Amadori rearrangement

The Amadori rearrangement converts an aldose-derived glycosylamine into a more stable 1-amino-1-deoxy-2-ketose. It is an early step in nonenzymatic reactions between reducing sugars and amino compounds.

Schiff base: A compound containing a carbon–nitrogen double bond, commonly formed when a primary amine reacts with a carbonyl compound. The glycosylamine can open to an imine-like form that undergoes the rearrangement.
Reducing sugar: A sugar that can access a form with a free carbonyl group and reduce certain chemical reagents. Its open-chain carbonyl form supplies the reactive aldose or ketose.
Glycation: The nonenzymatic attachment of sugars or sugar-derived compounds to proteins, lipids, or nucleic acids. Amadori products form during early glycation of biomolecules.
Mario Amadori: An Italian chemist who described the rearrangement of sugar–amine condensation products. The named rearrangement commemorates his work on these compounds.
Glycosylamine: A compound in which an amino group is attached to the anomeric carbon of a sugar. This is the initial sugar–amine product that rearranges.
Aldose: A monosaccharide whose open-chain form contains an aldehyde group. Aldoses form the glycosylamines that undergo the Amadori rearrangement.
HbA1c: Hemoglobin bearing a stable glucose-derived adduct at its N-terminal valine. Its formation proceeds through an early glucose–protein adduct and Amadori rearrangement.
Maillard reaction history: The scientific development of knowledge about reactions between sugars and amino compounds. Amadori’s work clarified an early chemical stage of the browning reaction Maillard first reported.
Enolization: The conversion of a carbonyl compound into an enol or an enolate through proton transfer. Proton shifts and enol-like intermediates enable conversion of the aldose-derived imine into a ketose.
Ketose: A monosaccharide whose open-chain form contains a ketone group. Ketoses typically undergo the related Heyns rearrangement instead.

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