Akabori amino-acid reaction

There are several Akabori amino acid reactions, which are named after Shirō Akabori (1900–1992), a Japanese chemist.

In the first reaction, an α-amino acid is oxidised and undergoes decarboxylation to give an aldehyde at the former α position by heating with oxygen in the presence of a reducing sugar. This reaction is useful for preparing dichlorophthalimido derivatives of peptides for mass spectral analysis.


 * [[Image:Reacción de Akabori 1.png]]

In the second reaction, an α-amino acid, or an ester of it, is reduced by sodium amalgam and ethanolic HCl to give an α-amino aldehyde. This process is conceptually similar to the Bouveault–Blanc reduction  except that it stops at the aldehyde stage rather than reducing the ester all the way to two alcohols.


 * [[Image:Reacción de Akabori 2.png]]