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Kang, H. Amadori Rearrangement. Encyclopedia. Available online: https://encyclopedia.pub/entry/60883 (accessed on 23 October 2026).
Kang H. Amadori Rearrangement. Encyclopedia. Available at: https://encyclopedia.pub/entry/60883. Accessed October 23, 2026.
Kang, Helena. "Amadori Rearrangement" Encyclopedia, https://encyclopedia.pub/entry/60883 (accessed October 23, 2026).
Kang, H. (2026, October 12). Amadori Rearrangement. In Encyclopedia. https://encyclopedia.pub/entry/60883
Kang, Helena. "Amadori Rearrangement." Encyclopedia. Web. 12 October, 2026.

Amadori Rearrangement

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The Amadori rearrangement is the acid- or base-mediated conversion of an N-substituted glycosylamine derived from an aldose into the corresponding 1-amino-1-deoxy-2-ketose. Initial condensation of the aldose carbonyl group with a primary amine gives an imine that cyclizes and equilibrates with glycosylamine forms. Ring opening, proton transfer through an enaminol intermediate, and reorganization of the carbonyl system shift the carbonyl functionality from C1 to C2 while retaining the nitrogen substituent at C1 [1]. The resulting ketoamine is called an Amadori product. This transformation is distinguished from the Heyns rearrangement, in which a ketose-derived glycosylamine gives a 2-amino-2-deoxyaldose, and from later dehydration, fragmentation, or oxidation reactions of the ketoamine [2]. The conceptual endpoint is the rearranged aminodeoxyketose itself; subsequent formation of heterocycles, cross-links, or advanced glycation products lies outside the definition of the rearrangement.

Amadori rearrangement glycosylamine ketoamine aminodeoxyketose
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References

  1. J. E. Hodge; Dehydrated Foods, Chemistry of Browning Reactions in Model Systems. J. Agric. Food Chem. 1953, 1, 928-943. [CrossRef]
  2. F. Micheel; Mechanism of Osazone Formation and of the Amadori Rearrangement. Angew. Chem. Int. Ed. Engl. 1964, 3, 320-320. [CrossRef]
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Subjects: Chemistry, Organic
Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register : Helena Kang
View Times: 5
Entry Collection: Organic Chemistry
Revision: 1 time (View History)
Update Date: 19 Oct 2026
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