Mirror-Image Asymmetry: An Introduction to the Origin and Consequences of Chirality
An overview of the importance and consequences of asymmetry from molecules to the macroscopic world\ As scientists have become more capable of probing the structure of three-dimensional objects at the molecular level, the need to understand the concept and the consequences of mirror-image asymmetry—chirality—has increased enormously. Written at an introductory level, Mirror-Image Asymmetry provides an overview of the importance and effects of asymmetry from the atomic and molecular world of...
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An overview of the importance and consequences of asymmetry from molecules to the macroscopic worldAs scientists have become more capable of probing the structure of three-dimensional objects at the molecular level, the need to understand the concept and the consequences of mirror-image asymmetry—chirality—has increased enormously. Written at an introductory level, Mirror-Image Asymmetry provides an overview of the importance and effects of asymmetry from the atomic and molecular world of physics and chemistry to the organisms and structures that we see and use in our everyday life. The reader will develop a broad appreciation of three-dimensional asymmetry from the microscopic molecular world to the macroscopic world of handedness, automobile driving, windmills, sports, and similar phenomena. The book features:An introduction to basic definitions and the nomenclature of asymmetric and dissymmetric molecules Up-to-date examples of the importance and consequences of asymmetry in modern drug applications, current theories of the origin of asymmetry in nature, and examples of molecular asymmetry in smell, taste, and insect communicationMany illustrations, chemical structures, and photographs that enable the reader to connect the actual asymmetrical structures to the different phenomena that depend on structural asymmetryIn the 150 years since Louis Pasteur discovered asymmetry in molecular structures, scientists have made great progress in understanding how interactions between chiral molecules influence biochemical processes. This knowledge is leading to very sophisticated asymmetric synthetic techniques that have greatly benefitted many research groups especially those in the pharmaceutical industry. This guide to the role of molecular and macroscopic chirality will inspire students and scientists in chemistry, biology, physics, and drug discovery.
Preface xiList of Figures and Biographic Photographs xv1 The Mirror Image 1Handedness 2The Symmetry of Nonsuperimposable Mirror Images 5Nomenclature for Chiral Molecules 11Nomenclature for Dissymmetric and Other Chiral Molecules 19Summary 24Suggestions for Further Reading 24References 25List of Biographic Photographs, Sidebars, and Figures 252 Molecular Chirality in Living Systems 27Optical Rotation 30From Biot to Pasteur 36Biochemical Homochirality 44Determination of Absolute Structures of Chiral Molecules 52Summary 54Suggestions for Further Reading 55References 55List of Biographic Photographs, Sidebars, and Figures 563 The Origin of Chirality in Living Systems 59Must Life be Chiral? 60Mirror-Image Life? 62The Origin of Homochirality in Living Systems 63Extraterrestrial Chirality 65Nuclear Chirality 70Other Extraterrestrial Sources 72The Beginning of Life on Earth: Biochemistry 73Getting Started in the Right (or Left) Direction 76Summary 78Suggestions for Further Reading 78References 79List of Sidebars and Figures 804 Chiral Chemistry, Recognition, and Control in Living Systems 81Chiral Chemical Evolution 81Chiral Recognition at the molecular Level 83Examples of Chiral Recognition and Discrimination 87Smell 87Taste 91Communication 93Chirality as a Control mechanism in Biochemistry 104Summary 108Suggestions for Further Reading 108References 108List of Biographic Photographs, Sidebars, and Figures 1105 Chirality and Drugs 111Chirality in Natural Remedies and Folk Medicines 112Enantiomeric Differences in Natural Products 114Thalidomide and Regulation of Chiral Drugs 118Chirality and Drug Activity 121Ibuprofen 121Prozac 122Cialls 123Nexium 125Lipitor 128Chiral Switching 129Ephedrine, Pseudoephedrine, and Methamphetamine 131Preparation of Pure Enantiomers 135Summary 143Suggestions for Further Reading 143References 143List of Biographic Photographs, Sidebars, and Figures 1456 The Chirality of Living Systems 147Preliminary Cautions 148Chirality in Nature 153Classification of Plant and Animal Chirality (Asymmetry) 159Symmetric life 160Racemic Life 160Asymmetric Life 162Homo Sapiens Asymmetry 170Summary 171Suggestions for Further Reading 171References 172List of Sidebars and Figures 1737 The Handedness of Homo Sapiens 175Are You Right-Handed or Left-Handed? 176The Statistics of Handedness 178The Origin of Left-Handedness 183The Human Genetics of Handedness 186Summary 192Suggestions for Further Reading 193References 194List of Sidebars and Figures 1958 Living in a Right-Hander's World 197Clockwise and Counterclockwise (or Anticlockwise) Rotation 198Helical Stairways 201Around the House 204Making Music Left-Handed 205The Chirality of Writing 207Sports and the Left-Hander 210American Baseball: The Chiral Sport 216Driving on the Left or Right Side 221Windmills 224Summary 227Suggestions for Further Reading 228References 228List of Sidebars and Figures 2289 The Asymmetric Universe 231List of Figures 234Appendix 235Biography 239Index 241
\ From the Publisher"Riehl should be commended for presenting an understable introduction to chirality to such a wide audience." (Choice, October 2010).\ \ \
