Dihydroxyacetone phosphate

"DHAP" redirects here. For chemotherapy regimen, see DHAP (chemotherapy).
Dihydroxyacetone phosphate
Names
IUPAC name
3-Hydroxy-2-oxopropyl phosphate
Other names
Dihydroxyacetone phosphate
DHAP
Identifiers
57-04-5 
ChEBI CHEBI:57642 
ChemSpider 648 
Jmol-3D images Image
PubChem 668
Properties
C3H7O6P
Molar mass 170.06 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
  verify (what is: Yes/?)
Infobox references

Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is a biochemical compound involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis.

Role in glycolysis

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
+

Compound C05378 at KEGG Pathway Database. Enzyme 4.1.2.13 at KEGG Pathway Database. Compound C00111 at KEGG Pathway Database. Compound C00118 at KEGG Pathway Database.

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
 
 
 

Compound C00111 at KEGG Pathway Database.Enzyme 5.3.1.1 at KEGG Pathway Database.Compound C00118 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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Glycolysis and Gluconeogenesis edit

  1. The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Role 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, 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.

See also