Chemistry

through the looking glass

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

HANDED
 DCORE
F O R HAR
CHEMISTRY see..
 LECTURE NOTES
AVAILAB L E FR O M:
http://www.mass
ey.ac.nz/~gjrowla
n/teaching.html
 E R E G O E S .
H
“”
“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

PROBABLY NOT
GOOD FOR KITTY from PetLvr.com
 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
 OH
HO
OH
O
HO OH
O OH

HO
O OH
lactose β-galactosidase
milk sugar

OUR BODIES
will only
ACCEPT ONE
why?
NOR M AL L Y

©Renaissance Pictures
MIRROR IMAGES ©Renaissance Pictures
AARREEID
ENTICAL ©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

!
DIFFERENT ©Renaissance Pictures
 THATL
2M I R R OR OOK
THE. .SAME. .
IMAGES ©Marvel/Sony/Activision
 but
are DIFFERENT

©Marvel/Sony
. ARE. .
chiral
W HA T DO E S
THIS ME A N?
 LETS LOOK
AT REAL WORLD
THE
OBJECTS
ARE 3D
EVERY
OBJECT
HAS .
 A
MIRROR
IMAGE
IF THE MIRROR IM AG E S

ARE ID E N T I C A L . .
THEY CAN. .
OCCUPY THE. .
SAME SPACE
THEY ARE

SUPE R P O S A BL E
IDENITCAL MIRROR IMAGES ARE

achiral
 QUICK
ENGLISH
LESSON
 SUPERPOSABLE
AND
SUPERIMPOSABLE
are NOT
th e S A M E
 F
.EX A M PES
L O

ach i r a l
OBJECTS. .
TENNIS
RACKET

w it h o u t w r it in g
 COFFEE
CUP

without writing
SPOON
SOCKS
BUT
 SOME MIRROR IM AG E S

ARE
© 2005 Krzysztof P. Jasiutowicz
DIFFERENT
SOME MIRROR IM AG E S

ARE
DIFFERENT
 THEY ARE

NON-SUPE R P O S A B LE
 THEY ARE

NON-SUPE R P O S A B LE
 THEY ARE

NON-SUPE R P O S A B LE
 THEY ARE

NON-SUPE R P O S A B LE
DOES NOT
MATTER
HOW YOU
TWIST
O R TU RN
 THEY
NEVER
OCCUPY
THHEE SAME
T

SPACE
 THEY
NEVER
OCCUPY
THHEE SAME
T

SPACE
 THEY ARE

NON-SUPE R P O S A B LE
 SUCH OBJECTS ARE

chiral
 F
.EX A M PL ES O

chi r a l . .
OBJECTS. .
 HA
LEFT or
RIGHT
ND E D
GOLF CLUBS
CORK SCREW
 different...

. . .F
LEFT or
RIGHT O O T E D
©M@nuDia @ Flickr
SHOES
chirality
IN
NATURE
 BIN D W E E D
anti-
CLOCKWISE ©Jeanne Roe @ flickr
 HONEYSUCKLE
©red betty black@Flickr
CLOCKWISE
 TRY
RACING 2
HONEYSUCKLE
VINES
TWISTED in
OPPOSITE
©red betty black@Flickr DIREC T I O N S
photograph: Willi Rolfes
SNAIL SHELLS
 RIGHT HANDED
SNAILS
ONLY MATE
WITH
RIGHT HANDED
SNAILS
photograph: Willi Rolfes
 MO L EC U L E S
CAN BE
a c h i r a l
 O
H H
WATER
 O CH 3
H3C N
N

N N
O
CH 3

CAFFEINE
 O L EC
M CAN BEUL E S
ch i r a l . .
AMINO ACIDS
(S)-(L)-ALANINE

O
C CH3
HO C
H NH2
ENZ Y ME S

INSULIN
hexamer
 DNA

from Rensselaer Polytechnic Institute's Biological Honors Society

 WHY
IS
IMPO R TA NT ?
THIS
AN achiral OBJECT
 AN achiral OBJECT

CAN INTE W IT H B O T H..

RACT
MIRROR IM AG E S
.EQUALLY
WELL
 ARE
PRO PE R T I E S
IDE N T I C A L
 A
SPOON
INTERACTS
WITH
LEFT or HAND
RIGHT
IDENTICALLY ©Miramax Films
BUT
A chiral OBJECT
 A chiral OBJECT

INTERACTS
DIFFERENTLY WITH EACH. .
MIRROR
I M A G E

©DrStarbuck @ Flickr
 THE LEFT SHOE
ONLY
FI T S T H E
LEFT FOOT

©DrStarbuck @ Flickr
TIGER. WOODS
USES
RIGHT-HANDED
CLUBS
AS HE IS
RIGHT - H A N D ED

©SportsbookTM
 ALTHOUGH
HE CAN P R O B A B L Y
USE BOTH!

©SportsbookTM
 M O L EC UL E S
ARE THE
SAME..
AN achiral MOLECULE
O
Et H
 AN achiral MOLECULE
O
Et H

O O
H H
HO OH
OH HO

CAN INTE W IT H B O T H..

RACT
 MIRROR IMA G E S I D E N T I C A L L Y
O
Et H
O O
H H
HO OH
OH HO

O O
H H
HO Et Et OH
O O
BUT
A chiral MOLECULE

OH
 A chiral MOLECULE

OH

INTERACTS
DIFFERENTLY WITH EACH. .
 MIRROR IMAGE
O O
H H
HO OH
OH HO

OH
 O
H O
HO H
OH H HO
O
OH

S L O W R E ACTION
 O
O H
H OH
OH H HO
O
OH

FAST REACTION
PROBLEM!
WE ARE chi r a l .
 .ENZ Y M E S &
PROTEINS
are
chiral

Marrero, Mallorquí-Fernández, Guevara, García-Castellanos, Gomis-Rüth, J. Mol. Biol., 2006, 361, 506-521
 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...
 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...
 IMAGINE EACH HAND IS A

MIRRO R IM AG E OF A DRUG..
© 2005 Krzysztof P. Jasiutowicz
THE
EN Z Y ME
I S A G L O VE . .
ONLY ONE.
HAND FI TS !
PROBLEM!
T. H. .E. OTHER HAND
MIGHT BE
UP !
TO N O G O O D

©Dreamworks / WB
 TRIVIAL
EXAMPLES
.S ME L L
CH3

H
H3C
(R)-limone
ne
oranges
©Patrick J. Lynch 2006
.S ME L L . .AND THE
MIRROR
IMAGE
CH3

H
CH 3
ne
(S)-limone
lemons
.T A ST E
CH3
O

H
CH3
(R)-carvon
e
spearmint
©Patrick J. Lynch 2006
.T A ST E . .AND THE
MIRROR
IMAGE
CH 3
O

H
H3C
e
(S)-carvon
caraway
 THE REAL

©Fir0002@wikimedia commons PRO BL EM

 O O
H H
N N

O O
O N O O N O
H H

t hal i d o mid e (S) - t h al id o m id e

(R)- causes
combats
birth defects
morning sickness

©Trois Têtes (TT)@Flickr

 . MANY E X A M PL E S

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
. MANY E X A M PL E S

Me Me
NMe2 Me2N

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

O Ph Ph O
O O
Et Et
novrad darvon
cough-suppressant painkiller
 .wh o sa i d
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
“”
“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

KITTY.
SHOULD
NOT
DRINK I T!
from PetLvr.com
 gareth
(Dr. GJ Rowlands)

thanks

www.massey.ac.nz/~gjrowlan
these slides were prepared whilst listening to
the national