Chirality in Amino Acids

What causes chirality "handedness"?

If an atom such as carbon, silicon, nitrogen, phosphorus or sulphur forms a tetrahedral structure with four different groups attached then two non-superimposable mirror images will be formed. The most common and simplest example of this is with carbon. The diagram below shows that there is no way that you can put the two molecules on top of one another and have all the groups lined up. One molecule is the mirror image of the other one.

This is an example of a molecule with a chiral centre.

 

Stereoisomer 1
Stereoisomer 2

Compare the two amino acids below (glycine and alanine). Which one shows chirality?

L-glycine
D-glycine

 

L-alanine

D_alanine

Go to Amino Acid Sidechains