Chemistry & Biochemistry 98T


 


Tyger! Tyger! burning bright
In the forests of the night,
What immortal hand or eye
Dare frame thy fearful symmetry?

– William Blake


 


Cocaine, polio virus, poems, paintings, life itself! Symmetry—or the breaking of it—is intimately related to their origins, their distinctive properties, and the effects they have on people and things with which they interact. This course will examine the language used to characterize the symmetry of objects and processes, the properties associated with symmetry, antisymmetry and asymmetry, and the implications of these properties for the origins, structure, evolution, design, and appreciation of life.

Instructor:

Dean Tantillo
Molecular Science Building 5440
tantillo@chem.ucla.edu
Meetings:
MW 10-11:30am, Young Hall 2050
• In general, each Monday meeting will consist of a lecture on the key scientific concepts underlying the readings for that week. Each Wednesday meeting will consist of a group discussion focusing on the concepts and issues from lecture and the readings.

• Attendance at both is essential and required.

Readings:
Gardner, M. The New Ambidextrous Universe; W. H. Freeman and Company: New York, 1990.

Course Reader, available from UCLA Bookstore, Ackerman Union

Course Themes:
• How scientists talk about the symmetry of macroscopic and microscopic objects and molecules

• The basic principles of chemical structure and reactions, with emphasis on pharmaceuticals and biomolecules; the "chemistry of life"

• The origins and evolution of life, which is at once dependent on both symmetry and asymmetry for its existence and proliferation

• The connections between science, art and aesthetics

• The nature and value of scientific writing, from popular science to primary research

Prerequisites:
None! Knowledge of chemistry and physics is NOT expected, and may or may not be helpful.


Ansel Adams

Course Requirements

Weekly Readings:

• It is expected that the readings for each week will be completed by the Monday of the week in which they will be discussed.
Weekly Reading Evaluations (10% of total grade):
• Due Monday of each week.
one paragraph describing what was most confusing about the reading
if you let me know what is confusing, i will try to make it clearer...
Discussions (25% of total grade):
In discussion, quality is at least as important as quantity. Your discussion grade will depend not only on how often you speak, but what you say. Informed participation is essential. Any and all opinions are welcomed—if supported by arguments based on facts.

It is essential that you give the readings a second look between the Monday lecture and the Wednesday discussion, considering the concepts discussed in lecture.

Point Group Scavenger Hunt (5% of total grade):
This assignment will involve finding examples of everyday objects that belong to particular symmetry groups, and describing the symmetry elements that they possess.

• Due Monday, Week 3

Regular Division Drawing (10% of total grade):
This assignment will involve the construction of an original regular division drawing utilizing the principles of symmetry and the methods of M. C. Escher.

• Due Monday, Week 5

Criticism of the Scientific Literature (25% of total grade):
This assignment will involve the careful reading and critical evaluation of a research article from the primary scientific literature. Approximately 5 pages.

• Choose article by Wednesday, Week 6

• Rough draft due Wednesday, Week 7; returned to you by Friday, Week 7

• Final draft due Friday, Week 8

Art Criticism (25% of total grade):
This assignment will involve the analysis of a piece of artwork, with emphasis on the influence of symmetry on it's composition and subject matter and on your reaction to it.

Approximately 4-6 pages total.

• Part 1 due Monday, Week 10; returned Wednesday, Week 10

• Part 2 due Wednesday, Week 10; returned Friday, Week 10

• Final draft due Monday, Week 11


Totals:

• Reading: ~65 pages per week, on average

• Writing: 10-15 pages total

• Exams: none


 

M. C. Escher


Detailed Lecture and Reading Schedule
 

Week 1: What defines the beauty of a face?

An introduction to scientific research and the concepts of symmetry, antisymmetry, asymmetry and pseudosymmetry. The aesthetics of symmetry.

• Gardner, Chapter 1: "Mirrors"

• Ball, P. The Self-made Tapestry: Pattern Formation in Nature; Oxford University Press: New York, 1999, Chapter 1: "Patterns," pp.1-15.

• Hargittai, I. Comp. & Maths. with Apps. 1986, 12B, 1-17: "Limits of Perfection"

• Doczi, G. Comp. & Maths. with Apps. 1986, 12B, 39-62: "Seen and Unseen Symmetries: A Picture Essay"

• Swaddle, J. P; Cuthill, I. C. Proc. R. Soc. Lond. B 1995, 261, 111-116: "Asymmetry and Human Facial Attractiveness: Symmetry may not Always be Beautiful"

Week 2: What makes one object more or less symmetrical than another?
The language of symmetry: elements and point groups. Symmetry in the macroscopic world.

• Gardner, Chapter 2: "Lineland and Flatland," Chapter 3: "Solidland," Chapter 4: "Magic"

Week 3: Was M. C. Escher a closet crystallographer?
Symmetry in the plane, tiling, screw axes, repetition, crystallographic point groups, repetition.

• Schattschneider, D. M. C. Escher–Visions of Symmetry, W. H. Freeman and Company: New

York, 1990, Chapter 1: "The Route to Regular Division," pp.1-52, Chapter 3: "The Regular Division Drawings," pp.105-125.

• MacGillavry, C. H. Comp. & Maths. with Apps. 1986, 12B, 123-138: "The Symmetry of

M. C. Escher's 'Impossible' Images"

• Mamedov, Kh. S. Comp. & Maths. with Apps. 1986, 12B, 511-529: "Crystallographic Patterns"

• Schattschneider, D. Comp. & Maths. with Apps. 1986, 12B, 673-695: "In Black and White: How to Create Perfectly Colored Symmetric Patterns"

• Rhodes, G. Crystallography Made Crystal Clear; Academic Press: San Diego, 1993, Chapter 2: "An Overview of Protein Crystallography," pp.5-27.

• http://www.yorvic.york.ac.uk/~cowtan/fourier/fourier.html

Week 4: What do snowflakes have to do with quantum chemistry?
Chemical bonding and molecular structure. Language and representation in chemistry.

Symmetry at the molecular level.

• Gardner, Chapter 11: "Crystals," Chapter 12: "Molecules," Chapter 13: "Carbon"

• Ball, Chapter 5, pp.121-127.

• Hargittai, I.; Chamberland, B. Comp. & Maths. with Apps. 1986, 12B, 1021-1038: "The VSEPR Model of Molecular Geometry"

• Drago, R., ed. Physical Methods for Chemists; Saunders, 1992, Chapter 1: "Symmetry and the Point Groups," pp.1-6.

• Kroto, H. Angew. Chem. Int. Ed. Engl. 1997, 36, 1578-1593: "Symmetry, Space, Stars, and C60 (Nobel Lecture)"

Week 5: How can a drug given to ease your pain, ruin your child's life?
Definitions of chirality, asymmetry and symmetry-breaking. Implications for molecular

structure: stereoisomerism, enantiomers, diastereomers, meso compounds, racemates.

• Gardner, Chapter 10: "The Sinistral Minority," Chapter 18: "The Ozma Problem," Chapter 19:

"Mach's Shock"

• Hegstrom, R. A.; Kondepudi, D. K. Scientific American 1990, 108-115: "The Handedness of the Universe"

• Mislow, K.; Bickart, P. Israel J. Chem. 1976, 15, 1-6: "An Epistemological Note on Chirality"

• Fox, M. A.; Whitesell, J. K. Organic Chemistry, 2nd ed.; Jones and Bartlett: Boston, 1997, p.264: "Chemical Perspectives. Thalidomide: Disastrous Biological Activity of the 'Wrong' Enantiomer"

Week 6: Can asymmetry save your life?
Chemical reactions, kinetics, thermodynamics, transition states. Racemization, amplification,

asymmetric synthesis of pharmaceutical agents. Chiral catalysts and enzyme function. Drugs which interfere with enzymes.

• Streitweiser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry, 4th

ed.; MacMillan: New York, 1992, Chapter 4: "Organic Reactions," pp.55-64.

• Testa, B.; Carrupt, P.-A.; Gal, J. Chirality 1993, 5, 105-111: "The So-Called

'Interconversion' of Stereoisomeric Drugs: An Attempt at Clarification"

• Slanina, Z. Comp. & Maths. with Apps. 1986, 12B, 585-616: "An Interplay between the

Phenomenon of Chemical Isomerism and Symmetry Requirements: A Perennial Source of Stimuli for Molecular-Structure Concepts, as well as for Algebraic and Computational Chemistry"


Week 7: Without symmetry you might just fall to pieces–literally. Why?
 

Principles of biological structure: DNA, proteins and viruses. Helical organic molecules.

Supramolecular chemistry: non-covalent forces, self-assembly processes, benefits of repetition. Engineering non-natural supermolecules.

• Gardner, Chapter 14: "Living Molecules"

• Vainshtein, B. K. Comp. & Maths. with Apps. 1986, 12B, 237-269: "Symmetry of Biological Macromolecules and their Associations"

• Blundell, T. L.; Srinivasan, N. Proc. Natl. Acad. Sci. USA 1996, 93, 14243-14248: "Symmetry, Stability, and Dynamics of Multidomain and Multicomponent Protein Systems"

• Crick, F. H. C.; Watson, J. D. Nature (London) 1956, 177, 473-75: "Structure of Small Viruses"

• Caspar, D. L. D. Nature (London) 1956, 177, 475-476: "Structure of Bushy Stunt Virus"

• http://www.bocklabs.wisc.edu/virusviztop.html

Week 8: Could life have arisen in a symmetrical world?
Origins of chirality and life.

• Gardner, Chapter 15: "The Origin of Life," Chapter 16, "The Origin of Asymmetry"

• Ponnamperuma, C.; MacDermott, A. J. Chemistry in Britain 1994, 487-490: "Cosmic Asymmetry: The Meaning of Life"

• Adair, R. K. Scientific American 1988, 258, 50-56: "A Flaw in a Universal Mirror"

• Avetisov, V. A.; Goldanskii, V. I.; Kuz'min, V. V. Physics Today 1991, 33-41: "Handedness, Origin of Life and Evolution"

• Avetisov, V. A.; Goldanskii, V. I. Physics-Uspekhi 1996, 39, 819-835: "Physical Aspects of Mirror Symmetry Breaking of the Bioorganic World"

Week 9: Can symmetry help you find a mate? Why is it that your body is symmetrical, but your organs are not?
Symmetry as pressure for natural selection, fluctuating asymmetry, implications for evolution

• Gardner, Chapter 7: "Plants and Animals," Chapter 8: "Asymmetry in Animals," Chapter 9:

"The Human Body"

• Concar, D. New Scientist 1995, 146, 40-44: "Sex and the Symmetrical Body"

• Ridley, M. Science 1992, 257, 327-328: "Swallows and Scorpionflies Find Symmetry is Beautiful"

• Johnstone, R. A. Nature 1994, 372, 172-175: "Female Preference for Symmetrical Males as a By-product of Selection for Mate Recognition"

• García-Bellido, A. Proc. Natl. Acad. Sci. USA 1996, 93, 14229-14232: "Symmetries Throughout Organic Evolution"

Week 10: Is science merely art? Is art merely science?
Science as art; art as science. Examples of symmetry in art and literature. Return to the

aesthetics of symmetry and its connection to the subconscious.

• McAllister, J. W. American Scientist 1998, 86, 174-183: "Is Beauty a Sign of Truth in

Scientific Theories?"

• Osborne, H. Comp. & Maths. with Apps. 1986, 12B, 77-82: "Symmetry as an Aesthetic Factor"

• Molnar, V.; Molnar, F. Comp. & Maths. with Apps. 1986, 12B, 291-301: "Symmetry- Making and -Breaking in Visual Art"

• Scharfenberg, P. Comp. & Maths. with Apps. 1986, 12B, 883-893: "On Symmetries in the Graphic Art of Horst Barting"

• Pavlovic, B.; Trinajtic, N. Comp. & Maths. with Apps. 1986, 12B, 197-227: "On Symmetry

and Asymmetry in Literature"

• Wilson, D. Comp. & Maths. with Apps. 1986, 12B, 101-112: "Symmetry and its 'Love- Hate' Role in Music"


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