- A NOVEL CONVENIENT PREPARATION OF DIHYDROXYACETONE PHOSPHATE AND ITS USE IN ENZYMATIC ALDOL REACTIONS
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A new preparation of the stable barium salt of 2,5-bis(phosphonooxymethyl)-2,5-diethoxy-1,4-dioxane Ba-2 is described, which by treatment with DOWEX 50 H(1+) gives dihydroxyacetone phosphate (DHAP) in high yield.DHAP prepared by this method was used for aldolase-catalyzed condensations.
- Effenberger, Franz,Straub, Alexander
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- An improved synthesis of dihydroxyacetone phosphate
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An improved procedure has been developed for the synthesis of dihydroxyacetone phosphate (DHAP). Reaction of 2,5-diethoxy-p-dioxane-2,5-dimethanol (1) and the trivalent phosphorylating reagent dibenzyl-N,N-diethylphosphoramidite (DDP) in the presence of 1,2,4-triazole or tetrazole followed by oxidation with H2O2 gave 2,5-diethoxy-p-dioxane-2,5-dimethanol-O-21-O-51-bis(phosphate) tetrabenzyl ester (2) in 98% yield. Compound 2 was then hydrogenated in the presence of H2-Pd/C to give, after neutralization, 2,5-diethoxy-p-dioxane-2,5-dimethanol-O-21-O-51-bis(phosphate) as a stable trisodium salt (3) in 84% yield. Treatment of 3 with Dowex 50 (H+) generates 2 equivalents of DHAP.
- Pederson,Esker,Wong
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p. 2643 - 2648
(2007/10/02)
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