Amadori rearrangement

The Amadori rearrangement is an organic reaction describing the acid or base catalyzed isomerization or rearrangement reaction of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose.

[1] The reaction is important in carbohydrate chemistry, specifically the glycation of hemoglobin (as measured by the HbA1c test).

[2] The rearrangement is usually preceded by formation of a α-hydroxyimine by condensation of an amine with an aldose sugar.

The rearrangement itself entails intramolecular redox reaction, converting this α-hydroxyimine to an α-ketoamine: The formation of imines is generally reversible, but subsequent to conversion to the keto-amine, the attached amine is fixed irreversibly.

One study demonstrated the possibility of Amadori rearrangement during interaction between oxidized dextran and gelatine.