ピロリン酸 pyrophosphate inorganic pyrophosphate

WordNet

a salt or ester of pyrophosphoric acid
the 16th letter of the Roman alphabet (同)p

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parking
phosphorusの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/01 21:58:22」(JST)

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In chemistry, pyrophosphate is a phosphorus oxyanion. Compounds such as salts and esters are also called pyrophosphates. The group is also called diphosphate, short for dipolyphosphate, although this should not be confused with two phosphates. As a food additive, diphosphates are known as E450. As well as the normal pyrophosphates, a number of hydrogen pyrophosphates also exist, such as Na₂H₂P₂O₇.

Chemistry

Pyrophosphates were originally prepared by heating phosphates (pyro from the Greek, meaning "fire"). Pyrophosphates generally exhibit the highest solubilities among the phosphates;^[1] moreover, they are good complexing agents for metal ions (such as calcium and many transition metals) and have many uses in industrial chemistry. Pyrophosphate is the first member of an entire series of polyphosphates.

The term pyrophosphate is also the name of esters formed by the condensation of a phosphorylated biological compound with inorganic phosphate as for dimethylallyl pyrophosphate. This bond is also referred to as a high-energy phosphate bond.

The synthesis of tetraethyl pyrophosphate was first described in 1854 by Philippe de Clermont at a meeting of the French Academy of Sciences.

In biochemistry

Pyrophosphates are very important in biochemistry. The anion P₂O₇⁴⁻ is abbreviated PP_i and is formed by the hydrolysis of ATP into AMP in cells.

ATP → AMP + PP_i

For example, when a nucleotide is incorporated into a growing DNA or RNA strand by a polymerase, pyrophosphate (PP_i) is released. Pyrophosphorolysis is the reverse of the polymerization reaction in which pyrophosphate reacts with the 3'-nucleotidemonophosphate (NMP or dNMP), which is removed from the oligonucleotide to release the corresponding triphosphate (dNTP from DNA, or NTP from RNA).

The pyrophosphate anion has the structure P₂O₇⁴⁻, and is an acid anhydride of phosphate. It is unstable in aqueous solution and hydrolyzes into inorganic phosphate:

P₂O₇⁴⁻ + H₂O → 2 HPO₄²⁻

or in biologists' shorthand notation:

PP_i + H₂O → 2 P_i

In the absence of enzymic catalysis, hydrolysis reactions of simple polyphosphates such as pyrophosphate, linear triphosphate, ADP, and ATP normally proceed extremely slowly in all but highly acidic media.^[2]

(The reverse of this reaction is a method of preparing pyrophosphates by heating phosphates.)

This hydrolysis to inorganic phosphate effectively renders the cleavage of ATP to AMP and PP_i irreversible, and biochemical reactions coupled to this hydrolysis are irreversible as well.

PP_i occurs in synovial fluid, blood plasma, and urine at levels sufficient to block calcification and may be a natural inhibitor of hydroxyapatite formation in extracellular fluid (ECF).^[3] Cells may channel intracellular PP_i into ECF.^[4] ANK is a nonenzymatic plasma-membrane PP_i channel that supports extracellular PP_i levels.^[4] Defective function of the membrane PP_i channel ANK is associated with low extracellular PP_i and elevated intracellular PP_i.^[3] Ectonucleotide pyrophosphatase/phosphodiesterase (ENPP) may function to raise extracellular PP_i.^[4]

From the standpoint of high energy phosphate accounting, the hydrolysis of ATP to AMP and PP_i requires two high-energy phosphates, as to reconstitute AMP into ATP requires two phosphorylation reactions.

AMP + ATP → 2 ADP

2 ADP + 2 P_i → 2 ATP

References

^ C.Michael Hogan. 2011. Phosphate. Encyclopedia of Earth. Topic ed. Andy Jorgensen. Ed.-in-Chief C.J.Cleveland. National Council for Science and the Environment. Washington DC
^ Huebner PWA, Milburn RM (May 1980). "Hydrolysis of pyrophosphate to orthophosphate promoted by cobalt(III). Evidence for the role of polynuclear species". Inorg Chem. 19 (5): 1267–72. doi:10.1021/ic50207a032.
^ ^a ^b Ho AM, Johnson MD, Kingsley DM (Jul 2000). "Role of the mouse ank gene in control of tissue calcification and arthritis". Science. 289 (5477): 265–70. doi:10.1126/science.289.5477.265. PMID 10894769.
^ ^a ^b ^c Rutsch F, Vaingankar S, Johnson K, Goldfine I, Maddux B, Schauerte P, Kalhoff H, Sano K, Boisvert WA, Superti-Furga A, Terkeltaub R (Feb 2001). "PC-1 nucleoside triphosphate pyrophosphohydrolase deficiency in idiopathic infantile arterial calcification". Am J Pathol. 158 (2): 543–54. doi:10.1016/S0002-9440(10)63996-X. PMC 1850320. PMID 11159191.

External links

Look up diphosphate or pyrophosphate in Wiktionary, the free dictionary.

Pyrophosphates at the US National Library of Medicine Medical Subject Headings (MeSH)

UpToDate Contents

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English Journal

Identification of several hub-genes associated with periodontitis using integrated microarray analysis.

Guo X1, Wang Y2, Wang C1, Chen J3.
Molecular medicine reports.Mol Med Rep.2015 Apr;11(4):2541-7. doi: 10.3892/mmr.2014.3031. Epub 2014 Dec 2.
The aim of the present study was to identify differentially expressed genes and biological processes associated with periodontitis. In this study, the most significant 200 differentially expressed genes associated with periodontitis were identified using integrated analysis of multiple microarray da
PMID 25483140

Analysis of the protein-protein interaction networks of differentially expressed genes in pulmonary embolism.

Wang H1, Wang C1, Zhang L1, Lu Y1, Duan Q2, Gong Z2, Liang A3, Song H2, Wang L2.
Molecular medicine reports.Mol Med Rep.2015 Apr;11(4):2527-33. doi: 10.3892/mmr.2014.3006. Epub 2014 Nov 26.
The aim of the present study was to explore the function and interaction of differentially expressed genes (DEGs) in pulmonary embolism (PE). The gene expression profile GSE13535, was downloaded from the Gene Expression Omnibus database. The DEGs 2 and 18 h post‑PE initiation were identified us
PMID 25434468

Prenatal LPS-exposure--a neurodevelopmental rat model of schizophrenia--differentially affects cognitive functions, myelination and parvalbumin expression in male and female offspring.

Wischhof L1, Irrsack E2, Osorio C2, Koch M2.
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Maternal infection during pregnancy increases the risk for the offspring to develop schizophrenia. Gender differences can be seen in various features of the illness and sex steroid hormones (e.g. estrogen) have strongly been implicated in the disease pathology. In the present study, we evaluated sex
PMID 25455585

Japanese Journal

タンパク質ドメインの特徴を用いたカーネルマシンによるタンパク質間相互作用強度予測

鎌田真由美 ,佐久間裕介 ,林田守広 ,阿久津達也
情報処理学会研究報告. MPS, 数理モデル化と問題解決研究報告 2014-MPS-98(12), 1-6, 2014-06-18
… 間相互作用 (PPI) に関する実験研究や計算機による予測手法開発がこれまでに多く行われている.更に,PPI を相互作用するか・しないかの 2 値ではなく,多値として扱う為に導入された,PPI の強度という概念がある.この PPI 強度がタンパク質の特異性や機能性にも関連すると考えられている.そこで本研究では,アミノ酸配列から PPI 強度を予測 …
NAID 110009795490

タンパク質ドメインの特徴を用いたカーネルマシンによるタンパク質間相互作用強度予測

鎌田真由美 ,佐久間裕介 ,林田守広 ,阿久津達也
情報処理学会研究報告. BIO, バイオ情報学 2014-BIO-38(12), 1-6, 2014-06-18
… 間相互作用 (PPI) に関する実験研究や計算機による予測手法開発がこれまでに多く行われている.更に,PPI を相互作用するか・しないかの 2 値ではなく,多値として扱う為に導入された,PPI の強度という概念がある.この PPI 強度がタンパク質の特異性や機能性にも関連すると考えられている.そこで本研究では,アミノ酸配列から PPI 強度を予測 …
NAID 110009795447

H₂ブロッカー,PPI,防御因子増強薬 (特集外来で汎用される薬剤の上手な使い方) -- (各種薬剤の選び方と上手な使い方)

棚橋仁,村上和成
臨牀と研究 91(3), 348-354, 2014-03
NAID 40020021222

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リンク元	「ヒポキサンチン・グアニンホスホリボシルトランスフェラーゼ」「アデニンホスホリボシルトランスフェラーゼ」「ピロリン酸」「pyrophosphate」「無機ピロリン酸」
関連記事	「PPI」「PP」「P」

「ヒポキサンチン・グアニンホスホリボシルトランスフェラーゼ」

Pyrophosphate
	Other names Diphosphate or dipolyphosphate
Identifiers
PubChem	644102
ChemSpider	559142
DrugBank	DB04160
ChEBI	CHEBI:18361
Jmol-3D images	Image 1
	SMILES [O-]P(=O)([O-])OP(=O)([O-])[O-] ;
	InChI InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4 ; Key: XPPKVPWEQAFLFU-UHFFFAOYSA-J InChI=1/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4; Key: XPPKVPWEQAFLFU-XBHQNQODAI ;
Properties
Molecular formula	P2O74−
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references