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Chemistry
through the looking glass



Gareth J Rowlands
Massey University
OR
A LAYMAN`S
   GUIDE to
WHY MOLECULES
         or
 BE LEFT or RIGHT
CAN


    HANDED
RDCORE
F OR HA
CHEMISTRY see..
LECTURE NOTES
     AVAILAB LE FROM:
http://www.mass
                ey.ac.nz/~gjrowla
                                 n/t...
HER EG OE S.
“”
“How would you like to live
   in Looking-glass House,
  Kitty? I wonder if they'd
    give you milk, there?
Perhaps Lo...
PROBABLY NOT
GOOD FOR KITTY   from PetLvr.com
OH                             OH
  HO                                            OH
                     OH     HO
      ...
OH
HO
                   OH
           O
HO             OH
       O            OH

 HO
               O    OH
       lacto...
why?
NORMALLY




           ©Renaissance Pictures
MIRROR IMAGES   ©Renaissance Pictures
AREID
  RE E
A      NTICAL   ©Renaissance Pictures
BUT
SOMETIMES   ©Renaissance Pictures
THEY ARE   ©Renaissance Pictures
!
DIFFERENT   ©Renaissance Pictures
Buy “If Chins Could
            Kill, Confessions of a
             “B” Movie Actor” by
               Bruce Campbell




...
THATL
2M IRROR         OOK
           THE.SAME. .
             .
 IMAGES         ©Marvel/Sony/Activision
but
               are DIFFERENT




©Marvel/Sony
                 . ARE. .
chiral
W HAT DOES
THIS   ME AN?
LETS LOOK
AT REAL WORLD
THE
OBJECTS
  ARE     3D
EVERY
OBJECT
  HAS .
A
MIRROR
 IMAGE
IF THE MIRROR    IM AGES




                ARE ID ENTICAL. .
THEY   CAN. .
OCCUPY   THE. .
SAME   SPACE
THEY      ARE




SUPE RPOSABLE
IDENITCAL MIRROR IMAGES ARE




    achiral
QUICK
ENGLISH
LESSON
SUPERPOSABLE
          AND
SUPERIMPOSABLE
       are NOT
     th e SAME
ES OF
.EX AMPL
ach   iral
 OBJECTS. .
TENNIS
RACKET




         w ithout writing
COFFEE
                    CUP




without writing
SPOON
SOCKS
BUT
SOME MIRROR                 IM AGES




                                           ARE
© 2005 Krzysztof P. Jasiutowicz
   ...
SOME MIRROR   IM AGES




                       ARE
                DIFFERENT
THEY       ARE




NON-SUPE RPOSABLE
THEY       ARE




NON-SUPE RPOSABLE
THEY       ARE




NON-SUPE RPOSABLE
THEY       ARE




NON-SUPE RPOSABLE
DOES NOT
MATTER
HOW YOU
TWIST
O R TURN
THEY
   NEVER
    OCCUPY
THHEE SAM
T         E
 SPACE
THEY
   NEVER
    OCCUPY
THHEE SAM
T         E
 SPACE
THEY       ARE




NON-SUPE RPOSABLE
SUCH OBJECTS ARE




chiral
ES OF
.EX AMPL
  chi  ral..
 OBJECTS. .
HANDED
LEFT or
 RIGHT
GOLF CLUBS
CORK SCREW
different...




                         . . .F
                    LEFT or
                     RIGHT      OOTED
©M@nuDi...
chirality
   IN
NATURE
BIN  DWEED
anti-
CLOCKWISE     ©Jeanne Roe @ flickr
HONEYSUCKLE
©red betty black@Flickr
                          CLOCKWISE
TRY
                             RACING 2
                          HONEYSUCKLE
                               VINES
     ...
photograph: Willi Rolfes
                           SNAIL SHELLS
RIGHT HANDED
                                 SNAILS
                             ONLY MATE
                              ...
MO    LECULES
CAN BE
  a    chi  ral
O
H           H
    WATER
O      CH 3
H3C              N
      N

          N      N
  O
          CH 3


CAFFEINE
OLECULES
M CAN BE
  ch  iral..
AMINO ACIDS
(S)-(L)-ALANINE



       O
       C       CH3
  HO       C
       H NH2
ENZ YMES




INSULIN
hexamer
DNA




from Rensselaer Polytechnic Institute's Biological Honors Society
WHY
  IS
       IMPORTANT?
THIS
AN achiral OBJECT
AN achiral OBJECT




CAN INTE      WITH BOTH. .
         RACT
MIRROR   IM AGES
.EQUALLY
   WELL
ARE
PRO PERTIES
IDE NTICAL
A
 SPOON
INTERACTS
WITH
 LEFT or HAND
  RIGHT
IDENTICALLY     ©Miramax Films
BUT
A   chiral OBJECT
A    chiral OBJECT




INTERACTS
    DIFFERENTLY WITH EACH. .
MIRROR
 I MAGE


          ©DrStarbuck @ Flickr
THE LEFT SHOE
       ONLY
 FI TS THE
LEFT FOOT


                 ©DrStarbuck @ Flickr
TIGER. WOODS
        USES
RIGHT-HANDED
    CLUBS
         AS HE IS
   RIGHT -HANDED

           ©SportsbookTM
ALTHOUGH
HE CAN PROBABLY
      USE BOTH!




          ©SportsbookTM
M  OLECULES
ARE THE
        SAME..
AN achiral MOLECULE
           O
      Et       H
AN achiral MOLECULE
                        O
                   Et       H



              O                  O
        ...
MIRROR                    IMA GES IDENTICALLY
                                     O
                                Et   ...
BUT
A   chiral MOLECULE


         OH
A    chiral MOLECULE


               OH




INTERACTS
    DIFFERENTLY WITH EACH. .
MIRROR   IMAGE
         O                      O
     H                              H
HO                                 ...
O
     H                              O
HO                              H
             OH        H   HO
                  ...
O
    O                              H
        H                              OH
            OH   H        HO
O
          ...
PROBLEM!
WE ARE   chi ral.
.ENZ YMES &
                                                                                                  PROTEINS
   ...
ONLY ONE
                                                                                                                 ...
FITS. .                                                                                   R
                              ...
IMAGINE EACH HAND IS A




           MIRROR IMAGE OF
© 2005 Krzysztof P. Jasiutowicz
                                   A...
THE
EN ZY ME
I S A GLOVE. .
ONLY ONE.
HAND FITS!
PROBLEM!
TH.E. OTHER HAND
 ..
     MIGHT BE
    UP
    TO NO GOOD!



          ©Dreamworks / WB
TRIVIAL
EXAMPLES
.S ME LL
                                    CH3




                        H
                      H3C
                 ...
.S ME LL        . .AND THE
                MIRROR
                 IMAGE
    CH3




        H
       CH 3
           ne
(...
.T ASTE
                   CH3
                               O



                 H
               CH3
          (R)-car...
.T ASTE           . .AND THE
                  MIRROR
                   IMAGE
       CH 3
O



        H
        H3C
    ...
THE REAL

©Fir0002@wikimedia commons   PRO BLEM
O                     O
                           H                     H
                     N                         ...
. MANY E XAMPLES



                  Et                       OH   OH                 Et
                                ...
. MANY E XAMPLES


           Me                   Me
                 NMe2   Me2N

       O Ph                     Ph O
 ...
.see what
                        they did with
                         the names?
         Me                   Me
     ...
.who said
                          scientists
                         have not got
         Me
                         ...
“”
“How would you like to live
   in Looking-glass House,
  Kitty? I wonder if they'd
    give you milk, there?
Perhaps Lo...
KITTY.
SHOULD
     NOT
 DRINK IT!   from PetLvr.com
gareth
        (Dr. GJ Rowlands)

              thanks

          www.massey.ac.nz/~gjrowlan
these slides were prepared wh...
Chemistry through the looking glass
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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.

  • Hello dear My name is mariam nasrin, I know that this email will meet you in a good health and also surprisingly but God has his own way of bringing people together. Nice to Meet you I would appreciate if you can reply me back( mariamnasrin2@gmail.com ) So that i can explain you more about me. thank Yours mariam.
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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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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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