3-Phosphoglyceric acid

3-Phosphoglyceric acid


IUPAC name (2R)-2-Hydroxy-3-phosphonooxypropanoic acid
Identifiers
CAS number	820-11-1^N
PubChem	439183
ChemSpider	388326^Y
ChEBI	CHEBI:17794^Y
ChEMBL	CHEMBL1160563^Y
Jmol-3D images	Image 1
SMILES C([C@H](C(=O)O)O)OP(=O)(O)O
InChI InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1^Y Key: OSJPPGNTCRNQQC-UWTATZPHSA-N^Y
Properties
Molecular formula	C₃H₇O₇P
Molar mass	186.06 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3-Phosphoglyceric acid (3PG), or glycerate 3-phosphate (GP), is a biochemically significant 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle.^{[citation needed]} This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, 3-Phosphoglycerate is the product of the spontaneous split of an unstable 6-carbon intermediate formed by CO₂ fixation. Thus, two 3-phosphoglycerate molecules are produced for each molecule of CO₂ fixed.

Glycolysis

1,3-bisphospho-D-glycerate	3-phosphoglycerate kinase		3-phospho-D-glycerate	Phosphoglyceromutase	2-phospho-D-glycerate

	ADP	ATP

	ADP	ATP

	3-phosphoglycerate kinase			Phosphoglyceromutase

Compound C00236 at KEGG Pathway Database. Enzyme 2.7.2.3 at KEGG Pathway Database. Compound C00197 at KEGG Pathway Database. Enzyme 5.4.2.1 at KEGG Pathway Database. Compound C00631 at KEGG Pathway Database.

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

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Glycolysis and Gluconeogenesis edit

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

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Calvin cycle

In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (PGAL). This is the first compound formed during the C3 or Calvin cycle. It is a reactive biomolecule that is easily reduced.

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Amino acid synthesis

Glycerate 3-phosphate is also a precursor for serine, which, in turn, can create cysteine and glycine through the homocysteine cycle.

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Notes

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

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Aminoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Ornithine Putrescine Agmatine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetate

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

Glycinergics

Receptor
ligands

Agonists	Alanine Cycloserine Dimethylglycine Glycine Hypotaurine Methylglycine (Sarcosine) Milacemide Quisqualamine Serine Taurine Trimethylglycine (Betaine)

Antagonists	Bicuculline Brucine Caffeine Picrotoxin Pitrazepin Strychnine Thiocolchicoside Tutin

Reuptake
inhibitors

Plasmalemmal

GlyT1 inhibitors	Ethanol

GlyT2 inhibitors	Ethanol

Vesicular

VIAAT Inhibitors

Enzyme
inhibitors

Anabolism/Catabolism

SHMT Inhibitors

GDC Inhibitors

DAAO Inhibitors

Others

Precursors	3-Phosphoglyceric acid Serine

Cofactors	Vitamin B6 (Pyridoxine pyridoxamine pyridoxal → pyridoxal phosphate)

This article about metabolism is a stub. You can help Wikipedia by expanding it.

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Last modified on 26 April 2013, at 21:43

3-Phosphoglyceric acid

Glycolysis

Calvin cycle

Amino acid synthesis

See also

Notes

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