Dihydroxyacetone phosphate 1565992 210655082 2008-05-06T20:57:41Z Rockfang 5403270 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]]