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

1. Chemistry
through the looking glass
Gareth J Rowlands
Massey University

3. OR
A LAYMAN`S
GUIDE to

4. WHY MOLECULES
or
BE LEFT or RIGHT
CAN
HANDED

5. RDCORE
F OR HA
CHEMISTRY see..

6. LECTURE NOTES
AVAILAB LE FROM:
http://www.mass
ey.ac.nz/~gjrowla
n/teaching.html

7. HER EG OE S.

8. “”
“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

9. PROBABLY NOT
GOOD FOR KITTY from PetLvr.com

10. 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

11. OH
HO
OH
O
HO OH
O OH
HO
O OH
lactose β-galactosidase
milk sugar
OUR BODIES
will only
ACCEPT ONE

12. why?

13. NORMALLY
©Renaissance Pictures

14. MIRROR IMAGES ©Renaissance Pictures

15. AREID
RE E
A NTICAL ©Renaissance Pictures

16. BUT

17. SOMETIMES ©Renaissance Pictures

18. THEY ARE ©Renaissance Pictures

19. !
DIFFERENT ©Renaissance Pictures

20. Buy “If Chins Could
Kill, Confessions of a
“B” Movie Actor” by
Bruce Campbell
!
DIFFERENT ©Renaissance Pictures

21. THATL
2M IRROR OOK
THE.SAME. .
.
IMAGES ©Marvel/Sony/Activision

22. but
are DIFFERENT
©Marvel/Sony
. ARE. .

23. chiral

24. W HAT DOES
THIS ME AN?

25. LETS LOOK
AT REAL WORLD
THE

26. OBJECTS
ARE 3D

27. EVERY
OBJECT
HAS .

28. A
MIRROR
IMAGE

29. IF THE MIRROR IM AGES
ARE ID ENTICAL. .

30. THEY CAN. .

31. OCCUPY THE. .

32. SAME SPACE

33. THEY ARE
SUPE RPOSABLE

34. IDENITCAL MIRROR IMAGES ARE
achiral

35. QUICK
ENGLISH
LESSON

36. SUPERPOSABLE
AND
SUPERIMPOSABLE
are NOT
th e SAME

37. ES OF
.EX AMPL
ach iral
OBJECTS. .

38. TENNIS
RACKET
w ithout writing

39. COFFEE
CUP
without writing

40. SPOON

41. SOCKS

42. BUT

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

44. SOME MIRROR IM AGES
ARE
DIFFERENT

45. THEY ARE
NON-SUPE RPOSABLE

46. THEY ARE
NON-SUPE RPOSABLE

47. THEY ARE
NON-SUPE RPOSABLE

48. THEY ARE
NON-SUPE RPOSABLE

49. DOES NOT
MATTER
HOW YOU
TWIST
O R TURN

50. THEY
NEVER
OCCUPY
THHEE SAM
T E
SPACE

51. THEY
NEVER
OCCUPY
THHEE SAM
T E
SPACE

52. THEY ARE
NON-SUPE RPOSABLE

53. SUCH OBJECTS ARE
chiral

54. ES OF
.EX AMPL
chi ral..
OBJECTS. .

55. HANDED
LEFT or
RIGHT
GOLF CLUBS

56. CORK SCREW

57. different...
. . .F
LEFT or
RIGHT OOTED
©M@nuDia @ Flickr
SHOES

58. chirality
IN
NATURE

59. BIN DWEED
anti-
CLOCKWISE ©Jeanne Roe @ flickr

60. HONEYSUCKLE
©red betty black@Flickr
CLOCKWISE

61. TRY
RACING 2
HONEYSUCKLE
VINES
TWISTED in
OPPOSITE
©red betty black@Flickr DIREC TIONS

62. photograph: Willi Rolfes
SNAIL SHELLS

63. RIGHT HANDED
SNAILS
ONLY MATE
WITH
RIGHT HANDED
SNAILS
photograph: Willi Rolfes

64. MO LECULES
CAN BE
a chi ral

65. O
H H
WATER

66. O CH 3
H3C N
N
N N
O
CH 3
CAFFEINE

67. OLECULES
M CAN BE
ch iral..

68. AMINO ACIDS
(S)-(L)-ALANINE
O
C CH3
HO C
H NH2

69. ENZ YMES
INSULIN
hexamer

70. DNA
from Rensselaer Polytechnic Institute's Biological Honors Society

71. WHY
IS
IMPORTANT?
THIS

72. AN achiral OBJECT

73. AN achiral OBJECT
CAN INTE WITH BOTH. .
RACT

74. MIRROR IM AGES

75. .EQUALLY
WELL

76. ARE
PRO PERTIES
IDE NTICAL

77. A
SPOON
INTERACTS

78. WITH
LEFT or HAND
RIGHT
IDENTICALLY ©Miramax Films

79. BUT

80. A chiral OBJECT

81. A chiral OBJECT
INTERACTS
DIFFERENTLY WITH EACH. .

82. MIRROR
I MAGE
©DrStarbuck @ Flickr

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

84. TIGER. WOODS
USES
RIGHT-HANDED
CLUBS
AS HE IS
RIGHT -HANDED
©SportsbookTM

85. ALTHOUGH
HE CAN PROBABLY
USE BOTH!
©SportsbookTM

86. M OLECULES
ARE THE
SAME..

87. AN achiral MOLECULE
O
Et H

88. AN achiral MOLECULE
O
Et H
O O
H H
HO OH
OH HO
CAN INTE WITH BOTH. .
RACT

89. 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

90. BUT

91. A chiral MOLECULE
OH

92. A chiral MOLECULE
OH
INTERACTS
DIFFERENTLY WITH EACH. .

93. MIRROR IMAGE
O O
H H
HO OH
OH HO
OH

94. O
H O
HO H
OH H HO
O
OH
S LOW REACTION

95. O
O H
H OH
OH H HO
O
OH
FAST REACTION

96. PROBLEM!

97. WE ARE chi ral.

98. .ENZ YMES &
PROTEINS
are
chiral
Marrero, Mallorquí-Fernández, Guevara, García-Castellanos, Gomis-Rüth, J. Mol. Biol., 2006, 361, 506-521

99. 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...

100. 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...

101. IMAGINE EACH HAND IS A
MIRROR IMAGE OF
© 2005 Krzysztof P. Jasiutowicz
A DRUG..

102. THE
EN ZY ME
I S A GLOVE. .

103. ONLY ONE.
HAND FITS!

104. PROBLEM!

105. TH.E. OTHER HAND
..
MIGHT BE
UP
TO NO GOOD!
©Dreamworks / WB

106. TRIVIAL
EXAMPLES

107. .S ME LL
CH3
H
H3C
(R)-limone
ne
oranges
©Patrick J. Lynch 2006

108. .S ME LL . .AND THE
MIRROR
IMAGE
CH3
H
CH 3
ne
(S)-limone
lemons

109. .T ASTE
CH3
O
H
CH3
(R)-carvon
e
spearmint
©Patrick J. Lynch 2006

110. .T ASTE . .AND THE
MIRROR
IMAGE
CH 3
O
H
H3C
e
(S)-carvon
caraway

111. THE REAL
©Fir0002@wikimedia commons PRO BLEM

112. 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

113. . 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

114. . MANY E XAMPLES
Me Me
NMe2 Me2N
O Ph Ph O
O O
Et Et
novrad darvon
cough-suppressant painkiller

115. .see what
they did with
the names?
Me Me
NMe2 Me2N
O Ph Ph O
O O
Et Et
novrad darvon
cough-suppressant painkiller

116. .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

117. “”
“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

118. KITTY.
SHOULD
NOT
DRINK IT! from PetLvr.com

119. gareth
(Dr. GJ Rowlands)
thanks
www.massey.ac.nz/~gjrowlan
these slides were prepared whilst listening to
the national