Dihydroxyacetone phosphate
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210655082
2008-05-06T20:57:41Z
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changing stub name per [[Wikipedia:Stub_types_for_deletion/Log/2008/March/19|SfD]] using [[Project:AutoWikiBrowser|AWB]]
{{Unreferenced|date =September 2007}}
{{Chembox new
| Name = Dihydroxyacetone phosphate
| ImageFile = DHAP.png
<!-- | ImageSize = 200px -->
| ImageName = Dihydroxyacetone phosphate
| IUPACName = 1,3-Dihydroxy-2-propanone phosphate
| OtherNames = Dihydroxyacetone phosphate<br />DHAP
| Section1 = {{Chembox Identifiers
| CASNo = 57-04-5
| SMILES = OCC(COP(O)(O)=O)=O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>3</sub>H<sub>7</sub>O<sub>6</sub>P
| MolarMass = 170.06 g/mol
| MeltingPt =
}}
}}
'''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.
{{ Complex Enzymatic Reaction
|major_substrate_1=β-<small>D</small>-[[fructose 1,6-phosphate]]
|major_substrate_1_stoichiometric_constant=
|major_substrate_1_image=beta-D-fructose-1,6-bisphosphate_wpmp.png
|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.png
|foward_enzyme=[[fructose bisphosphate aldolase]]
|reverse_enzyme=[[fructose bisphosphate aldolase]]
|reaction_direction_(foward/reversible/reverse)=reversible
|minor_foward_substrate(s)=
|minor_foward_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
|foward_enzyme=[[triose phosphate isomerase]]
|reverse_enzyme=[[triose phosphate isomerase]]
|substrate=Dihydroxyacetone phosphate
|product=<small>D</small>-[[glyceraldehyde 3-phosphate]]
|reaction_direction_(foward/reversible/reverse)=reversible
|minor_foward_substrate(s)=
|minor_foward_product(s)=
|minor_reverse_substrate(s)=
|minor_reverse_product(s)=
|substrate_image=glycerone-phosphate_wpmp.png
|product_image=D-glyceraldehyde-3-phosphate_wpmp.png
}}
{{KEGG compound|C00111}}{{KEGG enzyme|5.3.1.1}}{{KEGG compound|C00118}}
==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 [[Glycerol 3-phosphate|L-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 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]]<sup>+</sup>/NADH as cofactor.
==See also==
* [[Dihydroxyacetone]]
{{Glycolysis}}
{{metabolism-stub}}
[[Category:Photosynthesis]]
[[Category:Ketones]]
[[Category:Organophosphates]]
[[de:Dihydroxyacetonphosphat]]
[[it:Diidrossiacetone fosfato]]
[[ja:ジヒドロキシアセトンリン酸]]
[[zh:二羥丙酮磷酸]]