Glyceraldehyde 3-phosphate

Glyceraldehyde 3-phosphate

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IUPAC name	(2-hydroxy-3-oxo-propoxy)phosphonic acid
Identifiers
CAS number	142-10-9
PubChem	729
MeSH	Glyceraldehyde+3-Phosphate
SMILES	C(C(C=O)O)OP(=O)(O)O
Properties
Molecular formula	C₃H₇O₆P
Molar mass	170.058
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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 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 142-10-9 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-phosphate	fructose bisphosphate aldolase	D-glyceraldehyde 3-phosphate		dihydroxyacetone phosphate
			+




	fructose bisphosphate aldolase

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

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⁺

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 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 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 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 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 (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 B₁), another substance that cannot be produced by the human body.