To use all functions of this page, please activate cookies in your browser.
With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.
- My watch list
- My saved searches
- My saved topics
- My newsletter
Lobry-de Bruyn-van Ekenstein transformation
The Lobry-de Bruyn-van Ekenstein transformation also known as the Lobry-de Bruyn-van-Alberda-van-Ekenstein transformation is a base catalyzed Aldose-Ketose-Isomerization in carbohydrate chemistry  . A typical rearrangement reaction is that between glyceraldehyde and dihydroxyacetone in a chemical equilibrium.
Additional recommended knowledge
The reaction is relevant for the industrial production of certain ketoses and was discovered in 1885 by Cornelis Adriaan Lobry van Troostenburg de Bruyn and Willem Alberda van Ekenstein.
The position of the equilibrium or the reactant to product ratio depends on concentration, solvent,pH value and temperature. At equilibrium the aldose and ketose form a mixture which in the case of the glyceraldehyde and dihydroxyacetone is also called glycerose.
The carbon atom at which the initial deprotonation takes place is a stereocenter and based on the equilibrium all reaction steps constitute a epimerization. For example, D-Glucose (an Aldose) rearranges to D-Fructose the ketose. The stereochemical configuration is lost in this reaction in the enol form. In the equililibrium the enol can be protonated from two faces resulting in the backformation of glucose and the formation of D-mannose. The final product is a mix of D-glucose, D-fructose and D-mannose.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Lobry-de_Bruyn-van_Ekenstein_transformation". A list of authors is available in Wikipedia.|