Amadori rearrangement

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Am·a·dor·i re·ar·range·ment

a rearrangement that occurs in cross-linking reactions seen in collagen and in protein glycosylations; for example, conversion of N-glycosides of aldoses to N-glycosides of the corresponding ketoses.
[M. Amadori]
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This non-enzymatic process initially forms reversible early glycosylation products and later irreversible advanced glycosylation end-products (AGEs) via an Amadori rearrangement. The tissue accumulation of AGEs, by crosslinking with collagen, can contribute to the associated renal and microvascular complications.[2] Good glycemic control can reduce the incidence of diabetic nephropathy.
Undergoes an Amadori rearrangement, producing a ketoamine;
The aldehyde group of the glucose first forms a Schiff base with the NH2-terminal amino group, which then rearranges to a more stable amino ketone linkage by a spontaneous (nonenzymatic) reaction known as the Amadori rearrangement. The higher the blood concentration of glucose and the longer the duration of the hyperglycemia, the more HbA1c will be formed (greater percent of glucose that becomes bound to hemoglobin).
When glucose reacts with hemoglobin (Hb), the first products are Schiff bases that slowly undergo Amadori rearrangement to produce stable ketoamines (glycohemoglobin).