Akabori amino acid reactions

What are Akabori amino acid reactions?

Akabori first reported this reaction in 1931. It involves synthesizing an aldehyde, an α-amino aldehyde, or a primary amine from an α-amino acid under various reaction conditions.

The Akabori amino acid reactions refer to a set of chemical processes that involve the formation of aldehydes through the oxidative decomposition of α-amino acids when they are heated with sugars.

Akabori amino-acid reaction using sugars and oxygen O2 reducing sugars
Akabori amino acid reactions using reducing sugars

The Akabori amino acid reactions involve either oxidizing amino acids using O2 in the presence of sugar or reducing amino acids using Na/Hg and HCl/EtOH to produce α-amino aldehydes.

Akabori amino-acid reactions - Na/Hg HCl/EtOH - sodium amalgam and ethanolic HCl
Akabori amino acid reactions using sodium amalgam and ethanolic HCl

To provide a comparison, the reduction of α-amino acid ester using sodium amalgam in an alcoholic solution with hydrochloric acid present results in the formation of an α-amino aldehyde.

Furthermore, under pyrolytic conditions, an α-amino acid can be converted to a primary amine in the presence of benzaldehyde.

Akabori amino-acid reactions - Conversion of α-amino acid into 1º amine in presence of benzaldehyde
Conversion of α-amino acid into 1º amine in presence of benzaldehyde

References

Shares