Improved straightforward chemical synthesis of dihydroxyacetone phosphate through enzymatic desymmetrization of 2,2-dimethoxypropane-1,3-diol.
Dihydroxyacetone phosphate (DHAP) was synthesized in high purity and yield in four steps starting from dihydroxyacetone dimer (DHA) (47% overall yield). DHA was converted into 2,2-dimethoxypropane-1,3-diol, which was desymmetrized by acetylation with lipase AK. The alcohol function was phosphorylated to give dibenzyl phosphate ester 4. From 4, two routes were investigated for large-scale synthesis of DHAP. First, acetate hydrolysis was performed prior to hydrogenolysis of the phosphate protective groups. The acetal hydrolysis was finally catalyzed by the phosphate group itself. Second, acetate and acetal hydrolysis were performed in one single step after hydrogenolysis.
Charmantray
Franck
F
Laboratoire SEESIB, UMR 6504 CNRS, Université Blaise Pascal, 24 avenue des Landais, 63177 Aubière Cedex, France.
El Blidi
Lahssen
L
Gefflaut
Thierry
T
Hecquet
Laurence
L
Bolte
Jean
J
Lemaire
Marielle
M