Chemistry through the looking glass

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Layman's introduction to chirality in chemistry. Originally a lecture to sixth formers and high school students.

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  • Gareth, thank you! I've been trying to find an instructional set to help conceptualize some basic ORGO topics, like chirality, and ALL the presentations I've looked over thus far have been fantastic! They're detailed enough to be memorable without overwhelming the point and sequentially prepared in a manner better suiting a more through grasp on the topic. I commend your address of chemistry; you should be proud of yourself for reaching beyond the walls of your institution to better educate folks like myself. Again, thank you!
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  • @DanielCatron thanks for the correction. An embarrassing error considering I have just finished reading 'The Annotated Alice' by Lewis Carroll (and Martin Gardner). Will correct soon(ish).
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  • One correction to slides 8 and 117: Lewis Carroll is the author of the quote. C.S. Lewis is another fantastic author who has written within the same genre (e.g., 'The Magician's Nephew').
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  • Truly inspiring! Thank you for sharing your passion for chemistry :)
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  • Inspiring
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Chemistry through the looking glass

  1. 1. Chemistry through the looking glass Gareth J Rowlands Massey University
  2. 2. OR A LAYMAN`S GUIDE to
  3. 3. WHY MOLECULES or BE LEFT or RIGHT CAN HANDED
  4. 4. RDCORE F OR HA CHEMISTRY see..
  5. 5. LECTURE NOTES AVAILAB LE FROM: http://www.mass ey.ac.nz/~gjrowla n/teaching.html
  6. 6. HER EG OE S.
  7. 7. “” “How would you like to live in Looking-glass House, Kitty? I wonder if they'd give you milk, there? Perhaps Looking-glass milk “” isn't good to drink... C. S. Lewis “Through the Looking-Glass, and What Alice Found There” ©American McGee’s Alice - Electronic Arts
  8. 8. PROBABLY NOT GOOD FOR KITTY from PetLvr.com
  9. 9. OH OH HO OH OH HO O O HO OH OH OH O OH HO O HO OH O OH HO O lactose looking-glass milk sugar milk THESE MOLECULES ARE DIFFERENT
  10. 10. OH HO OH O HO OH O OH HO O OH lactose β-galactosidase milk sugar OUR BODIES will only ACCEPT ONE
  11. 11. why?
  12. 12. NORMALLY ©Renaissance Pictures
  13. 13. MIRROR IMAGES ©Renaissance Pictures
  14. 14. AREID RE E A NTICAL ©Renaissance Pictures
  15. 15. BUT
  16. 16. SOMETIMES ©Renaissance Pictures
  17. 17. THEY ARE ©Renaissance Pictures
  18. 18. ! DIFFERENT ©Renaissance Pictures
  19. 19. Buy “If Chins Could Kill, Confessions of a “B” Movie Actor” by Bruce Campbell ! DIFFERENT ©Renaissance Pictures
  20. 20. THATL 2M IRROR OOK THE.SAME. . . IMAGES ©Marvel/Sony/Activision
  21. 21. but are DIFFERENT ©Marvel/Sony . ARE. .
  22. 22. chiral
  23. 23. W HAT DOES THIS ME AN?
  24. 24. LETS LOOK AT REAL WORLD THE
  25. 25. OBJECTS ARE 3D
  26. 26. EVERY OBJECT HAS .
  27. 27. A MIRROR IMAGE
  28. 28. IF THE MIRROR IM AGES ARE ID ENTICAL. .
  29. 29. THEY CAN. .
  30. 30. OCCUPY THE. .
  31. 31. SAME SPACE
  32. 32. THEY ARE SUPE RPOSABLE
  33. 33. IDENITCAL MIRROR IMAGES ARE achiral
  34. 34. QUICK ENGLISH LESSON
  35. 35. SUPERPOSABLE AND SUPERIMPOSABLE are NOT th e SAME
  36. 36. ES OF .EX AMPL ach iral OBJECTS. .
  37. 37. TENNIS RACKET w ithout writing
  38. 38. COFFEE CUP without writing
  39. 39. SPOON
  40. 40. SOCKS
  41. 41. BUT
  42. 42. SOME MIRROR IM AGES ARE © 2005 Krzysztof P. Jasiutowicz DIFFERENT
  43. 43. SOME MIRROR IM AGES ARE DIFFERENT
  44. 44. THEY ARE NON-SUPE RPOSABLE
  45. 45. THEY ARE NON-SUPE RPOSABLE
  46. 46. THEY ARE NON-SUPE RPOSABLE
  47. 47. THEY ARE NON-SUPE RPOSABLE
  48. 48. DOES NOT MATTER HOW YOU TWIST O R TURN
  49. 49. THEY NEVER OCCUPY THHEE SAM T E SPACE
  50. 50. THEY NEVER OCCUPY THHEE SAM T E SPACE
  51. 51. THEY ARE NON-SUPE RPOSABLE
  52. 52. SUCH OBJECTS ARE chiral
  53. 53. ES OF .EX AMPL chi ral.. OBJECTS. .
  54. 54. HANDED LEFT or RIGHT GOLF CLUBS
  55. 55. CORK SCREW
  56. 56. different... . . .F LEFT or RIGHT OOTED ©M@nuDia @ Flickr SHOES
  57. 57. chirality IN NATURE
  58. 58. BIN DWEED anti- CLOCKWISE ©Jeanne Roe @ flickr
  59. 59. HONEYSUCKLE ©red betty black@Flickr CLOCKWISE
  60. 60. TRY RACING 2 HONEYSUCKLE VINES TWISTED in OPPOSITE ©red betty black@Flickr DIREC TIONS
  61. 61. photograph: Willi Rolfes SNAIL SHELLS
  62. 62. RIGHT HANDED SNAILS ONLY MATE WITH RIGHT HANDED SNAILS photograph: Willi Rolfes
  63. 63. MO LECULES CAN BE a chi ral
  64. 64. O H H WATER
  65. 65. O CH 3 H3C N N N N O CH 3 CAFFEINE
  66. 66. OLECULES M CAN BE ch iral..
  67. 67. AMINO ACIDS (S)-(L)-ALANINE O C CH3 HO C H NH2
  68. 68. ENZ YMES INSULIN hexamer
  69. 69. DNA from Rensselaer Polytechnic Institute's Biological Honors Society
  70. 70. WHY IS IMPORTANT? THIS
  71. 71. AN achiral OBJECT
  72. 72. AN achiral OBJECT CAN INTE WITH BOTH. . RACT
  73. 73. MIRROR IM AGES
  74. 74. .EQUALLY WELL
  75. 75. ARE PRO PERTIES IDE NTICAL
  76. 76. A SPOON INTERACTS
  77. 77. WITH LEFT or HAND RIGHT IDENTICALLY ©Miramax Films
  78. 78. BUT
  79. 79. A chiral OBJECT
  80. 80. A chiral OBJECT INTERACTS DIFFERENTLY WITH EACH. .
  81. 81. MIRROR I MAGE ©DrStarbuck @ Flickr
  82. 82. THE LEFT SHOE ONLY FI TS THE LEFT FOOT ©DrStarbuck @ Flickr
  83. 83. TIGER. WOODS USES RIGHT-HANDED CLUBS AS HE IS RIGHT -HANDED ©SportsbookTM
  84. 84. ALTHOUGH HE CAN PROBABLY USE BOTH! ©SportsbookTM
  85. 85. M OLECULES ARE THE SAME..
  86. 86. AN achiral MOLECULE O Et H
  87. 87. AN achiral MOLECULE O Et H O O H H HO OH OH HO CAN INTE WITH BOTH. . RACT
  88. 88. MIRROR IMA GES IDENTICALLY O Et H O O H H HO OH OH HO O O H H HO Et Et OH O O
  89. 89. BUT
  90. 90. A chiral MOLECULE OH
  91. 91. A chiral MOLECULE OH INTERACTS DIFFERENTLY WITH EACH. .
  92. 92. MIRROR IMAGE O O H H HO OH OH HO OH
  93. 93. O H O HO H OH H HO O OH S LOW REACTION
  94. 94. O O H H OH OH H HO O OH FAST REACTION
  95. 95. PROBLEM!
  96. 96. WE ARE chi ral.
  97. 97. .ENZ YMES & PROTEINS are chiral Marrero, Mallorquí-Fernández, Guevara, García-Castellanos, Gomis-Rüth, J. Mol. Biol., 2006, 361, 506-521
  98. 98. ONLY ONE H MIRROR R N S O IMAGE.. N O OH O penicillin O OH O O N S R N H Marrero et al., J. Mol. Biol., 2006, 361, 506-521 - apologies, this enzyme is involved in β-lactam resistance...so the following is not true...
  99. 99. FITS. . R H N S O N O OH O O OH O .(DOES US O N R N H ANY S GOOD) Marrero et al., J. Mol. Biol., 2006, 361, 506-521 - apologies, this enzyme is involved in β-lactam resistance...so the following is not true...
  100. 100. IMAGINE EACH HAND IS A MIRROR IMAGE OF © 2005 Krzysztof P. Jasiutowicz A DRUG..
  101. 101. THE EN ZY ME I S A GLOVE. .
  102. 102. ONLY ONE. HAND FITS!
  103. 103. PROBLEM!
  104. 104. TH.E. OTHER HAND .. MIGHT BE UP TO NO GOOD! ©Dreamworks / WB
  105. 105. TRIVIAL EXAMPLES
  106. 106. .S ME LL CH3 H H3C (R)-limone ne oranges ©Patrick J. Lynch 2006
  107. 107. .S ME LL . .AND THE MIRROR IMAGE CH3 H CH 3 ne (S)-limone lemons
  108. 108. .T ASTE CH3 O H CH3 (R)-carvon e spearmint ©Patrick J. Lynch 2006
  109. 109. .T ASTE . .AND THE MIRROR IMAGE CH 3 O H H3C e (S)-carvon caraway
  110. 110. THE REAL ©Fir0002@wikimedia commons PRO BLEM
  111. 111. O O H H N N O O O N O O N O H H (R)- thalidomide (S)-thalidomide combats causes birth defects morning sickness ©Trois Têtes (TT)@Flickr
  112. 112. . MANY E XAMPLES Et OH OH Et H H N N N N H H OH Et Et OH Ethambutol (R,R)-enantiomer tuberculostatic (anti-TB) causes blindness ©Brookhaven National Laboratory
  113. 113. . MANY E XAMPLES Me Me NMe2 Me2N O Ph Ph O O O Et Et novrad darvon cough-suppressant painkiller
  114. 114. .see what they did with the names? Me Me NMe2 Me2N O Ph Ph O O O Et Et novrad darvon cough-suppressant painkiller
  115. 115. .who said scientists have not got Me a sense Me of humour? NMe2 Me2N O Ph Ph O O O Et Et novrad darvon cough-suppressant painkiller
  116. 116. “” “How would you like to live in Looking-glass House, Kitty? I wonder if they'd give you milk, there? Perhaps Looking-glass milk “” isn't good to drink... C. S. Lewis “Through the Looking-Glass, and What Alice Found There” ©American McGee’s Alice - Electronic Arts
  117. 117. KITTY. SHOULD NOT DRINK IT! from PetLvr.com
  118. 118. gareth (Dr. GJ Rowlands) thanks www.massey.ac.nz/~gjrowlan these slides were prepared whilst listening to the national

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