Glyceraldehyde 3-phosphate
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2008-06-17T05:18:06Z
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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]]