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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/09/12 18:09:32」(JST)

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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]}

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

File:WP534.png

Glycolysis and Gluconeogenesis edit

^ 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

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

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 幼児および小児における低血糖症の病因 etiology of hypoglycemia in infants and children
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English Journal

In vivo and in vitro antidiabetic effects of aqueous cinnamon extract and cinnamon polyphenol-enhanced food matrix.

Cheng DM, Kuhn P, Poulev A, Rojo LE, Lila MA, Raskin I.SourceRutgers University, School of Environmental and Biological Sciences, Foran Hall, 59 Dudley Road, New Brunswick, NJ 08901, USA. Electronic address: cheng@aesop.rutgers.edu.
Food chemistry.Food Chem.2012 Dec 15;135(4):2994-3002. doi: 10.1016/j.foodchem.2012.06.117. Epub 2012 Jul 14.
Cinnamon has a long history of medicinal use and continues to be valued for its therapeutic potential for improving metabolic disorders such as type 2 diabetes. In this study, a phytochemically-enhanced functional food ingredient that captures water soluble polyphenols from aqueous cinnamon extract
PMID 22980902

Genotypic and Phenotypic Evaluation of the Evolution of High-Level Daptomycin Nonsusceptibility in Vancomycin-Resistant Enterococcus faecium.

Humphries RM, Kelesidis T, Tewhey R, Rose WE, Schork N, Nizet V, Sakoulas G.SourceDepartment of Pathology & Laboratory Medicine, David Geffen School of Medicine, University of California Los Angeles, Los Angeles, California, USA.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2012 Nov;56(11):6051-3. doi: 10.1128/AAC.01318-12. Epub 2012 Sep 4.
Whole-genome sequencing and cell membrane studies of three clonal Enterococcus faecium strains with daptomycin MICs of 4, 32, and 192 μg/ml were performed, revealing nonsynonymous single nucleotide variants in eight open reading frames, including those predicted to encode a phosphoenolpyruvate-depe
PMID 22948885

Japanese Journal

The effect of drought on photosynthetic plasticity in Marrubium vulgare plants growing at low and high altitudes

Journal of plant research 128(6), 987-994, 2015-11
NAID 40020644507

Discovery of PPi-type Phosphoenolpyruvate Carboxykinase Genes in Eukaryotes and Bacteria

The journal of biological chemistry 290(39), 23960-23970, 2015-09
NAID 120005671097

大腸菌走化性制御に関与する糖輸送系因子Enzyme Iの細胞内局在

法政大学大学院紀要（理工学・工学研究科編） (56), 2015-03-24
NAID 120005616101

Related Pictures

★リンクテーブル★

リンク元	「解糖系」「ホスホエノールピルビン酸」「PEP」
拡張検索	「GTP-dependent phosphoenolpyruvate carboxykinase」「phosphoenolpyruvate kinase」「ATP-dependent phosphoenolpyruvate carboxykinase」「phosphoenolpyruvate carboxykinase」

「解糖系」

Phosphoenolpyruvic acid
Names
	IUPAC name 2-(phosphonooxy)acrylic acid
	Other names Phosphoenolpyruvic acid, PEP
Identifiers
CAS Number	138-08-9
ChEBI	CHEBI:44897
ChemSpider	980
DrugBank	DB01819
IUPHAR/BPS	4692
Jmol 3D model	Interactive image
PubChem	1005
	InChI InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8) Key: DTBNBXWJWCWCIK-UHFFFAOYSA-N ;
	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).
	verify (what is ?)
	Infobox references

　　[★]

英: glycolytic pathway
同: エムデン-マイヤーホフ経路 Embden-Meyerhof pathway
関: 解糖、TCA回路

CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2OH)H-O- グルコース (OHが↓↓↑↓↑)
CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- グルコース-6-リン酸 (OHが↓↓↑↓↑)
C(CH2OH)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-6-リン酸
C(CH2O-PO3)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-1,6-リン酸

glucose
↓-hexokinase/glucokinase(liver)
glucose 6-phosphate
↓-phosphohexose isomerase
fructose 6-phosphate
↓-phosphofructokinase
fructose 1,6-bisphosphate
↓-aldolase
glyceraldehyde 3-phosphate
↓-glyceraldehyde-3-phosphate dehydrogenase
1,3-bisphosphoglycerate
↓-phosphoglycerate kinase →ATP
3-phosphoglycerate
↓-phosphoglyceate mutase
2-phosphoglycerate
↓-enolase
phosphoenolpyruvate
↓-pyruvate kinase → ATP
pyruvate
　－(pyruvate dehydrogenase)→acetyl-CoA
　－(pyruvate carboxylase)→oxaloacetate－(NADH+H+)→malate

解糖系の酵素 (first aid step1 2006 p.87, FASTEP1_87_酵素一覧.xls)

1	galactokinase	キナーゼ
2	galactose-1-phosphate uridyltransferase	転移酵素
3	hexokinase/glucokinase	キナーゼ
4	glucose-6-phosphatase	ホスファターゼ
5	glucose-6-phosphate dehydrogenase	脱水素酵素
6	transketolase
7	phosphofructokinase	キナーゼ
8	fructose-1,6-bisphosphatase	ホスファターゼ
9	fructokinase	キナーゼ	フルクトキナーゼ
10	aldolase B		アルドラーゼ
11	pyruvate kinase	キナーゼ	ピルビン酸キナーゼ
12	pyruvate dehydrogenase	脱水素酵素	ピルビン酸デヒドロゲナーゼ
13	HMG-CoA reductase	還元酵素	HMG-CoA還元酵素
14	pyruvate carboxylase	カルボキシラーゼ	ピルビン酸カルボキシラーゼ
15	PEP carboxykinase	キナーゼ	PEPカルボキシキナーゼ
16	citrate synthase	合成酵素	クエン酸合成酵素
17	α-ketoglutarate dehydrogenase	脱水素酵素	α-ケトグルタミン酸脱水素酵素
18	ornithine transcarbamylase	転移酵素	オルニチンカルバモイルトランスフェラーゼ

「ホスホエノールピルビン酸」

　　[★]

英: phosphoenolpyruvate phosphoenlpyruvic acid PEP

構造

CH₂-C(OH₂PO₃)-COOH

反応

ピルビン酸合成 (ホスホエノールピルビン酸 + ADP　→ ピルビン酸 + ATP)

CH₂-C(OPO₃^2-)-COOH + ADP + H⁺ －(ピルビン酸キナーゼ)→  CH₃-CO-COO^- + ATP

糖新生(オキサロ酢酸 + GTP → ホスホエノールピルビン酸 )

 HOOC-CH₂-CO-COOH + GTP －(PEPカルボキシキナーゼ)→CH₂-C(OPO₃^2-)-COOH + GDP + CO₂

「PEP」

　　[★]

？子宮外妊娠存続症

「GTP-dependent phosphoenolpyruvate carboxykinase」

　　[★]

GTP依存性ホスホエノールピルビン酸カルボキシキナーゼ

関: phosphoenolpyruvate carboxykinase

phosphoenolpyruvate carboxykinase

「phosphoenolpyruvate kinase」

　　[★] ピルビン酸キナーゼ。ホスホエノールピルビン酸キナーゼ

「ATP-dependent phosphoenolpyruvate carboxykinase」

　　[★]

ATP依存性ホスホエノールピルビン酸カルボキシキナーゼ

「phosphoenolpyruvate carboxykinase」

　　[★]

同: PEPCK

同: PEPCK

[WikiPathways-2] The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

[1] "InterPro: IPR008209 Phosphoenolpyruvate carboxykinase, GTP-utilising". Retrieved 2007-08-17.

[3] "BioCarta - Charting Pathways of Life". Retrieved 2007-08-17.

匿名

検索

案内

案内

phosphoenolpyruvate