Amadori rearrangement
Template:Short description 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. This Amadori product is an intermediate in the production of advanced glycation end-products (AGE)s. The formation of an advanced glycation end-product involves the oxidation of the Amadori product.
Food chemistry
The reaction is associated with the amino-carbonyl reactions (also called glycation reaction, or Maillard reaction)[3] in which the reagents are naturally occurring sugars and amino acids. One study demonstrated the possibility of Amadori rearrangement during interaction between oxidized dextran and gelatine.[4]
History
The Amadori rearrangement was discovered by the organic chemist Mario Amadori (1886–1941), who in 1925 reported this reaction while studying the Maillard reaction.[5][6]
See also
- Fructoselysine, the Amadori product derived from glucose and lysine
- Glycated hemoglobin, the Amadori product used in the HbA1c diagnostic test for diabetes
References
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- ↑ Strategic Applications of Named Reactions in Organic Synthesis (Paperback) by Laszlo Kurti, BN 0-12-429785-4
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- ↑ M. Amadori, Atti. reale accad. nazl. Lincei, [6] 2, 337 (1925); [6] 9, 68, 226 (1929); [6] 13, 72 (1931)
- ↑ Strategic Applications of Named Reactions in Organic Synthesis (Paperback) by Laszlo Kurti, BN 0-12-429785-4
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External links
- Amadori Rearrangement, PowerPoint presentation detailing the reaction mechanism
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