Talk:Amadori rearrangement

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Proposed Merge with Amadori product[edit]

Although the focus is slightly different, the two pages have complementary information on essentially the same reaction, and they are both short, so making a too long article is not an issue. -- 13:38, 31 July 2007 (UTC)

  • yep a merge is in order, clearly identical V8rik 20:42, 31 July 2007 (UTC)
  • Done merge V8rik (talk) 17:56, 5 January 2008 (UTC)

Article wrong[edit]

This article is wrong! It is not the formation of AGEs it is describing but the formation of dicarbonyls from a reducing sugar. My reference for this statement is: Wolff, S. P. and Dean, R. T. (1987) Biochem J 245, 243-50*.

Based on the article above I suggest that the title should be "Dicarbonyl formation from the Schiff base". Furthermore, the following section is to be used in stead:

There is a common chemical reaction necessary for the formation of dicarbonyls, the so-called maillard reaction (*). The formation of dicarbonyls from a reducing sugar involves the following steps. The first step involves the formation of a Schiff base. For example the aldehyde group of a glucose molecule will combine with the amino group of a lysine molecule (in a protein) to form an imine or Schiff base (carbon-nitrogen double bond). The next step is the formation of an Amadori product. The Amadori product is a re-arrangement from the Schiff base wherein the hydrogen atom from the hydroxyl group adjacent to the carbon-nitrogen double bond moves to bond to the nitrogen, leaving a relative stable ketone (ketosamine). The last step of dicarbonyl formation from a reducing sugar is actually an intermediate reaction between the Schiff base re-arrangement and ketosamine formation. (*). The Schiff base is fragmented by a poorly understood mechanism, where the nitrogen bond is broken producing an amine (R-NH2) and a hydroxyaldehyde. In short, the hydroxyaldehyde is reduced sequentially by transition metals and O2 producing the dicarbonyls and O2-. The O2- is subsequentially converted into H2O2 by SOD. —The preceding unsigned comment was added by (talk) 22:46, August 22, 2007 (UTC)