Phosphoenolpyruvic acid

Phosphoenolpyruvic acid

Names
IUPAC name 2-(phosphonooxy)acrylic acid
Other names Phosphoenolpyruvic acid, PEP
Identifiers
CAS Number	138-08-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:44897 Y
ChemSpider	980 Y
DrugBank	DB01819 Y
ECHA InfoCard	100.004.830
IUPHAR/BPS	4692
PubChem	1005
InChI InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8) Y Key: DTBNBXWJWCWCIK-UHFFFAOYSA-N Y
SMILES O=C(O)C(OP(=O)(O)O)=C
Properties
Chemical formula	C3H5O6P
Molar mass	168.042
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Phosphoenolpyruvic acid (PEP), or phosphoenolpyruvate (2-phosphoenolpyruvate) as the anion, is an important chemical compound in biochemistry. It has the highest-energy phosphate bond found (-61.9 kJ/mol) in living organisms, and is involved in glycolysis and gluconeogenesis. In plants, it is also involved in the biosynthesis of various aromatic compounds, and in carbon fixation; in bacteria, it is also used as the source of energy for the phosphotransferase system.

In glycolysis

PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells.

2-phospho-D-glycerate	Enolase		phosphoenolpyruvate	Pyruvate kinase		pyruvate
		H2O		ADP	ATP
		H2O
	Enolase			Pyruvate kinase

Compound C00631 at KEGG Pathway Database. Enzyme 4.2.1.11 at KEGG Pathway Database. Compound C00074 at KEGG Pathway Database. Enzyme 2.7.1.40 at KEGG Pathway Database. Compound C00022 at KEGG Pathway Database.

In gluconeogenesis

PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of one guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis:^[1]

GTP + oxaloacetate → GDP + phosphoenolpyruvate + CO₂

Interactive pathway map

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

[[File:

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:828px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.6666666666666px; height:0px; overflow:hidden; position:relative; left:695.6666666666667px; top:1197px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:801.0px; top:1029.66666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:555.3333333333333px; top:991.166666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:386.0px; top:594px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:723.0px; top:1086px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.0px; top:140.655462184874px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.9999999999999px; top:882.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:477.6500000000001px; top:942.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.99999999999994px; top:432.616246498599px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:384.8991596638656px; top:277.627450980392px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.0px; top:200.655462184874px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:390.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.6666666666666px; height:0px; overflow:hidden; position:relative; left:695.6666666666667px; top:1237px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.99999999999994px; top:502.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:555.3333333333333px; top:891.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:322.9999999999999px; top:981.666666666668px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.6666666666666px; height:0px; overflow:hidden; position:relative; left:695.6666666666667px; top:1137px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:103.366666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:315.274509803922px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.6666666666666px; height:0px; overflow:hidden; position:relative; left:695.6666666666667px; top:1157px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:657.9999999999997px; top:992.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:749px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.9999999999999px; top:696.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.9999999999999px; top:843.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.99999999999994px; top:412.616246498599px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:801.0000000000001px; top:945.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.9999999999999px; top:862.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:223.366666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.6666666666666px; height:0px; overflow:hidden; position:relative; left:695.6666666666667px; top:1177px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.99999999999994px; top:542.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:801.0px; top:844px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:470px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:894.366666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:872.3333333333333px; top:893.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:477.6500000000001px; top:844px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.9999999999999px; top:716.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.6666666666666px; height:0px; overflow:hidden; position:relative; left:695.6666666666667px; top:1217px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:477.6500000000001px; top:1029.66666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:669px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:1033.66666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.99999999999994px; top:522.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.0px; top:180.655462184874px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:872.3333333333334px; top:992.166666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:329.33333333333303px; top:629.666666666666px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:222.5px; top:588.616666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:773.5px; top:1270.7px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.0px; top:160.655462184874px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.9999999999999px; top:349.445378151261px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:386.0px; top:120.655462184874px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:119.22128851540629px; top:246.677871148459px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:119.22128851540629px; top:306.67787114846px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:119.22128851540629px; top:286.67787114846px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:119.22128851540629px; top:266.67787114846px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:117.66666666666674px; top:425.666666666666px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:117.66666666666674px; top:405.666666666666px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:117.66666666666674px; top:445.666666666666px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.3333333333333px; height:0px; overflow:hidden; position:relative; left:125.00000000000004px; top:616.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:63.3333333333333px; height:0px; overflow:hidden; position:relative; left:125.00000000000004px; top:636.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:113.00000000000006px; top:799.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:113.00000000000006px; top:779.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:104.29411764705867px; top:952.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:104.29411764705867px; top:972.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:104.29411764705867px; top:932.333333333333px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:89.0px; top:1044.66666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:89.0px; top:1064.66666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:89.0px; top:1104.66666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:89.0px; top:1084.66666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:100px; height:0px; overflow:hidden; position:relative; left:197.3666666666667px; top:1129.36666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:193px; height:0px; overflow:hidden; position:relative; left:539.9495798319327px; top:314.941176470588px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:163px; height:0px; overflow:hidden; position:relative; left:541.9495798319327px; top:358.941176470588px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:95px; height:0px; overflow:hidden; position:relative; left:870.0px; top:1149px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:593.0px; top:1076px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:593.0px; top:1096px; background:transparent; border-top:3px blue solid"></div>]]

[[

]]

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

Glycolysis and Gluconeogenesis edit

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

In plants

PEP may be used for the synthesis of chorismate through the shikimate pathway.^[2] Chorismate may then be metabolized into the aromatic amino acids (phenylalanine, tryptophan and tyrosine) and other aromatic compounds. The first step is when Phosphoenolpyruvate and erythrose-4-phosphate react to form 3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzyme DAHP synthase.

Biosynthesis of DAHP from phosphoenolpyruate and erythrose-4-phosphate

In addition, in C₄ plants, PEP serves as an important substrate in carbon fixation. The chemical equation, as catalyzed by phosphoenolpyruvate carboxylase (PEP carboxylase), is:

PEP + HCO₃⁻ → oxaloacetate

References

1. ↑ "InterPro: IPR008209 Phosphoenolpyruvate carboxykinase, GTP-utilising". Retrieved 2007-08-17. 
2. ↑ "BioCarta - Charting Pathways of Life". Retrieved 2007-08-17. 

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+ + Pi NADH + H+ + 2 2 Phosphoglycerate kinase 3-Phosphoglycerate Phosphoglycerate mutase 2-Phosphoglycerate Phosphopyruvate hydratase(Enolase) Phosphoenolpyruvate Pyruvate kinase Pyruvate ADP ATP H2O ADP ATP 2 2 2 2