Dihydroxyacetone phosphate

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Dihydroxyacetone phosphate
IUPAC name	1,3-Dihydroxy-2-propanone phosphate
Other names	Dihydroxyacetone phosphate DHAP
Identifiers
CAS Number	57-04-5
3D model (JSmol)	Interactive image
ECHA InfoCard
SMILES OCC(COP(O)(O)=O)=O
Properties
Chemical formula	C3H7O6P
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
				+
	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
	{{{minor_forward_substrate(s)}}}	{{{minor_forward_product(s)}}}
	[[image:Biochem_reaction_arrow_{{{reaction_direction_(forward/reversible/reverse)}}}_NNNN_horiz_med.svg|75px]]
	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

• Dihydroxyacetone