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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. The reaction is important in carbohydrate chemistry.
Additional recommended knowledge
The reaction mechanism is demonstrated starting from the reaction of D-mannose in its closed (1) and open-form (2) with ammonia the 1,1-amino-alcohol 3 which is unstable and loses water to the glycosylamine (again the open imine (5) and the closed form hemiaminal (4)) which is the starting point for the actual Amadori rearrangement.
By treatment of the glycosylamine with pyridine and acetic anhydride the imine group rearranges and the intermediate enol in turn rearranges to the ketone. In this particular reaction the all alcohol and amino groups are acylated as well.
The reaction is associated with the Maillard reaction with reagents naturally occurring sugars and amino acids.
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:
The first two steps in this reaction are both reversible, but the last step is irreversible.
Categories: Rearrangement reactions | Posttranslational modification
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Amadori_rearrangement". A list of authors is available in Wikipedia.|