| Version | Summary | Created by | Modification | Content Size | Created at | Operation |
|---|---|---|---|---|---|---|
| 1 | Helena Kang | -- | 152 | 2026-10-12 09:34:10 |
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.