dihydroxyacetone phosphate
{{redirect|DHAP|other uses|DHAP (chemotherapy)|and|Dhap (disambiguation)}}
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 470455047
|Name = Dihydroxyacetone phosphate
|ImageFile = Dihydroxyacetonphosphat Skelett.svg
|ImageClass = skin-invert
|ImageSize = 200px
|ImageName = Dihydroxyacetone phosphate
|PIN = 3-Hydroxy-2-oxopropyl phosphate
|OtherNames = Dihydroxyacetone phosphate
DHAP
|Section1 = {{Chembox Identifiers
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 57-04-5
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = T7KF2T6W95
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C00111
|ChEBI_Ref = {{ebicite|changed|EBI}}
|ChEBI = 57642
|PubChem = 668
|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
|ChemSpiderID = 648
|SMILES = C(C(=O)COP(=O)(O)O)O
|InChI = 1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
|InChIKey = GNGACRATGGDKBX-UHFFFAOYAZ
|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
|StdInChI = 1S/C3H5O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
|StdInChIKey = GNGACRATGGDKBX-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
|Formula = C3H7O6P
|MolarMass = 170.06 g/mol
}}
}}
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.{{cite book |last=Berg |first=Jeremy M. |author2=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=W.H. Freeman and Company |location=New York |isbn=0-7167-3051-0 |url=https://archive.org/details/biochemistrychap00jere |url-access=registration }}Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}. It is the phosphate ester of dihydroxyacetone.
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.
{{Complex enzymatic reaction
|major_substrate_1=β-D-fructose 1,6-bisphosphate
|major_substrate_1_stoichiometric_constant=
|major_substrate_1_image=beta-D-fructose-1,6-bisphosphate_wpmp.svg
|major_substrate_2=
|major_substrate_2_stoichiometric_constant=
|major_substrate_2_image=
|major_product_1=D-glyceraldehyde 3-phosphate
|major_product_1_stoichiometric_constant=
|major_product_1_image=D-glyceraldehyde-3-phosphate_wpmp.png
|major_product_2=dihydroxyacetone phosphate
|major_product_2_stoichiometric_constant=
|major_product_2_image=glycerone-phosphate_wpmp.svg
|forward_enzyme=fructose-bisphosphate aldolase
|reverse_enzyme=
|reaction_direction_(forward/reversible/reverse)=reversible
|minor_forward_substrate(s)=
|minor_forward_product(s)=
|minor_reverse_product(s)=
|minor_reverse_substrate(s)=
}}
{{KEGG compound|C05378}} {{KEGG enzyme|4.1.2.13}} {{KEGG compound|C00111}} {{KEGG compound|C00118}}
The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.
{{Enzymatic Reaction
|forward_enzyme=triose phosphate isomerase
|reverse_enzyme=
|substrate=Dihydroxyacetone phosphate
|product=D-glyceraldehyde 3-phosphate
|reaction_direction_(forward/reversible/reverse)=reversible
|minor_forward_substrate(s)=
|minor_forward_product(s)=
|minor_reverse_substrate(s)=
|minor_reverse_product(s)=
|substrate_image=glycerone-phosphate_wpmp.svg
|product_image=D-glyceraldehyde-3-phosphate_wpmp.png
}}
{{KEGG compound|C00111}}{{KEGG enzyme|5.3.1.1}}{{KEGG compound|C00118}}
{{GlycolysisGluconeogenesis_WP534|highlight=Dihydroxyacetone_phosphate}}
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.{{Ullmann|title=Propanediols|author=Carl J. Sullivan, Anja Kuenz, Klaus‐Dieter Vorlop|year=2018|doi=10.1002/14356007.a22_163.pub2}}