Glyceraldehyde 3-phosphate

Glyceraldehyde 3-phosphate
Names


IUPAC name 2-hydroxy-3-oxopropyl dihydrogen phosphate
Identifiers
CAS Number	591-59-3^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17138^Y
ChemSpider	709 (Racemic)^Y 393755 (L isomer)^Y 388314 (D isomer)^Y
KEGG	C00661^Y
MeSH	Glyceraldehyde+3-Phosphate
PubChem CID	729
InChI InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)^Y Key: LXJXRIRHZLFYRP-UHFFFAOYSA-N^Y InChI=1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8) Key: LXJXRIRHZLFYRP-UHFFFAOYAH
SMILES C([C@H](C=O)O)OP(=O)(O)O
Properties
Chemical formula	C₃H₇O₆P
Molar mass	170.058
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GA3P, GADP, GAP, TP, GALP or PGAL, is a chemical compound that occurs as an intermediate in several central metabolic pathways of all organisms. It is a phosphate ester of the 3-carbon sugar glyceraldehyde and has chemical formula C₃H₇O₆P.

The CAS number of glyceraldehyde 3-phosphate is 591-59-3 and that of D-glyceraldehyde 3-phosphate (one of the two 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.

β-D-fructose 1,6-bisphosphate	fructose-bisphosphate aldolase	D-glyceraldehyde 3-phosphate		dihydroxyacetone phosphate
			+




	fructose-bisphosphate aldolase

Compound C05378 at KEGG Pathway Database. Enzyme 4.1.2.13 at KEGG Pathway Database. Compound C00111 at KEGG Pathway Database. Compound C00118 at KEGG Pathway Database.

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.

Dihydroxyacetone phosphate	triose phosphate isomerase	D-glyceraldehyde 3-phosphate





	triose phosphate isomerase

Compound C00111 at KEGG Pathway Database.Enzyme 5.3.1.1 at KEGG Pathway Database.Compound C00118 at KEGG Pathway Database.

1,3-bisphosphoglycerate (1,3BPG), catalyzed by glyceraldehyde 3-phosphate dehydrogenase.

As a substrate

To produce 1,3-bisphospho-D-glycerate in glycolysis.

glyceraldehyde 3-phosphate	glyceraldehyde phosphate dehydrogenase		D-glycerate 1,3-bisphosphate

	NAD⁺ + P_i	NADH + H⁺

	NAD⁺ + P_i	NADH + H⁺

Compound C00118 at KEGG Pathway Database. Enzyme 1.2.1.12 at KEGG Pathway Database. Reaction R01063 at KEGG Pathway Database. Compound C00236 at KEGG Pathway Database.

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

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

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|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit]]

Glycolysis and Gluconeogenesis edit

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

An intermediate in photosynthesis

During plant photosynthesis, 2 molecules 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

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

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

2 G3P → glucose (6-carbon).

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

External links

Wikimedia Commons has media related to Glyceraldehyde 3-phosphate.

D-Glyceraldehyde 3-phosphate and the reactions and pathways it participates in, from the KEGG PATHWAY Database
Glyceraldehyde 3-phosphate and the reactions and pathways it participates in, from the KEGG PATHWAY Database

Glycolysis metabolic pathway

Glucose	Hexokinase		Glucose 6-phosphate	Glucose-6-phosphate isomerase	Fructose 6-phosphate	phosphofructokinase-1		Fructose 1,6-bisphosphate	Fructose-bisphosphate aldolase
	ATP	ADP				ATP	ADP

Dihydroxyacetone phosphate		Glyceraldehyde 3-phosphate	Triosephosphate isomerase		Glyceraldehyde 3-phosphate	Glyceraldehyde-3-phosphate dehydrogenase			1,3-Bisphosphoglycerate
						NAD⁺ + P_i	NADH + H⁺
	+			2				2

Phosphoglycerate kinase

3-Phosphoglycerate

Phosphoglycerate mutase

2-Phosphoglycerate

Phosphopyruvate hydratase(Enolase)

Phosphoenolpyruvate

Pyruvate kinase

Pyruvate

ADP

ATP

H₂O

ADP

ATP

Fructose and galactose metabolic intermediates

Fructose

Fructose-1-phosphate → DHAP/Glyceraldehyde → Glyceraldehyde 3-phosphate

Galactose

Galactose-1-phosphate → Glucose 1-phosphate → Glucose 6-phosphate → Fructose 6-phosphate
Uridine diphosphate galactose Uridine diphosphate glucose
Galactitol Iditol

Mannose

Mannose-6-phosphate → Fructose 6-phosphate

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