Amadori rearrangement

The Amadori rearrangement is an <a href="/facts/Organic_reaction/SESmeGWm">organic reaction</a> describing the <a href="/facts/Acid_catalysis/JkJ7LkT6">acid or base catalyzed</a> <a href="/facts/Isomerization/sxv23uKl">isomerization</a> or <a href="/facts/Rearrangement_reaction/B1XTteIJ">rearrangement reaction</a> of the N-<a href="/facts/Glycoside/z11RwaaB">glycoside</a> of an <a href="/facts/Aldose/hKGwqzFj">aldose</a> or the <a href="/facts/Glycosylamine/IBE26bcM">glycosylamine</a> to the corresponding 1-<a href="/facts/Amino/SN7W44fv">amino</a>-1-<a href="/facts/Deoxy/je4B9r5N">deoxy</a>-<a href="/facts/Ketose/kLknGRje">ketose</a>. The reaction is important in <a href="/facts/Carbohydrate_chemistry/UAb0Qx3C">carbohydrate chemistry</a>, specifically the glycation of hemoglobin (as measured by the <a href="/facts/HbA1c/jTNaU7Jv">HbA1c</a> test).
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. This Amadori product is an intermediate in the production of <a href="/facts/Advanced_glycation_endproduct/Xv9BaHTf">advanced glycation end-products</a> (AGE)s. The formation of an advanced glycation end-product involves the oxidation of the Amadori product.

Amadori rearrangement open-in-new

Amadori rearrangement