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

  • Formaat: PDF+DRM
  • Ilmumisaeg: 22-Apr-2011
  • Kirjastus: John Wiley & Sons Inc
  • Keel: eng
  • ISBN-13: 9780470588871
  • Formaat - PDF+DRM
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  • Formaat: PDF+DRM
  • Ilmumisaeg: 22-Apr-2011
  • Kirjastus: John Wiley & Sons Inc
  • Keel: eng
  • ISBN-13: 9780470588871

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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 asymmetrychiralityhas 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.

Arvustused

"Riehl should be commended for presenting an understable introduction to chirality to such a wide audience." (Choice, October 2010).

Preface xi
List of Figures and Biographic Photographs
xv
1 The Mirror Image
1(26)
Handedness
2(3)
The Symmetry of Nonsuperimposable Mirror Images
5(6)
Nomenclature for Chiral Molecules
11(8)
Nomenclature for Dissymmetric and Other Chiral Molecules
19(5)
Summary
24(1)
Suggestions for Further Reading
24(1)
References
25(1)
List of Biographic Photographs, Sidebars, and Figures
25(2)
2 Molecular Chirality in Living Systems
27(32)
Optical Rotation
30(6)
From Biot to Pasteur
36(8)
Biochemical Homochirality
44(8)
Determination of Absolute Structures of Chiral Molecules
52(2)
Summary
54(1)
Suggestions for Further Reading
55(1)
References
55(1)
List of Biographic Photographs, Sidebars, and Figures
56(3)
3 The Origin of Chirality in Living Systems
59(22)
Must Life be Chiral?
60(2)
Mirror-Image Life?
62(1)
The Origin of Homochirality in Living Systems
63(2)
Extraterrestrial Chirality
65(5)
Nuclear Chirality
70(2)
Other Extraterrestrial Sources
72(1)
The Beginning of Life on Earth: Biochemistry
73(3)
Getting Started in the Right (or Left) Direction
76(2)
Summary
78(1)
Suggestions for Further Reading
78(1)
References
79(1)
List of Sidebars and Figures
80(1)
4 Chiral Chemistry, Recognition, and Control in Living Systems
81(30)
Chiral Chemical Evolution
81(2)
Chiral Recognition at the Molecular Level
83(4)
Examples of Chiral Recognition and Discrimination
87(17)
Smell
87(4)
Taste
91(2)
Communication
93(11)
Chirality as a Control Mechanism in Biochemistry
104(4)
Summary
108(1)
Suggestions for Further Reading
108(1)
References
108(2)
List of Biographic Photographs, Sidebars, and Figures
110(1)
5 Chirality and Drugs
111(36)
Chirality in Natural Remedies and Folk Medicines
112(2)
Enantiomeric Differences in Natural Products
114(4)
Thalidomide and Regulation of Chiral Drugs
118(3)
Chirality and Drug Activity
121(8)
Ibuprofen
121(1)
Prozac
122(1)
Cialis
123(2)
Nexium
125(3)
Lipitor
128(1)
Chiral Switching
129(2)
Ephedrine, Pseudoephedrine, and Methamphetamine
131(4)
Preparation of Pure Enantiomers
135(8)
Summary
143(1)
Suggestions for Further Reading
143(1)
References
143(2)
List of Biographic Photographs, Sidebars, and Figures
145(2)
6 The Chirality of Living Systems
147(28)
Preliminary Cautions
148(5)
Chirality in Nature
153(6)
Classification of Plant and Animal Chirality (Asymmetry)
159(11)
Symmetric Life
160(1)
Racemic Life
160(2)
Asymmetric Life
162(8)
Homo Sapiens Asymmetry
170(1)
Summary
171(1)
Suggestions for Further Reading
171(1)
References
172(1)
List of Sidebars and Figures
173(2)
7 The Handedness of Homo Sapiens
175(22)
Are you Right-Handed or Left-Handed?
176(2)
The Statistics of Handedness
178(5)
The Origin of Left-Handedness
183(3)
The Human Genetics of Handedness
186(6)
Summary
192(1)
Suggestions for Further Reading
193(1)
References
194(1)
List of Sidebars and Figures
195(2)
8 Living in a Right-Hander's World
197(34)
Clockwise and Counterclockwise (or Anticlockwise) Rotation
198(3)
Helical Stairways
201(3)
Around the House
204(1)
Making Music Left-Handed
205(2)
The Chirality of Writing
207(3)
Sports and the Left-Hander
210(6)
American Baseball: The Chiral Sport
216(5)
Driving on the Left or Right Side
221(3)
Windmills
224(3)
Summary
227(1)
Suggestions for Further Reading
228(1)
References
228(1)
List of Sidebars and Figures
228(3)
9 The Asymmetric Universe
231(4)
List of Figures
234(1)
Appendix 235(4)
Biography 239(2)
Index 241
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.