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.

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

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  • Full Name Full Name Comment goes here.
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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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  • Inspiring
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  • Awesome slides Gareth!!!!
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Chemistry through the looking glass Chemistry through the looking glass Presentation Transcript

  • 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