Friday, October 22, 2010

Chiral Drugs on the Chemistry Blog

Yesterday we started Stereochemistry in my Organic Class, and on Monday Azmanam on the Chemistry Blog had a post on  Chiral Drugs.  Take a look at the structures below:

Both are used to treat gastroesophageal reflux desease (GERD, commonly known as acid reflux).  Can you see the difference in the structures?  Click the image to see a larger version.  Prilosec is sold as a racemic mixture: a 50-50 mix of the R and S enantiomers.  Nexium contains just one enantiomer - the S isomer.  This is an example of a chiral molecule whose stereogenic center is not a carbon, but rather a sulfur.  The fourth group attached to the sulfur - the one with the lowest priority - is a lone pair of electrons.  Read Azmanam 's post for a good discussion of the two.

Chemistry Blog - Nexium’s Dirty Little Secret
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