Talk:Amadori rearrangement

Proposed Merge with Amadori product
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
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 Special:Contributions/ (talk)

Amadori rearrangement depiction and relevance
Currently, we have a lovely depiction of the rearrangement. The catch is that the relevant substrates are not ammonia but alkyl amines. So I might draw that process. Further, I am pretty sure that this process is the pathway by which hemoglobin is glycated. That process is relevant to a large segment of our readership. --Smokefoot (talk) 14:32, 9 June 2018 (UTC)