Glyceraldehyde 3-phosphate 1437415 219862567 2008-06-17T05:18:06Z SieBot 4005189 robot Adding: [[he:גליצראלדהיד 3-פוספט]] {{Chembox new |ImageFile=G3P-2D-skeletal.png |ImageFile2=G3P-3D-balls.png |ImageSize=150px |ImageSize2=150px |IUPACName=(2-hydroxy-3-oxo-propoxy)phosphonic acid |OtherNames= |Section1= {{Chembox Identifiers | CASNo=142-10-9 | PubChem=729 | SMILES=C(C(C=O)O)OP(=O)(O)O | MeSHName=Glyceraldehyde+3-Phosphate }} |Section2= {{Chembox Properties | Formula=C<sub>3</sub>H<sub>7</sub>O<sub>6</sub>P | MolarMass=170.058 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3= {{Chembox Hazards | MainHazards= | FlashPt= | Autoignition= }} }} '''Glyceraldehyde 3-phosphate''', also known as '''triose phosphate''' or '''3-phosphoglyceraldehyde''' and abbreviated as '''G3P''', '''GADP''', '''GAP''' or '''PGAL''', is a [[chemical compound]] that occurs as an intermediate in several central [[metabolic pathway]]s of all organisms. It is a [[Phosphoric acids and Phosphates|phosphate ester]] of the 3-carbon sugar [[glyceraldehyde]] and has [[chemical formula]] [[Carbon|C]]<sub>3</sub>[[Hydrogen|H]]<sub>7</sub>[[Oxygen|O]]<sub>6</sub>[[Phosphorus|P]]. The [[CAS number]] of glyceraldehyde 3-phosphate is 142-10-9 and that of D-glyceraldehyde 3-phosphate (one of the two [[Chirality (chemistry)|optical isomers]] of the compound and the one most often occurring in living organisms) is 591-57-1. ==An intermediate in both [[glycolysis]] and [[gluconeogenesis]]== ===Formation=== D-glyceraldehyde 3-phosphate is formed from the following three compounds in reversible reactions: *'''Fructose-1,6-bisphosphate ([[F1,6BP]]), catalyzed by [[aldolase]].''' {{ 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.'' *'''Dihydroxyacetone phosphate ([[DHAP]]), catalyzed by [[triose phosphate isomerase]].''' {{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}} *'''1,3-bisphosphoglycerate ([[1,3BPG]]), catalyzed by [[glyceraldehyde 3-phosphate dehydrogenase]].''' ===As a substrate=== *'''To produce [[1,3-bisphospho-D-glycerate]] in [[glycolysis]].''' {{Enzymatic Reaction |foward_enzyme=[[glyceraldehyde phosphate dehydrogenase]] |reverse_enzyme= |substrate=[[glyceraldehyde 3-phosphate]] |product=<small>D</small>-[[glycerate 1,3-bisphosphate]] |reaction_direction_(foward/reversible/reverse)=reversible |minor_foward_substrate(s)=NAD<sup>+</sup> '''+''' P<sub>i</sub> |minor_foward_product(s)=NADH '''+''' H<sup>+</sup> |minor_reverse_substrate(s)=NADH '''+''' H<sup>+</sup> |minor_reverse_product(s)=NAD<sup>+</sup> '''+''' P<sub>i</sub> |substrate_image=D-glyceraldehyde-3-phosphate_wpmp.png |product_image=1,3-bisphospho-D-glycerate_wpmp.png }} {{KEGG compound|C00118}} {{KEGG enzyme|1.2.1.12}} {{KEGG reaction|R01063}} {{KEGG compound|C00236}} D-glyceraldehyde 3-phosphate is also of some importance since this is how [[glycerol]] (as DHAP) enters the glycolytic and gluconeogenetic pathways. Furthermore, it is a participant in and a product of the [[pentose phosphate pathway]]. ==An intermediate in [[photosynthesis]]== During plant [[photosynthesis]], two molecules of [[glycerate 3-phosphate]] (GP) are produced by the first step of the [[light-independent reaction]]s when [[ribulose 1,5-bisphosphate]] (RuBP) and [[carbon dioxide]] are catalysed by the [[rubisco]] enzyme. The GP is converted to D-glyceraldehyde 3-phosphate using the energy in [[Adenosine triphosphate|ATP]] and the reducing power of [[NADPH]] as part of the [[Calvin cycle]]. This returns [[Adenosine diphosphate|ADP]], phosphate ions Pi, and [[NADP]]+ to the [[light-dependent reaction]]s of photosynthesis for their continued functioning. RuBP is regenerated for the Calvin cycle to continue. G3P is generally considered the prime end-product of photosynthesis and it can be used as an immediate food nutrient, combined and rearranged to form monosaccharide sugars, such as [[glucose]], which can be transported to other cells, or packaged for storage as insoluble [[polysaccharide]]s such as [[starch]]. ===Balance sheet=== 6 CO<sub>2</sub> + 6 '''RuBP''' (+ energy from 12 [[Adenosine triphosphate|ATP]] and 12 NADPH) → 12 '''G3P''' (3-carbon) 10 '''G3P''' (+ energy from 6 [[Adenosine triphosphate|ATP]]) → 6 '''RuBP''' (ie starting material regenerated) 2 '''G3P''' → [[glucose]] (6-carbon). ==In [[tryptophan]] biosynthesis== Glyceradehyde 3-phosphate occurs as a byproduct in the biosynthesis pathway of [[tryptophan]], an essential [[amino acid]] that cannot be produced by the human body. ==In [[thiamine]] biosynthesis== Glyceraldehyde 3-phosphate occurs as a reactant in the biosynthesis pathway of [[thiamine]] (Vitamin B<sub>1</sub>), another substance that cannot be produced by the human body. ==See also== {{Glycolysis}} == External links == * [http://www.genome.jp/dbget-bin/www_bget?compound+C00118 D-Glyceraldehyde 3-phosphate and the reactions and pathways it participates in], from the [[KEGG PATHWAY Database]] * [http://www.genome.jp/dbget-bin/www_bget?compound+C00661 Glyceraldehyde 3-phosphate and the reactions and pathways it participates in], from the KEGG PATHWAY Database {{metabolism-stub}} [[Category:Photosynthesis]] [[Category:Organophosphates]] [[fr:Glycéraldéhyde-3-phosphate]] [[it:Gliceraldeide-3-fosfato]] [[he:גליצראלדהיד 3-פוספט]] [[ja:グリセルアルデヒド-3-リン酸]] [[zh:甘油醛-3-磷酸]]