Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis. It is the phosphate ester of dihydroxyacetone.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||170.06 g/mol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Role in glycolysisEdit
Dihydroxyacetone phosphate lies in the glycolysis metabolic pathway, and is one of the two products of breakdown of fructose 1,6-bisphosphate, along with glyceraldehyde 3-phosphate. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate.
|β-D-fructose 1,6-bisphosphate||fructose-bisphosphate aldolase||D-glyceraldehyde 3-phosphate||dihydroxyacetone phosphate|
The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.
|Dihydroxyacetone phosphate||triose phosphate isomerase||D-glyceraldehyde 3-phosphate|
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Role in other pathwaysEdit
In the Calvin cycle, DHAP is one of the products of the sixfold reduction of 1,3-bisphosphoglycerate by NADPH. It is also used in the synthesis of sedoheptulose 1,7-bisphosphate and fructose 1,6-bisphosphate, both of which are used to reform ribulose 5-phosphate, the 'key' carbohydrate of the Calvin cycle.
DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate, which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor.
DHAP also has a role in the ether-lipid biosynthesis process in the protozoan parasite Leishmania mexicana.