Why Do Enantiomers Interact Differently with Chiral Compounds?

[i_love_science]

"Resolution of enantiomers can be accomplished using column chromatography. When enantiomers are passed through a traditional column, they travel at the same rate because their properties are identical. However, if a chiral adsorbent is used, the enantiomers interact with the adsorbent differently, causing them to travel through the column at different rates."

Can anyone explain why specifically do the enantiomers interact differently with chiral compounds? Thanks.

 

[mjc123]

Imagine you work in a glove factory, and you have a conveyor belt of gloves passing you. You try on every left glove on your left hand to check for fit, and ignore the right gloves (because you leave your right hand free for manipulation). The right gloves will go through much faster than the left ones. (Not an ideal factory setup I admit, but it's just for illustration!)

 

[BillTre]

The same argument could be made with a column to which are bound antibodies to some chiral compound.
The things bound by the antibodies immobillized on the column, will slow down the progress of the chiral form being bound by the antibodies through the column.
The opposite chiral form, which the antibody will not bind and not slow down, will pass through the column at a faster rate.

 

[Mayhem]

Chiral molecules will have different intermolecular interactions with the chiral solvent much like how chiral molecules interact differently with the same receptors in cells.