View source for Dihydroxyacetone phosphate

{{redirect|DHAP|chemotherapy regimen|DHAP (chemotherapy)}}
{{chembox
|Verifiedfields = changed
|Watchedfields  = changed
|verifiedrevid  = 470455047
|Name = Dihydroxyacetone phosphate
|ImageFile = Dihydroxyacetonphosphat Skelett.svg
|ImageSize = 200px
|ImageName = Dihydroxyacetone phosphate
|PIN = 3-Hydroxy-2-oxopropyl phosphate
|OtherNames = Dihydroxyacetone phosphate<br />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 = C<sub>3</sub>H<sub>7</sub>O<sub>6</sub>P
|MolarMass = 170.06 g/mol
}}
}}

'''Dihydroxyacetone phosphate''' ('''DHAP''', also '''glycerone phosphate''' in older texts) is the anion with the formula HOCH<sub>2</sub>C(O)CH<sub>2</sub>OPO<sub>3</sub><sup>2-</sup>.  This anion is involved in many [[metabolic pathway]]s, including the [[Calvin cycle]] in plants and [[glycolysis]].<ref>{{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 }}</ref><ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}.</ref> 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-<small>D</small>-[[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=<small>D</small>-[[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=<small>D</small>-[[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 [[Glycerol 3-phosphate|<small>L</small>-glycerol-3-phosphate]], which is part of the entry of [[glycerol]] (sourced from [[triglycerides]]) into the [[glycolysis|glycolytic pathway]]. Conversely, reduction of glycolysis-derived DHAP to <small>L</small>-glycerol-3-phosphate provides [[adipose cell]]s with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme [[Glycerol-3-phosphate dehydrogenase|glycerol 3-phosphate dehydrogenase]] with [[Nicotinamide adenine dinucleotide|NAD<sup>+</sup>]]/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|1,2-propanediol]].<ref name=Ullmann>{{Ullmann|title=Propanediols|author=Carl J. Sullivan, Anja Kuenz, Klaus‐Dieter Vorlop|year=2018|doi=10.1002/14356007.a22_163.pub2}}</ref>

==See also==
* [[Dihydroxyacetone]]
* [[Glycerol 3-phosphate shuttle]]

==References==
<references />

{{Glycolysis}}

[[Category:Photosynthesis]]
[[Category:Alpha-hydroxy ketones]]
[[Category:Organophosphates]]
[[Category:Phosphate esters]]
[[Category:Glycolysis]]
[[Category:Biomolecules]]
[[Category:Metabolic intermediates]]