Chemistrythrough the looking glass

Gareth J RowlandsMassey University

ORA LAYMAN`S

GUIDE to

WHY MOLECULES

HANDEDLEFT or RIGHT

CANBE

or

FOR HARDCORE

CHEMISTRY see...

http://www.massey.ac.nz/~gjrowlan/teaching.html

LECTURE NOTES

AVAILABLE FROM:

HERE GOES...

C. S. Lewis“Through the Looking-Glass, and

What Alice Found There”“”

“”“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...

©American McGee’s Alice - Electronic Arts

from PetLvr.com

PROBABLY NOT GOOD FOR KITTY

O

OHOH

O

O

HO

HO

OHOH

HO

OH

looking-glassmilk

O

OHHO

O

O

OH

OH

HO OH

OH

HO

lactosemilk sugar

THESE MOLECULESARE DIFFERENT

O

OHHO

O

O

OH

OH

HO OH

OH

HO

lactosemilk sugar

BODIES

ACCEPT ONEwill only

OUR

β-galactosidase

why?

©Renaissance Pictures

NORMALLY

©Renaissance Pictures

MIRROR IMAGES

©Renaissance Pictures

AREIDENTICALARE

BUT

©Renaissance Pictures

SOMETIMES

©Renaissance Pictures

THEY ARE

©Renaissance Pictures

DIFFERENT!

©Renaissance Pictures

DIFFERENT!

Buy “If Chins Could Kill, Confessions of a “B” Movie Actor” by

Bruce Campbell

©Marvel/Sony/Activision

2 MIRRORIMAGES

LOOK...SAME...

THAT

THE

©Marvel/Sony

DIFFERENTbutare

..ARE...

chiral

WHAT DOES

MEAN?THIS

REAL WORLDATTHE

LETS LOOK

OBJECTSARE 3D

EVERYOBJECT

HAS...

AMIRRORIMAGE

IF THE MIRROR IMAGES

IDENTICAL...ARE

THEY CAN...

OCCUPY THE...

SAME SPACE

THEY ARE

SUPERPOSABLE

achiral

IDENITCAL MIRROR IMAGES ARE

QUICKENGLISHLESSON

SUPERPOSABLEAND

the SAME

SUPERIMPOSABLEare NOT

.EXAMPLESOF

achiralOBJECTS...

TENNISRACKET

without writing

COFFEECUP

without writing

SPOON

SOCKS

BUT

SOME MIRROR IMAGES

DIFFERENTARE

© 2005 Krzysztof P. Jasiutowicz

SOME MIRROR IMAGES

DIFFERENTARE

THEY ARE

NON-SUPERPOSABLE

THEY ARE

NON-SUPERPOSABLE

THEY ARE

NON-SUPERPOSABLE

THEY ARE

NON-SUPERPOSABLE

DOES NOTMATTER

OR TURN

HOW YOU TWIST

THEYNEVER

SPACE

OCCUPY THE SAMETHE

THEYNEVER

SPACE

OCCUPY THE SAMETHE

THEY ARE

NON-SUPERPOSABLE

chiral

SUCH OBJECTS ARE

.EXAMPLESOF

chiral..OBJECTS...

HANDED

GOLF CLUBS

LEFT orRIGHT

CORK SCREW

different...

©M@nuDia @ Flickr

.....FOOTEDLEFT orRIGHT

SHOES

chirality

NATUREIN

©Jeanne Roe @ flickr

BINDWEED

CLOCKWISEanti-

©red betty black@Flickr

HONEYSUCKLECLOCKWISE

©red betty black@Flickr

TRYRACING 2

HONEYSUCKLEVINES

TWISTED inOPPOSITE

DIRECTIONS

photograph: Willi Rolfes SNAIL SHELLS

photograph: Willi Rolfes

RIGHT HANDEDSNAILS

ONLY MATEWITH

RIGHT HANDEDSNAILS

MOLECULESCAN BE

achiral

HO

HWATER

N

N N

N

O

CH3O

H3CCH3

CAFFEINE

MOLECULESCAN BE

chiral..

CC

CH3

H NH2HO

O

AMINO ACIDS(S)-(L)-ALANINE

ENZYMES

hexamerINSULIN

from Rensselaer Polytechnic Institute's Biological Honors Society

DNA

IMPORTANT?ISTHIS

WHY

AN achiral OBJECT

WITHINTERACT

AN achiral OBJECT

CAN BOTH...

MIRROR IMAGES

.EQUALLYWELL

PROPERTIESIDENTICAL

ARE

ASPOONINTERACTS

©Miramax Films

WITHHAND

IDENTICALLY

LEFT orRIGHT

BUT

A chiral OBJECT

A chiral OBJECT

INTERACTSDIFFERENTLY WITH EACH...

©DrStarbuck @ Flickr

MIRRORIMAGE

©DrStarbuck @ Flickr

THE LEFT SHOE

FITS THE

LEFT FOOT

ONLY

©SportsbookTM

RIGHT-HANDEDAS HE IS

WOODS

CLUBS

USES

TIGER.

RIGHT-HANDED

©SportsbookTM

USE BOTH!HE CAN PROBABLY

ALTHOUGH

MOLECULESARE THE

SAME..

AN achiral MOLECULE

EtO

H

AN achiral MOLECULE

WITHINTERACTCAN BOTH...

EtO

H

OHHO

OHO

OH

OHH

MIRROR IMAGES IDENTICALLY

OHO

OHO

O

OHH

Et Et

EtO

H

OHHO

OHO

OH

OHH

BUT

A chiral MOLECULE

OH

A chiral MOLECULE

OH

INTERACTSDIFFERENTLY WITH EACH...

MIRROR IMAGE

OH

OHHO

OHO

OH

OHH

HOOH

OH

OH

H HOO

OH

SLOW REACTION

OHHO

OH

OH

HOHO

HO

FAST REACTION

PROBLEM!

chiral..AREWE

Marrero, Mallorquí-Fernández, Guevara, García-Castellanos, Gomis-Rüth, J. Mol. Biol., 2006, 361, 506-521

.ENZYMES &PROTEINS

arechiral

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...

N

S

O

OOH

HNR

O

penicillin

N

S

O

OOH

NH

R

O

MIRRORIMAGE...

ONLY ONE

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...

N

S

O

OOH

NH

R

O

N

S

O

OOH

HNR

O

FITS...

ANYGOOD)

.(DOES US

IS AIMAGINE EACH HAND

MIRROR IMAGE OF © 2005 Krzysztof P. Jasiutowicz

A DRUG...

ENZYMETHE

IS A GLOVE...

ONLY ONE..

HAND FITS!

PROBLEM!

©Dreamworks / WB

........OTHER HANDMIGHT BE

THE

NO GOOD!UPTO

EXAMPLESTRIVIAL

.SMELL

CH3

HH3C

(R)-limoneneoranges©Patrick J. Lynch 2006

.SMELL

CH3

(S)-limonenelemons

HCH3

MIRRORIMAGE

...AND THE

©Patrick J. Lynch 2006

.TASTE

(R)-carvonespearmint

CH3

HCH3

O

MIRRORIMAGE

...AND THE

.TASTE

(S)-carvonecaraway

CH3

HH3C

O

©Fir0002@wikimedia commons PROBLEMTHE REAL

©Trois Têtes (TT)@Flickr

morning sickness

(R)-thalidomidecombats

NH

H

OO

N

O

ONH

H

O O

N

O

O

birth defects

(S)-thalidomidecauses

NH

HN

OH

Et

Et

OH

Ethambutoltuberculostatic (anti-TB)

NH

HN

OH

Et

Et

OH

(R,R)-enantiomercauses blindness

©Brookhaven National Laboratory

..MANY EXAMPLES

NMe2

Me

PhO

EtO

novradcough-suppressant

Me2NMe

Ph O

EtO

darvonpainkiller

..MANY EXAMPLES

NMe2

Me

PhO

EtO

novradcough-suppressant

Me2NMe

Ph O

EtO

darvonpainkiller

.see whatthey did with the names?

NMe2

Me

PhO

EtO

novradcough-suppressant

Me2NMe

Ph O

EtO

darvonpainkiller

.who saidscientists

have not gota sense

of humour?

C. S. Lewis“Through the Looking-Glass, and

What Alice Found There”“”

“”“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...

©American McGee’s Alice - Electronic Arts

from PetLvr.com

KITTY.SHOULD

DRINK IT!NOT

gareth(Dr. GJ Rowlands)

these slides were prepared whilst listening to

thanks

www.massey.ac.nz/~gjrowlan

the national