Comprehensive Chirality

1st Edition

Editor-in-Chiefs: Hisashi Yamamoto Erick Carreira
Hardcover ISBN: 9780080951676
eBook ISBN: 9780080951683
Imprint: Elsevier Science
Published Date: 5th September 2012
Page Count: 5648
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Although many books exist on the subject of chiral chemistry, they only briefly cover chiral synthesis and analysis as a minor part of a larger work, to date there are none that pull together the background information and latest advances in one comprehensive reference work. Comprehensive Chirality provides a complete overview of the field, and includes chiral research relevant to synthesis, analytic chemistry, catalysis, and pharmaceuticals. The individual chapters in each of the 9 volumes provide an in depth review and collection of references on definition, technology, applications and a guide/links to the related literature. Whether in an Academic or Corporate setting, these chapters will form an invaluable resource for advanced students/researchers new to an area and those who need further background or answers to a particular problem, particularly in the development of drugs.

Key Features

  • Chirality research today is a central theme in chemistry and biology and is growing in importance across a number of disciplinary boundaries. These studies do not always share a unique identifying factor or subject themselves to clear and concise definitions. This work unites the different areas of research and allows anyone working or researching in chiral chemistry to navigate through the most essential concepts with ease, saving them time and vastly improving their understanding.
  •  The field of chirality counts several journals that are directly and indirectly concerned with the field. There is no reference work that encompasses the entire field and unites the different areas of research through deep foundational reviews. Comprehensive Chirality fills this vacuum, and can be considered the definitive work. It will help users apply context to the diverse journal literature offering and aid them in identifying areas for further research and/or for solving problems.
  • Chief Editors, Hisashi Yamamoto (University of Chicago) and Erick Carreira (ETH Zürich) have assembled an impressive, world-class team of Volume Editors and Contributing Authors. Each chapter has been painstakingly reviewed and checked for consistent high quality. The result is an authoritative overview which ties the literature together and provides the user with a reliable background information and citation resource.


Graduate students and researchers working in organic, medicinal, and biological chemistry, as well as pharmacologists and toxicologists.

Table of Contents

Editors in Chief

Volume Editors


Permission Acknowledgments

Volume 1: Biological Significance: Pharmacology, Phamaceutical Agrochemical

1.1 Introduction: The Importance of Chirality in Drugs and Agrochemicals


1.1.1 Drugs

1.1.2 Agrochemicals


1.2 Importance of Chirality in the Field of Anti-infective Agents


1.2.1 Introduction

1.2.2 Antiinfectives from Natural Origin

1.2.3 Antiinfectives from Nonnatural Origin

1.2.4 Conclusion



1.3 Chirality in Antibacterial Agents


1.3.1 Introduction

1.3.2 Membrane Synthesis Inhibitors

1.3.3 Antibacterial Agents Acting on DNA

1.3.4 Protein Synthesis Inhibitors

1.3.5 Molecules Acting on New Targets

1.3.6 Antibacterial Agents as Chiral Selectors


1.4 Diastereomers, Enantiomers and Bioactivity. TMC207: A New Candidate for the Treatment of Tuberculosis


1.4.1 Introduction

1.4.2 Inhibition of ATP Synthase by TMC207

1.4.3 Chemistry

1.4.4 In Vitro Antimycobacterial Activity of TMC207

1.4.5 Conformational Analysis of TMC207

1.4.6 Molecular Basis and Stereospecificity

1.4.7 Conclusion



1.5 Fluorine in Medicinal Chemistry: Importance of Chirality

1.5.1 Introduction

1.5.2 Pharmaceuticals and Molecules of Biological Interest Bearing Fluorine and Trifluoromethyl Groups at an sp3-Hybridized Carbon


1.6 Peptides and Chirality Effects on the Conformation and the Synthesis of Medicinally Relevant Peptides


1.6.1 Introduction

1.6.2 Chirality in Peptides from Amino Acids to Secondary Structures

1.6.3 Chirality in Peptide Turn Geometry and Nucleation of &#946


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About the Editor-in-Chief

Hisashi Yamamoto

Chemists' ability to perform syntheses on a routine basis is due in large part to the development of new methods for synthesizing organic molecules which would have been impossible just a few decades ago. The availability of such new methods of synthesis has increased not only the range of structures which can be assembled but also the ease and economy of synthesis. During the past 30 years of his research, Professor Hisashi Yamamoto has had a tremendous impact on the field of organic chemistry through his reports of dramatic new advances in organic synthesis. Yamamoto's publications are numerous (over 450), and almost every one of them has provided an innovative new development or idea. Applications of this original and versatile chemistry have allowed him and other scientists to realize truly efficient syntheses of organic molecules of both theoretical and practical importance.

Hisashi Yamamoto has uncovered novel aspects of Lewis and Brønsted acid catalysts in selective organic synthesis. During his career he has discovered a wide variety of powerful new synthetic reactions, reagents, and catalysts based on acid catalysis chemistry. Through his dedicated efforts, Lewis and Brønsted acid are now recognized as major tools in the synthesis of both simple and complex organic molecules. Among Yamamoto's many superb contributions the following are especially worthy of mention.

His research in the area of organoaluminum chemistry has had a great impact on synthetic organic chemistry. The strong Lewis acidity of organoaluminum compounds appears to account for their strong tendency to form a stable 1:1 complex. Thus, the coordination of molecules invariably causes a change of reactivity, and the coordinated group may be activated or deactivated depending upon the type of reaction. Furthermore, with coordination of organic molecules an auxiliary bond can become coupled to the reagent and promote the desired reaction. In short, the reagents make a com

Affiliations and Expertise

The University of Chicago, Illinois, USA, Chubu University, Aichi, Japan

Erick Carreira

Erick M. Carreira was born in Havana, Cuba in 1963. He obtained a B.S. degree in 1984 from the University of Illinois at Urbana­Champaign under the supervision of Scott E. Denmark and a Ph.D. degree in 1990 from Harvard University under the supervision of David A. Evans. After carrying out postdoctoral work with Peter Dervan at the California Institute of Technology through late 1992, he joined the faculty at the same institution as an assistant professor of chemistry and subsequently was promoted to the rank of associate professor of chemistry in the Spring of 1996, and full professor in Spring 1997. Since September 1998, he has been full professor of Organic Chemistry at the ETH Zürich. He is the recipient of the American Chemical Society Award in Pure Chemistry, Nobel Laureate Signature Award, Fresenius Award, a David and Lucile Packard Foundation Fellowship in Science, Alfred P. Sloan Fellowship, Camille and Henry Dreyfus Teacher Scholar Award, Merck Young Investigator Award, Eli Lilly Young Investigator Award, Pfizer Research Award, National Science Foundation CAREER Award, Arnold and Mabel Beckman Young Investigator Award, and a Camille and Henry Dreyfus New Faculty Award. He is also the recipient of the Associated Students of the California Institute of Technology Annual Award in Teaching and a Richard M. Badger Award in Teaching.

His research program focuses on the asymmetric synthesis of biologically active, stereochemically complex, natural products. Target molecules are selected which pose unique challenges in asymmetric bond construction. A complex multistep synthesis endeavor provides a goal-oriented setting within which to engage in reaction innovation and design. Drawing from the areas of organometallic chemistry, coordination chemistry, and molecular recognition, Carreira's group is developing catalytic and stoichiometric reagents for asymmetric stereocontrol.

Affiliations and Expertise

ETH Zürich, Switzerland