C6H12O6

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1
C6H12O6

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2
Thalidomide
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Thalidomide Story
1954 synthesized West Germany
1957 approved as sedative/soporific
1960 application to FDA denied
1961 peripheral neuritis noted ? birth
defects noted
1962 drug withdrawn in Europe Kelsey
awarded medal
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chiral carbon a carbon with four different
groups attached to it.
optical isomers molecules that differ only by
their spatial orientation.
eanantiomer relationship between 2 optical
isomers that are mirror images of each other.
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5
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6
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Glyceraldehyde Enantiomers
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Distinguishing Properties of Enantiomers (optical
isomers that are mirror images of each other)
1. They cant be superimposed
2. They rotate plane polarized light in
different directions
3. They react differently in a chiral
environment!
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11
Protein Surface binding points
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12
Protein Surface Ligands
D
L
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Protein Surface correct ligand
D
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Protein Surface incorrect ligand
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L
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Proteins are chiral molecules Eanantiomers can
react quite differently in living systems.
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GLUCOSE
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CHO H - C - OH
HO - C - H H - C - OH
H - C - OH CH2 - OH
All naturally occuring sugars are D
enantiomers
open - aldehyde
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Amino Acidnature makes only L
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L-Alanine nature only makes L amino
acids
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Thalidomide
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L teratogen
r-thalidomide
s-thalidomide
sedative soporific D