Pyrophosphate

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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 PP_i and is formed by the hydrolysis of ATP into AMP in cells.

• ATP + H₂O <=> 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 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:

• P₂O₇⁴⁻ + H₂O → 2 HPO₄²⁻

or in shorthand notation:

• PP_i + H₂O → 2 P_i

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

This hydrolysis to inorganic phosphate effectively renders the cleavage of ATP to AMP and PP_i 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.

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

• AMP + ATP → 2 ADP
• 2 ADP + 2 P_i → 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.

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
• 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
• Chondrocalcinosis
• Hypercalcemia
• Lesch-Nyhan's syndrome
• Periodontitis
• Water on the knee

• Foscarnet

• Phosphate homeostasis
• Phosphorus oxoacids
• Pyrosequencing
• Structural phosphate

External links

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