[somethingtoxic]

Hello everybody! I've been studying chem for just a little while now, and I would like to know what some answers to this question would be:

If one was to add a carboxyl group to a racetam structure to render it an amino acid, where would the most beneficial place be? Here are a few examples of the racetam family structures:

Racetam structure base: http://en.wikipedia.org/wiki/2-Pyrrolidone

Analogs:

http://en.wikipedia.org/wiki/Piracetam

http://en.wikipedia.org/wiki/Aniracetam

http://en.wikipedia.org/wiki/Oxiracetam

http://en.wikipedia.org/wiki/Nefiracetam

So much thanks in advance, this is beyond my level of understanding.

[ptryon]

Hi somethingtoxic

Why do you ask? Are you planning to synthesis an amino acid from one of these compounds? If so I am not able to help. To convert 2-pyrrolidone to an amino acid would require more than simply adding an carboxyl group somewhere in the compound:
In addition to the carboxylic acid functional group, an amino acid also contains:

(1) A generic R-group (which in nature can be one of 20 different groups- ranging from a simple hydrogen to groups with fused, aromatic ring systems)

(2) An amine group (-NH₂)

(3) A hydrogen atom

Each of these groups is joined to a central, chiral carbon atom (see link). 2-pyrrolidone is essentially an amide group contained in a 5-membered ring; in order to convert this to an aminoacid you would have to break the ring and then find a way of adding the appropriate substituents to one of the carbons. Or there might be a way to substitute 2-pyrrolidone into an amino acid... but then that would be cheating... Can any real organic chemists help here??

http://en.wikipedia.org/wiki/Amino_acid

[somethingtoxic]

Thanks!

I just ended up adding the carboxyl to position 4 to render it an amino. As far as its binding characteristics, who knows?