Acetamidomalonatea) Unusual α-Amino Acids via

2. Single Molecule Platform a) Unusual α-Amino Acids via Acetamidomalonate

The probably most widely used and first approach to unnatural amino acids proceeds via alkylation of diethyl acetamidomalonate. This process is daily routine in our laboratories and provides easy access to a large number of analogues in gram scale. Racemic mixtures of both enantiomers are being produced, which need to be separated by enzymatic methods or other separation technologies.

This route is preferred, if both stereoisomers are required in comparable quantities. The limitations of this process are: Î the alkylating reagent is not available or very costly. Î only one of the two enantiomers is required. The other enantiomer is “chiral” waste, which needs to be converted into the target compound via racemization. Î available enzymes (acylases and esterases) are not able to separate both isomers. Typical compounds which are accessible through this process are phenylalanine derivatives and amino acids with certain aliphatic residues carrying additional functional groups.