Glyceraldehyde 3-phosphate
{{distinguish|glycerol 3-phosphate|glycerate 3-phosphate}}
{{Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 470454981
|ImageFile = D-Glycerinaldehyde 3-phosphate deprotonated V1.svg
|ImageSize = 180px
|ImageClass = skin-invert
|ImageSize2 = 180px
|IUPACName = 2-hydroxy-3-oxopropyl dihydrogen phosphate
|Section1={{Chembox Identifiers
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C00661
|KEGG1_Ref = {{keggcite|correct|kegg}}
|KEGG1 = C00118
|InChI = 1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
|InChIKey = LXJXRIRHZLFYRP-UHFFFAOYAH
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = LXJXRIRHZLFYRP-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 591-59-3
|UNII = 7466PL1110
|UNII_Ref = {{fdacite|correct|FDA}}
|PubChem = 729
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 709
|ChemSpiderID_Comment = (Racemic)
|ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID1 = 393755
|ChemSpiderID1_Comment = (L isomer)
|ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID2 = 388314
|ChemSpiderID2_Comment = (D isomer)
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 17138
|ChEMBL = 1232918
|DrugBank = DB02263
|Beilstein = 1725008
|EINECS = 209-721-7
|SMILES = C([C@H](C=O)O)OP(=O)(O)O
|MeSHName = Glyceraldehyde+3-Phosphate
}}
|Section2={{Chembox Properties
|Formula = C3H7O6P
|MolarMass = 170.058
|MeltingPt = 102–104 °C{{cite web | title=metabocard for Glycerol 3-phosphate | url=http://www.hmdb.ca/metabolites/HMDB0000126}}
}}
}}
Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GA3P, GADP, GAP, TP, GALP or PGAL, is a metabolite that occurs as an intermediate in several central pathways of all organisms.{{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 }}Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}. With the chemical formula H(O)CCH(OH)CH2OPO32-, this anion is a monophosphate ester of glyceraldehyde.
An intermediate in both glycolysis and gluconeogenesis
=Formation=
D-glyceraldehyde 3-phosphate is formed from the following three compounds in reversible reactions:
{{Complex enzymatic reaction
| major_substrate_1 = β-D-fructose 1,6-bisphosphate
| 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 = D-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
| forward_enzyme = fructose-bisphosphate aldolase
| reverse_enzyme = fructose-bisphosphate aldolase
| 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.
- Dihydroxyacetone phosphate (DHAP), catalyzed by triose phosphate isomerase.
{{Enzymatic Reaction
| forward_enzyme = triose phosphate isomerase
| reverse_enzyme = triose phosphate isomerase
| substrate = Dihydroxyacetone phosphate
| product = D-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.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
| forward_enzyme = glyceraldehyde phosphate dehydrogenase
| reverse_enzyme =
| substrate = glyceraldehyde 3-phosphate
| product = D-glycerate 1,3-bisphosphate
| reaction_direction_(forward/reversible/reverse)=reversible
| minor_forward_substrate(s)=NAD+ + Pi
| minor_forward_product(s)=NADH + H+
| minor_reverse_substrate(s)=NADH + H+
| minor_reverse_product(s)=NAD+ + Pi
| substrate_image = D-glyceraldehyde-3-phosphate_wpmp.png
| product_image = 1,3-bisphospho-D-glycerate.svg
| product_image_size = 88px
}}
{{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 gluconeogenic pathways. Furthermore, it is a participant in and a product of the pentose phosphate pathway.
= Interactive pathway map =
|{{GlycolysisGluconeogenesis_WP534|highlight=Glyceraldehyde_3-phosphate}}
An intermediate in photosynthesis
During plant photosynthesis, 2 equivalents of glycerate 3-phosphate (GP; also known as 3-phosphoglycerate) are produced by the first step of the light-independent reactions when ribulose 1,5-bisphosphate (RuBP) and carbon dioxide are catalysed by the rubisco enzyme. The GP is converted to D-glyceraldehyde 3-phosphate (G3P) using the energy in ATP and the reducing power of NADPH as part of the Calvin cycle. This returns ADP, phosphate ions Pi, and NADP+ to the light-dependent reactions of photosynthesis for their continued function.
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 polysaccharides such as starch.
=Balance sheet=
In tryptophan biosynthesis
Glyceraldehyde 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 B1), another substance that cannot be produced by the human body.
References
{{reflist}}
External links
{{Commonscat}}
- [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
{{Glycolysis}}
{{Fructose and galactose metabolic intermediates}}