is presented. Examination of these rationales also exposes the weaknesses of current theories, in that they cannot always explain the experimental observations. These shortcomings provide a challenge for future mechanistic investigations.
Chromatographic Enantioseparation by Stig G. Allenmark Pdf
Allenmark (microbiological chemistry, U. of Gothenburg) gives a thorough treatment of chiral chromatography, covering basic theory, methods (particularly stationary phase design), and applications. Treatment is self-contatined; early chapters explain principles, incorporating background material on organic stereochemistry; later ones cover instrumentation, preparation, synthesis, and analysis. Includes in-depth coverage of liquid chromatographic methods and discussion of industrial uses for large-scale preparative resolutions, including column sample capacity, chromatographic reproducability, and automatic operation. Acidic paper. Annotation copyrighted by Book News, Inc., Portland, OR
