Mirror-Image Asymmetry: An Introduction to the Origin and Consequences of Chirality

Cover......Page 1
CONTENTS......Page 10
PREFACE......Page 14
LIST OF FIGURES AND BIOGRAPHIC PHOTOGRAPHS......Page 18
1 THE MIRROR IMAGE......Page 24
HANDEDNESS......Page 25
THE SYMMETRY OF NONSUPERIMPOSABLE MIRROR IMAGES......Page 28
NOMENCLATURE FOR CHIRAL MOLECULES......Page 34
NOMENCLATURE FOR DISSYMMETRIC AND OTHER CHIRAL MOLECULES......Page 42
SUGGESTIONS FOR FURTHER READING......Page 47
LIST OF BIOGRAPHIC PHOTOGRAPHS, SIDEBARS, AND FIGURES......Page 48
2 MOLECULAR CHIRALITY IN LIVING SYSTEMS......Page 50
OPTICAL ROTATION......Page 53
FROM BIOT TO PASTEUR......Page 59
BIOCHEMICAL HOMOCHIRALITY......Page 67
DETERMINATION OF ABSOLUTE STRUCTURES OF CHIRAL MOLECULES......Page 75
SUMMARY......Page 77
REFERENCES......Page 78
LIST OF BIOGRAPHIC PHOTOGRAPHS, SIDEBARS, AND FIGURES......Page 79
3 THE ORIGIN OF CHIRALITY IN LIVING SYSTEMS......Page 82
MUST LIFE BE CHIRAL?......Page 83
MIRROR-IMAGE LIFE?......Page 85
THE ORIGIN OF HOMOCHIRALITY IN LIVING SYSTEMS......Page 86
EXTRATERRESTRIAL CHIRALITY......Page 88
NUCLEAR CHIRALITY......Page 93
OTHER EXTRATERRESTRIAL SOURCES......Page 95
THE BEGINNING OF LIFE ON EARTH: BIOCHEMISTRY......Page 96
GETTING STARTED IN THE RIGHT (OR LEFT) DIRECTION......Page 99
SUGGESTIONS FOR FURTHER READING......Page 101
REFERENCES......Page 102
LIST OF SIDEBARS AND FIGURES......Page 103
CHIRAL CHEMICAL EVOLUTION......Page 104
CHIRAL RECOGNITION AT THE MOLECULAR LEVEL......Page 106
SMELL......Page 110
TASTE......Page 114
COMMUNICATION......Page 116
CHIRALITY AS A CONTROL MECHANISM IN BIOCHEMISTRY......Page 127
REFERENCES......Page 131
LIST OF BIOGRAPHIC PHOTOGRAPHS, SIDEBARS, AND FIGURES......Page 133
5 CHIRALITY AND DRUGS......Page 134
CHIRALITY IN NATURAL REMEDIES AND FOLK MEDICINES......Page 135
ENANTIOMERIC DIFFERENCES IN NATURAL PRODUCTS......Page 137
THALIDOMIDE AND REGULATION OF CHIRAL DRUGS......Page 141
IBUPROFEN......Page 144
PROZAC......Page 145
CIALIS......Page 146
NEXIUM......Page 148
LIPITOR......Page 151
CHIRAL SWITCHING......Page 152
EPHEDRINE, PSEUDOEPHEDRINE, AND METHAMPHETAMINE......Page 154
PREPARATION OF PURE ENANTIOMERS......Page 158
REFERENCES......Page 166
LIST OF BIOGRAPHIC PHOTOGRAPHS, SIDEBARS, AND FIGURES......Page 168
6 THE CHIRALITY OF LIVING SYSTEMS......Page 170
PRELIMINARY CAUTIONS......Page 171
CHIRALITY IN NATURE......Page 176
CLASSIFICATION OF PLANT AND ANIMAL CHIRALITY (ASYMMETRY)......Page 182
RACEMIC LIFE......Page 183
ASYMMETRIC LIFE......Page 185
HOMO SAPIENS ASYMMETRY......Page 193
SUGGESTIONS FOR FURTHER READING......Page 194
REFERENCES......Page 195
LIST OF SIDEBARS AND FIGURES......Page 196
7 THE HANDEDNESS OF HOMO SAPIENS......Page 198
ARE YOU RIGHT-HANDED OR LEFT-HANDED?......Page 199
THE STATISTICS OF HANDEDNESS......Page 201
THE ORIGIN OF LEFT-HANDEDNESS......Page 206
THE HUMAN GENETICS OF HANDEDNESS......Page 209
SUMMARY......Page 215
SUGGESTIONS FOR FURTHER READING......Page 216
REFERENCES......Page 217
LIST OF SIDEBARS AND FIGURES......Page 218
8 LIVING IN A RIGHT-HANDER’S WORLD......Page 220
CLOCKWISE AND COUNTERCLOCKWISE (OR ANTICLOCKWISE) ROTATION......Page 221
HELICAL STAIRWAYS......Page 224
AROUND THE HOUSE......Page 227
MAKING MUSIC LEFT-HANDED......Page 228
THE CHIRALITY OF WRITING......Page 230
SPORTS AND THE LEFT-HANDER......Page 233
AMERICAN BASEBALL: THE CHIRAL SPORT......Page 239
DRIVING ON THE LEFT OR RIGHT SIDE......Page 244
WINDMILLS......Page 247
SUMMARY......Page 250
LIST OF SIDEBARS AND FIGURES......Page 251
9 THE ASYMMETRIC UNIVERSE......Page 254
LIST OF FIGURES......Page 257
APPENDIX......Page 258
BIOGRAPHY......Page 262
INDEX......Page 264