Lobry de Bruyn–Van Ekenstein transformation
In
. [1] [2]The reactions are usually base catalyzed, but can also take place under acid or neutral conditions.[1] A typical rearrangement reaction is that between the aldose glyceraldehyde and the ketose dihydroxyacetone in a chemical equilibrium.
The Lobry de Bruyn–Van Ekenstein transformation 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.[3][4][5][6][7][8]
Aldose-ketose transformation
The following scheme describes the interconversion between an aldose and a ketose, where R is any organic residue.
The equilibrium or the reactant to product ratio depends on concentration, solvent, pH and temperature. At equilibrium the aldose and ketose form a mixture which in the case of the glyceraldehyde and dihydroxyacetone is also called glycerose.
A related reaction is the
Epimerization
The carbon atom at which the initial
References
- ^ a b Momcilo Miljkovic Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic Effects 2009 (Google books)
- ^ ANGYAL, S.J.: The Lobry de Bruyn–Alberda van Ekenstein transformation and related reactions, in: Glycoscience: epimerisation, isomerisation and rearrangement reactions of carbohydrates, Vol. 215, (Ed.: STÜTZ, A.E.), Springer-Verlag, Berlin, 2001, 1–14
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