Chem 242 @ Dickinson

More Amino Acid Material

Today we started with an example of how enantioselective synthesis can be an effective technique for manufacturing amino acids. The trick is to introduce some optically active element into the reaction in such a way that only (or mostly) one of the possible developing chiral centers is formed.

Most of the class was centered around determining the amino acids present in a peptide. The total array of amino acids can easily be determined by hydrolysis and then isolating each of the resultant amino acids. However, to determine the correct order in which they are aligned, it is necessary to do something much more interesting, such as an Edman degradation. In this process, the N-terminal amino acid is removed from the rest of the peptide and incorporated into a heterocyclic compound. This compound is unique for each amino acid and therefore it is trivial to identify the N-terminal amino acid. Even better, the rest of the peptide remains intact so that the next amino acid in line becomes the new N-terminal amino acid and so the process can be repeated all the way down the line, identifying each amino acid in order.

posted by DCChem @ 12:29 PM