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. I am convinced that studying this book will be an eye-opener for many scientists in the field of life sciences. 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." - Prof. Dr. Dieter Seebach, Laboratory of Organic Chemistry, ETH Zurich, Switzerland



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:

'Molecular Chirality in Chemistry and Biology: Historical Milestones'


Key features:

* Consists entirely of beautifully produced colored figures
* Includes marginal notes, giving clear-cut short definitions of terms used in the corresponding caption
* Provides an alphabetic glossary of terms
* Offers an extensive index

Bernard Testa is Emeritus Professor of the University of Lausanne, having served there for 25 years as a full professor of medicinal chemistry. He has written 6 books and edited 33 others, and (co)-authored well over 450 research and review articles in the fields of drug design and drug metabolism. Between 1994 and 1998, he was the European Editor of Pharmaceutical Research, and is now a Senior Editor of Chemistry & Biodiversity, as well as serving on the editorial boards of several leading journals. Professor Testa holds honorary doctorates from the universities of Milan, Montpellier, and Parma, and is a recipient of the Nauta Award on Pharmacochemistry given by the European Federation for Medicinal Chemistry.

John Caldwell trained in biochemical pharmacology at St. Mary's Hospital Medical School in London, where he held various academic positions from 1972, becoming a full professor in 1987 and Dean of the Medical School in 1995. After St. Mary's merger with Imperial College in 1997, he served as the head of Biomedical Sciences and head of the Medical School. In 2002 he moved to the University of Liverpool to become Dean of the Faculty of Medicine and, additionally, a Pro-Vice-Chancellor in 2007. He stepped down as Dean in 2010 and continues on as a Pro-Vice-Chancellor. He is particularly well known for his investigations of the importance of the application of stereochemistry to the development of more effective drugs. He founded the interdisciplinary journal Chirality in 1989 and remains as Editor-in-Chief. Among many honours and distinctions, he has been the president of the International Society for the Study of Xenobiotics and the Sterling-Winthrop Distinguished Professor at the University of Michigan. He became an honorary member of the Royal College of Physicians in 1998. He is a board member of a number of companies and serves at director level in the UK National Health Service.

M. Volkan Kisakurek received his Ph.D. in Organic Chemistry at the University of Zurich. For over 32 years, he has been holding the positions of the Editor-in-Chief of Helvetica Chimica Acta and Managing Director of the corresponding publishing house. For more than 20 years, he actively participated in the IUPAC Commission for Nomenclature.

Foreword: D. Seebach

Preface: The Editors

Part 1: Symmetry Elements and Operations, Classification of Stereoisomers (B. Testa, G. Vistoli, and A. Pedretti)

Part 2: Stereoisomerism Resulting from One or Several Stereogenic Centers (B. Testa)

Part 3: Other Stereogenic Elements: Axes of Chirality, Planes of Chirality, Helicity, and (E,Z)-Diastereoisomerism (B. Testa)

Part 4: Isomerisms about Single Bonds and in Cyclic Systems (B. Testa, G. Vistoli, and A. Pedretti)

Part 5: Stereoselectivity in Molecular and Clinical Pharmacology (B. Testa, G. Vistoli, A. Pedretti, and J. Caldwell)

Part 6: The Conformation Factor in Molecular Pharmacology (G. Vistoli, B. Testa, and A. Pedretti)

Part 7: The Concept of Substrate Stereoselectivity in Biochemistry and Xenobiotic Metabolism (B. Testa)

Part 8: Prostereoisomerism and the Concept of Product Stereoselectivity in Biochemistry and Xenobiotic Metabolism (B. Testa)

Part 9: Molecular Chirality in Chemistry and Biology: Historical Milestones (J. Gal)

Glossary

Index