Synthesis from L-Phenylalanine to Amphetamine possible?

[TotalNoob]

Sorry for the probably dumb question, I am a complete chemistry noob. Can the experts explain to me how one would replace the carboxyl group with a methyl group? Could yeast be genetically engineered to perform the synthesis? I know there are certain enzymes like N-alpha methyltransferases that might be able to achieve this, but its probably BS. Otherwise someone else would have already done this , right? I mean our body itself transforms L-Phenylalanine -> L-Tyrosin -> L-DOPA -> Dopamine, correct?

Regards

 

[G.Patton]

It is one of the unsolved problems of organic chemistry of prohibited substances. Now, we don't have an easy methods to do this.
L-Phenylalanine -> amp

 

[beetlebb]

Strecker Degradation of amino acids (AAs) to ketones is what you are looking for.

J. Org. Chem. 29, 1424 (1964)

 

[Pussy_Kurt]

Another route is oxidation to Phenylalanine to Phenylacetonitril and then, after many steps P2P ... you know

 

[serialz]

Minor Strecker degradation products of phenylalanine and phenylglycine


"Oxidative decarboxylation of amino acids. Amino acid (5 mmol) and potassium peroxodisulfate or glyoxal (5 mmol) were dissolved in 500 ml water and the mixture was heated in the LikensNickerson apparatus [19] for 1 h and the distillate extracted with 100 ml of diethyl ether. The solvent was dried over anhydrous sodium sulfate, concentrated to 500 ml using a Snyder column and a gentle stream of nitrogen, and analyzed by GC/FID and GC/MS methods. The aqueous phase was extracted with two 50-ml and two 25-ml portions of diethyl ether. The combined extracts were dried, concentrated, and analyzed as described above. An aliquot (1 ml) of the aqueous phase was evaporated in a vacuum evaporator, the residue derivatized with diazomethane solution in diethyl ether, concentrated to 1 ml, and analyzed by GC/FID and GC/ MS."

In this reaction, phenylalanine or phenylglycine react with potassium persulphate to generate Phenylacetaldehyde and benzaldehyde respectively as the majority product.


Source:
Adamiec, J., Rössner, J., Velíšek, J. et al. Minor Strecker degradation products of phenylalanine and phenylglycine. Eur Food Res Technol 212, 135–140 (2001). https://doi.org/10.1007/s002170000234

 

[Re186]

You can try to reduce phenylalanine to phenylalaninol first, and then try to use lithium aluminum hydride (AlLiH4) for further reduction, which is feasible, and there are some more complicated electrochemical methods to achieve this conversion, But the practical value is not high