Dihydroxyacetone phosphate

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Dihydroxyacetone phosphate
IUPAC name 1,3-Dihydroxy-2-propanone phosphate
Other names Dihydroxyacetone phosphate
3D model (JSmol)
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Molar mass 170.06 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dihydroxyacetone phosphate (DHAP) is a biochemical compound involved in many reactions, from the Calvin cycle in plants to the ether-lipid biosynthesis process in Leishmania mexicana. Its major biochemical role is in the glycolysis metabolic pathway. DHAP may be referred to as glycerone phosphate in older texts.

Dihydroxyacetone phosphate in glycolysis

Dihydroxyacetone phosphate lies in the glycolysis metabolic pathway, and is one of the two products of breakdown of fructose 1,6-phosphate, along with glyceraldehyde 3-phosphate. It is rapidly, reversibly, isomerised to glyceraldehyde 3-phosphate.

β-D-fructose 1,6-phosphate fructose bisphosphate aldolase D-glyceraldehyde 3-phosphate dihydroxyacetone phosphate
Beta-D-fructose-1,6-bisphosphate wpmp.png D-glyceraldehyde-3-phosphate wpmp.png + Glycerone-phosphate wpmp.png
Biochem reaction arrow reversible NNNN horiz med.png
fructose bisphosphate aldolase

The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.

Dihydroxyacetone phosphate {{{forward_enzyme}}} D-glyceraldehyde 3-phosphate
Glycerone-phosphate wpmp.png   D-glyceraldehyde-3-phosphate wpmp.png
{{{minor_forward_substrate(s)}}} {{{minor_forward_product(s)}}}
  triose phosphate isomerase

Dihydroxyacetone phosphate in other pathways

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 which are both 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-glyercol-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.

See also


External links

Template:Metabolic pathway stub

de:Dihydroxyacetonphosphat it:Diidrossiacetone fosfato