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Glyceraldehyde 3-phosphate

From Wikipedia, the free encyclopedia
Not to be confused withglycerol 3-phosphate orglycerate 3-phosphate.
Glyceraldehyde 3-phosphate
Names
IUPAC name
2-hydroxy-3-oxopropyl dihydrogen phosphate
Identifiers
3D model (JSmol)
1725008
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.008.839Edit this at Wikidata
EC Number
  • 209-721-7
KEGG
MeSHGlyceraldehyde+3-Phosphate
UNII
  • InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8) checkY
    Key: LXJXRIRHZLFYRP-UHFFFAOYSA-N checkY
  • InChI=1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
    Key: LXJXRIRHZLFYRP-UHFFFAOYAH
  • C([C@H](C=O)O)OP(=O)(O)O
Properties
C3H7O6P
Molar mass170.058
Melting point102–104 °C[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Glyceraldehyde 3-phosphate, also known astriose phosphate or3-phosphoglyceraldehyde and abbreviated asG3P,GA3P,GADP,GAP,TP,GALP orPGAL, is ametabolite that occurs as an intermediate in several centralpathways of all organisms.[2][3] With thechemical formula H(O)CCH(OH)CH2OPO32-, this anion is amonophosphate ester ofglyceraldehyde.

An intermediate in both glycolysis and gluconeogenesis

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Formation

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D-glyceraldehyde 3-phosphate is formed from the following three compounds in reversible reactions:

β-D-fructose 1,6-bisphosphatefructose-bisphosphate aldolaseD-glyceraldehyde 3-phosphatedihydroxyacetone phosphate
+
fructose-bisphosphate aldolase

CompoundC05378 atKEGG Pathway Database.Enzyme4.1.2.13 atKEGG Pathway Database.CompoundC00111 atKEGG Pathway Database.CompoundC00118 atKEGG Pathway Database.

The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.

Dihydroxyacetone phosphatetriose phosphate isomeraseD-glyceraldehyde 3-phosphate
 
 
 triose phosphate isomerase

CompoundC00111 atKEGG Pathway Database.Enzyme5.3.1.1 atKEGG Pathway Database.CompoundC00118 atKEGG Pathway Database.

As a substrate

[edit]
glyceraldehyde 3-phosphateglyceraldehyde phosphate dehydrogenaseD-glycerate 1,3-bisphosphate
 
NAD++ PiNADH+ H+
NAD++ PiNADH+ H+

CompoundC00118 atKEGG Pathway Database.Enzyme1.2.1.12 atKEGG Pathway Database.ReactionR01063 atKEGG Pathway Database.CompoundC00236 atKEGG Pathway Database.

D-glyceraldehyde 3-phosphate is also of some importance since this is howglycerol (as DHAP) enters the glycolytic and gluconeogenic pathways. Furthermore, it is a participant in and a product of thepentose phosphate pathway.

Interactive pathway map

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|Click on genes, proteins and metabolites below to link to respective articles.[§ 1]

  1. ^The interactive pathway map can be edited at WikiPathways:"GlycolysisGluconeogenesis_WP534".

An intermediate in photosynthesis

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During plantphotosynthesis, 2 equivalents ofglycerate 3-phosphate (GP; also known as 3-phosphoglycerate) are produced by the first step of thelight-independent reactions whenribulose 1,5-bisphosphate (RuBP) andcarbon dioxide are catalysed by therubisco enzyme. The GP is converted to D-glyceraldehyde 3-phosphate (G3P) using the energy inATP and the reducing power ofNADPH as part of theCalvin cycle. This returnsADP, phosphate ions Pi, andNADP+ to thelight-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 asglucose, which can be transported to other cells, or packaged for storage as insolublepolysaccharides such asstarch.

Balance sheet

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6 CO2 + 6RuBP (+ energy from 12ATP and 12 NADPH) →12G3P (3-carbon)

10G3P (+ energy from 6ATP) → 6RuBP (i.e. starting material regenerated)

2G3Pglucose (6-carbon).

In tryptophan biosynthesis

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Glyceraldehyde 3-phosphate occurs as a byproduct in the biosynthesis pathway oftryptophan, an essentialamino acid that cannot be produced by the human body.

In thiamine biosynthesis

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Glyceraldehyde 3-phosphate occurs as a reactant in the biosynthesis pathway ofthiamine (Vitamin B1), another substance that cannot be produced by the human body.

References

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  1. ^"metabocard for Glycerol 3-phosphate".
  2. ^Berg, Jeremy M.; Tymoczko, Stryer (2002).Biochemistry (5th ed.). New York:W.H. Freeman and Company.ISBN 0-7167-3051-0.
  3. ^Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000.ISBN 1-57259-153-6.

External links

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Wikimedia Commons has media related toGlyceraldehyde 3-phosphate.
Fructose
Galactose
Mannose
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