Amateur Amino Acid Synthesis

[Theophrastus]

I was thinking of making some basic amino acids recently, to try some basic dry- heat, protein synthesis. I've been playing around with some basic chemicals I have on hand, but I can't really find a way, to keep the amine and the carboxyl group, from reacting with one another. Any thoughts or ideas? At this point, I'm rather clueless. As always, help is most appreciated.

[chad lawson]

I have not got a clue but I would liKe to.

Someone help me.

[Theophrastus]

Ah, I've been doing some research and I don't have the whole answer, but I may have part of it. The Mannich reaction is one that leads to a product of an amino- carbonyl compound, which I think, can then be used as a means for the genesis of amino acids, by using a hydroxyl, as the R3 group. Here's a lovely wikipedia link which explains the reaction...

 

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

 

To do so, in a simplified form, I could use ammonia, formaldehyde and acetic acid, which would result in an amino acid, similar to glycine, only with two CH2's between the amine and carboxyl group. I would then, by means of knowing the isoelectric point, extract the amino acids from possible impurities, (which I admit shall be numerous), however I'm not quite sure about several things.

 

Firstly, will the use of an carboxylic acid group, affect tautomerization? Secondly, is this method viable, and what should one consider in terms of practical application of this? Ah practicality, as wonderful as it is, it is an annoying consideration at times...

[Lodami]

I do not really understand the process, but i'll just put my 1's and 2's. Increasing the pH to a value just past the pKa of the carboxylic group would lead to deprotonation of this group. This may help, since the resonance resulting from delocalization of electrons between the carboxylate oxygens can stabilize the carboxylate, reducing the possibility of tautomerization leading to enol formation. So as long as you control your pH U SHOULD BE FINE!!