Amadori rearrangement

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
  1. Strategic Applications of Named Reactions in Organic Synthesis (Paperback) by Laszlo Kurti, BN 0-12-429785-4
  2. Koenig, R. J.; Cerami, A. (1980). "Hemoglobin A Ic and diabetes mellitus". Annual Review of Medicine. 31: 29–34. doi:10.1146/annurev.me.31.020180.000333. PMID 6994614.
  3. This vo Kientza, Hervé. "IMARS Highligh". www.imarsonline.com/.
  4. Berillo, Dmitriy; Natalia Volkova (2014). "Preparation and physicochemical characteristics of cryogel based on gelatin and oxidised dextran". Journal of Materials Science. 49 (14): 4855–4868. Bibcode:2014JMatS..49.4855B. doi:10.1007/s10853-014-8186-3. S2CID 96843083.
  5. M. Amadori, Atti. reale accad. nazl. Lincei, [6] 2, 337 (1925); [6] 9, 68, 226 (1929); [6] 13, 72 (1931)
  6. Strategic Applications of Named Reactions in Organic Synthesis (Paperback) by Laszlo Kurti, BN 0-12-429785-4
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