Everything about The Lobry-de Bruyn-van Ekenstein Transformation totally explained
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.
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.
Reaction mechanism
The following scheme describes the
reaction mechanism where R is any
organic residue.
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.
Stereochemistry
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 equilibrium 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.
Further Information
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