Chemistry through the looking glass

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Information about Chemistry through the looking glass
Education

Published on November 4, 2008

Author: gjr2323

Source: slideshare.net

Description

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

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/teaching.html

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 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?

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 ! DIFFERENT ©Renaissance Pictures

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 DIFFERENT

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@nuDia @ Flickr SHOES

chirality IN NATURE

BIN DWEED anti- CLOCKWISE ©Jeanne Roe @ flickr

HONEYSUCKLE ©red betty black@Flickr CLOCKWISE

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

photograph: Willi Rolfes SNAIL SHELLS

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

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 H H HO OH OH HO CAN INTE WITH BOTH. . RACT

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

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 LOW REACTION

O O H H OH OH H HO O OH FAST REACTION

PROBLEM!

WE ARE chi ral.

.ENZ YMES & 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 MIRROR IMAGE OF © 2005 Krzysztof P. Jasiutowicz A DRUG..

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 (R)-limone ne oranges ©Patrick J. Lynch 2006

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

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

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

THE REAL ©Fir0002@wikimedia commons PRO BLEM

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

. 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

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

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

.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

“” “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 IT! from PetLvr.com

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

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