Dihydroxyacetone phosphate

"DHAP" redirects here. For chemotherapy regimen, see DHAP (chemotherapy).

Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH₂C(O)CH₂OPO₃^2-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis.^[1][2] It is the phosphate ester of dihydroxyacetone.

Dihydroxyacetone phosphate

Names
Preferred IUPAC name 3-Hydroxy-2-oxopropyl phosphate
Other names Dihydroxyacetone phosphate DHAP
Identifiers
CAS Number	57-04-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:57642 N
ChemSpider	648 N
ECHA InfoCard	100.000.280
KEGG	C00111 Y
PubChem CID	668
UNII	T7KF2T6W95 Y
CompTox Dashboard (EPA)	DTXSID6058768
InChI InChI=1S/C3H5O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8) N Key: GNGACRATGGDKBX-UHFFFAOYSA-N N InChI=1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8) Key: GNGACRATGGDKBX-UHFFFAOYAZ
SMILES C(C(=O)COP(=O)(O)O)O
Properties
Chemical formula	C3H7O6P
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). N verify (what is YN ?) Infobox references

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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|alt=Glycolysis and Gluconeogenesis edit]]

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.

DHAP is a precursor to 2-oxopropanal. This conversion is the basis of a potential biotechnological route to the commodity chemical 1,2-propanediol.^[3]

See also

• Dihydroxyacetone
• Glycerol 3-phosphate shuttle

References

1. Berg, Jeremy M.; Tymoczko, Stryer (2002). Biochemistry (5th ed.). New York: W.H. Freeman and Company. ISBN 0-7167-3051-0.
2. Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
3. Carl J. Sullivan, Anja Kuenz, Klaus‐Dieter Vorlop (2018). "Propanediols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_163.pub2. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)