Organic Stereochemistry Guiding Principles and Biomedicinal Relevance

This book should become an indispensable asset on the bookshelves of pharmaceutical laboratories in academia and in industry, as well as of laboratories devoted to plant protection. Furthermore, for teachers in this area it will not only be a useful compilation of the various languages and definitions of organic stereochemistry, but also a welcome source of examples for demonstrating to their students the intricate and intriguing role stereochemistry plays in the chemistry of life. This textbook presents the molecular scale of matter in the broad diversity and richness of its three dimensions, giving due attention when relevant to the temporal dimension in which molecules exist, act, and react. The focus is on two significant fields of three-dimensional chemistry: a presentation of the guiding principles in organic stereochemistry, followed by a focus on the biochemical and medicinal relevance of this discipline. The treatment of Guiding Principles gives priority to didactic clarity and nomenclature issues, as detailed and illustrated in Parts 1 to 4: Symmetry Elements and Operations, Classification of Stereoisomers, Stereoisomerism Resulting from One or Several Stereogenic Centers, Other Stereogenic Elements: Axes of Chirality, Planes of Chirality, Helicity, and (E,Z)-Diastereoisomerism, Isomerisms about Single Bonds and in Cyclic Systems. This is followed by Parts 5 to 8 which focus on the biomedicinal relevance of stereochemistry, with special reference to the biochemistry and pharmacology of medicinal compounds. Here, examples and applications are discussed and illustrated based on their relevance to a given specific stereochemical aspect: Chirality in Molecular and Clinical Pharmacology, The Conformational Factor in Molecular Pharmacology, The Concept of Substrate Stereoselectivity in Biochemistry and Xenobiotic Metabolism, Prostereoisomerism and the Concept of Product Stereoselectivity in Xenobiotic Metabolism. Finally, the book contains a gift for broad-minded readers with an interest in the historical roots of stereochemistry: Part 9: Molecular Chirality in Chemistry and Biology: Historical Milestones.