Amadori product

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An Amadori product is an intermediate in the production of an advanced glycation end-product (AGE) as a result of glycation.

The formation of an advanced glycation end-product involves the following steps:

  1. Formation of a Schiff base – For example the aldehyde group of a glucose molecule will combine with the amino group of a lysine molecule (in a protein) to form an imine or Schiff base, which is a double bond between the carbon atom of the glucose and the nitrogen atom of the lysine.
  2. Formation of an Amadori product – The Amadori product is a re-arrangement from the Schiff base wherein the hydrogen atom from the hydroxyl group adjacent to the carbon-nitrogen double bond moves to bond to the nitrogen, leaving a ketone.
  3. Formation of an advanced glycation end-product (AGE) – The Amadori product is oxidized, most often by transition metal catalysis.

The first two steps in this reaction are both reversible, but the last step is irreversible.