Pyrophosphate: Difference between revisions

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{{SI}}
{{SI}}
'''Editor-In-Chief:''' Henry A. Hoff
'''Editor-In-Chief:''' Henry A. Hoff
[[Image:Pyrophosphate-3D-balls.png|thumb|right|250px|[[Ball-and-stick model]] of the pyrophosphate anion, P<sub>2</sub>O<sub>7</sub><sup>4−</sup>]]
[[Image:Pyrophosphate-3D-balls.png|thumb|right|250px|[[Ball-and-stick model]] of the pyrophosphate anion, P<sub>2</sub>O<sub>7</sub><sup>4−</sup>]]


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For example, when a nucleotide is incorporated into a growing [[DNA]] or [[RNA]] strand by a [[polymerase]], pyrophosphate (PP<sub>i</sub>) is released. Pyrophosphorolysis is the reverse of the [[polymerization]] reaction where 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).
For example, when a nucleotide is incorporated into a growing [[DNA]] or [[RNA]] strand by a [[polymerase]], pyrophosphate (PP<sub>i</sub>) is released. Pyrophosphorolysis is the reverse of the [[polymerization]] reaction where 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 P<sub>2</sub>O<sub>7</sub><sup>4&minus;</sup>, and is an [[acid]] [[anhydride]] of [[phosphate]]. It is unstable in [[aqueous solution]] and in the absence of enzymic catalysis [[hydrolysis|hydrolyze]]s extremely slowly into inorganic phosphate in all but highly acidic media:<ref name=Huebner>{{ cite journal |author=Huebner PWA, Milburn RM |title=Hydrolysis of pyrophosphate to orthophosphate promoted by cobalt(III). Evidence for the role of polynuclear species |journal=Inorg Chem. |year=1980 |volume=19 |issue=5 |pages=1267-72 |month=May |pmid= |doi=10.1021/ic50207a032 }}</ref>
The pyrophosphate anion has the structure P<sub>2</sub>O<sub>7</sub><sup>4&minus;</sup>, and is an [[acid]] [[anhydride]] of [[phosphate]]. It is unstable in [[aqueous solution]] and in the absence of enzymic catalysis [[hydrolysis|hydrolyze]]s extremely slowly into inorganic phosphate in all but highly acidic media:<ref name=Huebner>{{ cite journal |author=Huebner PWA, Milburn RM |title=Hydrolysis of pyrophosphate to orthophosphate promoted by cobalt(III). Evidence for the role of polynuclear species |journal=Inorg Chem.
|volume=19 |issue=5 |pages=1267-72 |date=May 1980|pmid= |doi=10.1021/ic50207a032 }}</ref>


* P<sub>2</sub>O<sub>7</sub><sup>4−</sup> + H<sub>2</sub>O → 2 HPO<sub>4</sub><sup>2&minus;</sup>
* P<sub>2</sub>O<sub>7</sub><sup>4−</sup> + H<sub>2</sub>O → 2 HPO<sub>4</sub><sup>2&minus;</sup>
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Enzyme EC 3.6.1.1 catalyzes this hydrolysis.<ref name=3.6.1.1>{{ cite web |title=NiceZyme View of ENZYME: EC 3.6.1.1 |url=http://www.expasy.org/enzyme/3.6.1.1 }}</ref> Specificity varies with the source and with the activating metal ion, e.g. Mg<sup>2+</sup>.<ref name=3.6.1.1/>
Enzyme EC 3.6.1.1 catalyzes this hydrolysis.<ref name=3.6.1.1>{{ cite web |title=NiceZyme View of ENZYME: EC 3.6.1.1 |url=http://www.expasy.org/enzyme/3.6.1.1 }}</ref> Specificity varies with the source and with the activating metal ion, e.g. Mg<sup>2+</sup>.<ref name=3.6.1.1/>
Human GeneID: 5464
[[PPA1]]; pyrophosphatase (inorganic) 1 (EC: 3.6.1.1); K01507 inorganic pyrophosphatase [EC: 3.6.1.1]
Human GeneID: 27068
[[PPA2]]; pyrophosphatase (inorganic) 2 (EC:3.6.1.1); K01507 inorganic pyrophosphatase [EC: 3.6.1.1]
Human GeneID: 64077
[[LHPP]]; phospholysine phosphohistidine inorganic pyrophosphate phosphatase (EC: 3.6.1.1); K11725 phospholysine phosphohistidine inorganic pyrophosphate phosphatase [EC: 3.6.1.1, EC: 3.1.3.-]
Human GeneID: 89797
[[NAV2]]; neuron navigator 2 (EC: 3.6.1.1).


This hydrolysis to inorganic phosphate effectively renders the cleavage of ATP to AMP and PP<sub>i</sub> ultimately [[hydrolysis|irreversible]], and biochemical reactions coupled to this hydrolysis are irreversible as well, unless EC 3.6.1.1 is present. EC 3.6.1.1 can reverse the hydrolysis.<ref name=3.6.1.1/>
This hydrolysis to inorganic phosphate effectively renders the cleavage of ATP to AMP and PP<sub>i</sub> ultimately [[hydrolysis|irreversible]], and biochemical reactions coupled to this hydrolysis are irreversible as well, unless EC 3.6.1.1 is present. EC 3.6.1.1 can reverse the hydrolysis.<ref name=3.6.1.1/>
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== See also ==
== See also ==


* [[Phosphoric acids and phosphates]]
* [[Pyrophosphoric acid]]
* [[5-Diphosphomevalonic acid]]
* [[Adenosine diphosphate]] (ADP)
* [[Calcium pyrophosphate]]
* [[Cytidine diphosphate]]
* [[Dimethylallyl pyrophosphate]] (DMAPP)
* [[Disodium pyrophosphate]]
* [[(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate]]
* [[Farnesyl pyrophosphate]]
* [[Geranyl pyrophosphate]] (GPP)
* [[Geranylgeranyl pyrophosphate]]
* [[Guanosine diphosphate]] (GDP)
* [[High energy phosphate]]
* [[Isopentenyl pyrophosphate]] (IPP)
* [[Phosphoribosyl pyrophosphate]] (PRPP)
* [[Sodium pyrophosphate]]
* [[Sodium pyrophosphate]]
* [[Thiamine pyrophosphate]] (TPP)
* [[Thymidine diphosphate]] (TDP)
* [[Tricalcium phosphate]]
* [[Uridine diphosphate]] (UDP)
* [[Zinc pyrophosphate]]
* [[Acetate kinase (diphosphate)]]
* [[Amidophosphoribosyltransferase]]
* [[Diphosphate-glycerol phosphotransferase]]
* [[Diphosphate-purine nucleoside kinase]]
* [[Diphosphate-serine phosphotransferase]]
* [[Diphosphotransferase]]
* [[Dolichyldiphosphatase]]
* [[Ectonucleotide pyrophosphatase/phosphodiesterase 1]]
* [[Farnesyl-diphosphate farnesyltransferase]]
* [[Farnesyl-diphosphate kinase]]
* [[Inorganic diphosphatase]]
* [[Inorganic pyrophosphatase]]
* [[Isopentenyl-diphosphate delta isomerase]]
* [[Isopentenyl-diphosphate Delta-isomerase]]
* [[Monoterpenyl-diphosphatase]]
* [[Nucleoside-diphosphatase]]
* [[Prenyl-diphosphatase]]
* [[Pyrophosphate dependent phosphofructokinase]]
* [[Pyrophosphomevalonate decarboxylase]]
* [[RNA polymerase]]
* [[Thiamine pyrophosphatase]]
* [[Thiamine pyrophosphokinase]]
* [[Thiamine-diphosphate kinase]]
* [[2-amino-4-hydroxy-6-hydroxymethyldihydropteridine diphosphokinase]]
* [[Mevalonate pathway]]
* [[Non-mevalonate pathway]]
* [[Terpene]]
* [[Terpenoid]]
* [[Arthritis]]
* [[Arthropathy]]
* [[Calcium pyrophosphate dihydrate deposition disease]]
* [[Calcium pyrophosphate dihydrate deposition disease]]
* [[Chondrocalcinosis]]
* [[Hypercalcemia]]
* [[Lesch-Nyhan's syndrome]]
* [[Periodontitis]]
* [[Water on the knee]]
* [[Foscarnet]]
* [[Phosphate homeostasis]]
* [[Phosphorus oxoacids]]
* [[Pyrosequencing]]
* [[Structural phosphate]]


==External links==
==External links==
* {{MeshName|Pyrophosphates}}
* {{MeshName|Pyrophosphates}}
{{Phosphate biochemistry}}


[[Category:Phosphates]]
[[Category:Phosphates]]

Latest revision as of 01:10, 17 February 2020

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Editor-In-Chief: Henry A. Hoff

File:Pyrophosphate-3D-balls.png
Ball-and-stick model of the pyrophosphate anion, P2O74−

In chemistry, the anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The anion P2O74− is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells.

  • ATP + H2O <=> AMP + PPi

For example, when a nucleotide is incorporated into a growing DNA or RNA strand by a polymerase, pyrophosphate (PPi) is released. Pyrophosphorolysis is the reverse of the polymerization reaction where 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 in the absence of enzymic catalysis hydrolyzes extremely slowly into inorganic phosphate in all but highly acidic media:[1]

  • P2O74− + H2O → 2 HPO42−

or in shorthand notation:

  • PPi + H2O → 2 Pi

Enzyme EC 3.6.1.1 catalyzes this hydrolysis.[2] Specificity varies with the source and with the activating metal ion, e.g. Mg2+.[2]

Human GeneID: 5464 PPA1; pyrophosphatase (inorganic) 1 (EC: 3.6.1.1); K01507 inorganic pyrophosphatase [EC: 3.6.1.1]

Human GeneID: 27068 PPA2; pyrophosphatase (inorganic) 2 (EC:3.6.1.1); K01507 inorganic pyrophosphatase [EC: 3.6.1.1]

Human GeneID: 64077 LHPP; phospholysine phosphohistidine inorganic pyrophosphate phosphatase (EC: 3.6.1.1); K11725 phospholysine phosphohistidine inorganic pyrophosphate phosphatase [EC: 3.6.1.1, EC: 3.1.3.-]

Human GeneID: 89797 NAV2; neuron navigator 2 (EC: 3.6.1.1).

This hydrolysis to inorganic phosphate effectively renders the cleavage of ATP to AMP and PPi ultimately irreversible, and biochemical reactions coupled to this hydrolysis are irreversible as well, unless EC 3.6.1.1 is present. EC 3.6.1.1 can reverse the hydrolysis.[2]

From the standpoint of high energy phosphate accounting, the hydrolysis of ATP to AMP and PPi will require two high energy phosphates, as to reconstitute AMP into ATP will require two phosphorylation reactions.

  • AMP + ATP → 2 ADP
  • 2 ADP + 2 Pi → 2 ATP

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

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.

References

  1. ↑ 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.
  2. ↑ 2.0 2.1 2.2 "NiceZyme View of ENZYME: EC 3.6.1.1".

See also

External links

de:Diphosphate

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