Strecker amino acid synthesis

Schematic of the Strecker amino acid synthesis. Reagents: aldehyde, ketone, primary amine, ammonia, metal cyanide, acid catalyst, water. Product: alpha-amino acid.

The Strecker amino acid synthesis is an organic reaction used to convert an aldehyde or ketone and a pri-mary amine or ammonia to an α-amino acid using a metal cyanide, acid catalyst, and water. The mecha-nism begins with the acid catalyzed reaction of the carbonyl with the amine to give the corresponding imine. The imine is then attacked by the cyanide to provide a nitrile intermediate. The nitrile gets protonated by the acid, is attacked by a molecule of water and after a series of proton transfer steps results in an amide intermediate. In the reaction's acid conditions, the amide gets protonated and the amine group is displaced by water to eventually yield the carboxylic acid group and the final amino acid product.[1][2]


Mechanism of the Strecker amino acid synthesis.


Strecker, A. Ann. Chem. Pharm. 1850, 75, 27–45.
Strecker, A. Ann. Chem. Pharm. 1854, 91, 349–351.