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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 physics and chemistry to the organisms and structures that we see and use in our everyday life. The…mehr
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 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 communication * Many illustrations, chemical structures, and photographs that enable the reader to connect the actual asymmetrical structures to the different phenomena that depend on structural asymmetry In 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.
JAMES P. RIEHL received a BS degree in chemistry from Villanova University in 1970 and a PhD in physical chemistry from Purdue University in 1975. He is currently Dean of the Swenson College of Science and Engineering and Professor of Chemistry at the University of Minnesota Duluth, a position he has held since 2000. Dr. Riehl is a frequent invited speaker nationally and internationally on the topic of molecular chirality, and is the author of numerous research publications in the applications of optical spectroscopy to the study of chiral structures. He was the recipient of the St. Louis Award of the American Chemical Society for his outstanding contributions to the chemistry profession, and currently holds a University of Minnesota McKnight Presidential Leadership Chair.
Inhaltsangabe
Preface xi List of Figures and Biographic Photographs xv 1 The Mirror Image 1 Handedness 2 The Symmetry of Nonsuperimposable Mirror Images 5 Nomenclature for Chiral Molecules 11 Nomenclature for Dissymmetric and Other Chiral Molecules 19 Summary 24 Suggestions for Further Reading 24 References 25 List of Biographic Photographs, Sidebars, and Figures 25 2 Molecular Chirality in Living Systems 27 Optical Rotation 30 From Biot to Pasteur 36 Biochemical Homochirality 44 Determination of Absolute Structures of Chiral Molecules 52 Summary 54 Suggestions for Further Reading 55 References 55 List of Biographic Photographs, Sidebars, and Figures 56 3 The Origin of Chirality in Living Systems 59 Must Life be Chiral? 60 Mirror-image life? 62 The Origin of Homochirality in Living Systems 63 Extraterrestrial Chirality 65 Nuclear Chirality 70 Other Extraterrestrial Sources 72 The Beginning of Life on Earth: Biochemistry 73 Getting Started in the Right (or Left) Direction 76 Summary 78 Suggestions for Further Reading 78 References 79 List of Sidebars and Figures 80 4 Chiral Chemistry, Recognition, and Control in Living Systems 81 Chiral Chemical Evolution 81 Chiral Recognition at the Molecular Level 83 Examples of Chiral Recognition and Discrimination 87 Smell 87 Taste 91 Communication 93 Chirality as a Control Mechanism in Biochemistry 104 Summary 108 Suggestions for Further Reading 108 References 108 List of Biographic Photographs, Sidebars, and Figures 110 5 Chirality and Drugs 111 Chirality in Natural Remedies and Folk Medicines 112 Enantiomeric Differences in Natural Products 114 Thalidomide and Regulation of Chiral Drugs 118 Chirality and Drug Activity 121 Ibuprofen 121 Prozac 122 Cialis 123 Nexium 125 Lipitor 128 Chiral Switching 129 Ephedrine, Pseudoephedrine, and Methamphetamine 131 Preparation of Pure Enantiomers 135 Summary 143 Suggestions for Further Reading 143 References 143 List of Biographic Photographs, Sidebars, and Figures 145 6 The Chirality of Living Systems 147 Preliminary Cautions 148 Chirality in Nature 153 Classification of Plant and Animal Chirality (Asymmetry) 159 Symmetric Life 160 Racemic Life 160 Asymmetric Life 162 Homo sapiens Asymmetry 170 Summary 171 Suggestions for Further Reading 171 References 172 List of Sidebars and Figures 173 7 The Handedness of Homo sapiens 175 Are You Right-Handed or Left-Handed? 176 The Statistics of Handedness 178 The Origin of Left-Handedness 183 The Human Genetics of Handedness 186 Summary 192 Suggestions for Further Reading 193 References 194 List of Sidebars and Figures 195 8 Living in a Right-Hander's World 197 Clockwise and Counterclockwise (or Anticlockwise) Rotation 198 Helical Stairways 201 Around the House 204 Making Music Left-Handed 205 The Chirality of Writing 207 Sports and the Left-Hander 210 American Baseball: The Chiral Sport 216 Driving on the Left or Right Side 221 Windmills 224 Summary 227 Suggestions for Further Reading 228 References 228 List of Sidebars and Figures 228 9 The Asymmetric Universe 231 List of Figures 234 Appendix 235 Biography 239 Index 241
Chapter 1: The Mirror Image.. Chapter 2: Molecular Chirality in Living Systems.. Chapter 3: The Origin of Chirality of Living Systems.. Chapter 4: Chiral Chemistry, Recognition and Control.. Chapter 5: Chirality and Drugs.. Chapter 6: The Chirality of Licing Things.. Chapter 7: The Handedness of Homo sapiens.. Chapter 8: Living in a right-handers worlds.. Chapter 9: The Asymmetric Universe. Appendix I: A primer on interpreting molecular structure drawings.. Index..
Preface xi List of Figures and Biographic Photographs xv 1 The Mirror Image 1 Handedness 2 The Symmetry of Nonsuperimposable Mirror Images 5 Nomenclature for Chiral Molecules 11 Nomenclature for Dissymmetric and Other Chiral Molecules 19 Summary 24 Suggestions for Further Reading 24 References 25 List of Biographic Photographs, Sidebars, and Figures 25 2 Molecular Chirality in Living Systems 27 Optical Rotation 30 From Biot to Pasteur 36 Biochemical Homochirality 44 Determination of Absolute Structures of Chiral Molecules 52 Summary 54 Suggestions for Further Reading 55 References 55 List of Biographic Photographs, Sidebars, and Figures 56 3 The Origin of Chirality in Living Systems 59 Must Life be Chiral? 60 Mirror-image life? 62 The Origin of Homochirality in Living Systems 63 Extraterrestrial Chirality 65 Nuclear Chirality 70 Other Extraterrestrial Sources 72 The Beginning of Life on Earth: Biochemistry 73 Getting Started in the Right (or Left) Direction 76 Summary 78 Suggestions for Further Reading 78 References 79 List of Sidebars and Figures 80 4 Chiral Chemistry, Recognition, and Control in Living Systems 81 Chiral Chemical Evolution 81 Chiral Recognition at the Molecular Level 83 Examples of Chiral Recognition and Discrimination 87 Smell 87 Taste 91 Communication 93 Chirality as a Control Mechanism in Biochemistry 104 Summary 108 Suggestions for Further Reading 108 References 108 List of Biographic Photographs, Sidebars, and Figures 110 5 Chirality and Drugs 111 Chirality in Natural Remedies and Folk Medicines 112 Enantiomeric Differences in Natural Products 114 Thalidomide and Regulation of Chiral Drugs 118 Chirality and Drug Activity 121 Ibuprofen 121 Prozac 122 Cialis 123 Nexium 125 Lipitor 128 Chiral Switching 129 Ephedrine, Pseudoephedrine, and Methamphetamine 131 Preparation of Pure Enantiomers 135 Summary 143 Suggestions for Further Reading 143 References 143 List of Biographic Photographs, Sidebars, and Figures 145 6 The Chirality of Living Systems 147 Preliminary Cautions 148 Chirality in Nature 153 Classification of Plant and Animal Chirality (Asymmetry) 159 Symmetric Life 160 Racemic Life 160 Asymmetric Life 162 Homo sapiens Asymmetry 170 Summary 171 Suggestions for Further Reading 171 References 172 List of Sidebars and Figures 173 7 The Handedness of Homo sapiens 175 Are You Right-Handed or Left-Handed? 176 The Statistics of Handedness 178 The Origin of Left-Handedness 183 The Human Genetics of Handedness 186 Summary 192 Suggestions for Further Reading 193 References 194 List of Sidebars and Figures 195 8 Living in a Right-Hander's World 197 Clockwise and Counterclockwise (or Anticlockwise) Rotation 198 Helical Stairways 201 Around the House 204 Making Music Left-Handed 205 The Chirality of Writing 207 Sports and the Left-Hander 210 American Baseball: The Chiral Sport 216 Driving on the Left or Right Side 221 Windmills 224 Summary 227 Suggestions for Further Reading 228 References 228 List of Sidebars and Figures 228 9 The Asymmetric Universe 231 List of Figures 234 Appendix 235 Biography 239 Index 241
Chapter 1: The Mirror Image.. Chapter 2: Molecular Chirality in Living Systems.. Chapter 3: The Origin of Chirality of Living Systems.. Chapter 4: Chiral Chemistry, Recognition and Control.. Chapter 5: Chirality and Drugs.. Chapter 6: The Chirality of Licing Things.. Chapter 7: The Handedness of Homo sapiens.. Chapter 8: Living in a right-handers worlds.. Chapter 9: The Asymmetric Universe. Appendix I: A primer on interpreting molecular structure drawings.. Index..
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