In chemistry, pyrophosphates are phosphorus oxyanions that contain two phosphorus atoms in a P-O-P linkage. A number of pyrophosphate salts exist, such as disodium pyrophosphate (Na2H2P2O7) and tetrasodium pyrophosphate (Na4P2O7), among others. Often pyrophosphates are called diphosphates. The parent pyrophosphates are derived from partial or complete neutralization of pyrophosphoric acid. The pyrophosphate bond is also sometimes referred to as a phosphoanhydride bond, a naming convention which emphasizes the loss of water that occurs when two phosphates form a new P-O-P bond, and which mirrors the nomenclature for anhydrides of carboxylic acids. Pyrophosphates are found in ATP and other nucleotide triphosphates, which are very important in biochemistry.
Diphosphate or dipolyphosphate
3D model (JSmol)
|E number||E450 (thickeners, ...)|
|Molar mass||173.943 g·mol−1|
|Conjugate acid||Pyrophosphoric acid|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(what is ?)|
Pyrophosphates are prepared by heating phosphates, hence the name pyro-phosphate (from the Ancient Greek: πῦρ, πυρός, romanized: pyr, pyros, lit. 'fire'). More precisely, they are generated by heating phosphoric acids to the extent that a condensation reaction occurs.
Pyrophosphates are generally white or colorless. The alkali metal salts are water-soluble. 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.
- ATP → 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 in which pyrophosphate reacts with the 3′-nucleosidemonophosphate (NMP or dNMP), which is removed from the oligonucleotide to release the corresponding triphosphate (dNTP from DNA, or NTP from RNA).
7 + H2O → 2 HPO2−
or in biologists' shorthand notation:
- PPi + H2O → 2 Pi + 2 H+
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.
(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 PPi irreversible, and biochemical reactions coupled to this hydrolysis are irreversible as well.
PPi 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). Cells may channel intracellular PPi into ECF. ANK is a nonenzymatic plasma-membrane PPi channel that supports extracellular PPi levels. Defective function of the membrane PPi channel ANK is associated with low extracellular PPi and elevated intracellular PPi. Ectonucleotide pyrophosphatase/phosphodiesterase (ENPP) may function to raise extracellular PPi.
From the standpoint of high energy phosphate accounting, the hydrolysis of ATP to AMP and PPi requires two high-energy phosphates, as to reconstitute AMP into ATP requires two phosphorylation reactions.
- AMP + ATP → 2 ADP
- 2 ADP + 2 Pi → 2 ATP
The plasma concentration of inorganic pyrophosphate has a reference range of 0.58–3.78 µM (95% prediction interval).
Isopentenyl pyrophosphate converts to geranyl pyrophosphate the precursor to tens of thousand of terpenes and terpenoids.
As a food additive
Various diphosphates are used as emulsifiers, stabilisers, acidity regulators, raising agents, sequestrants, and water retention agents in food processing. They are classified in the E number scheme under E450:
- E450(a): disodium dihydrogen diphosphate; trisodium diphosphate; tetrasodium diphosphate (TSPP); tetrapotassium diphosphate
- E450(b): pentasodium and pentapotassium triphosphate
- E450(c): sodium and potassium polyphosphates
In particular, various formulations of diphosphates are used to stabilize whipped cream.
- Adenosine monophosphate
- Adenosine diphosphate
- Adenosine triphosphate
- ATP hydrolysis
- ATP synthase
- Calcium pyrophosphate
- Calcium pyrophosphate dihydrate deposition disease
- High energy phosphate
- Inorganic pyrophosphatase
- Nucleoside triphosphate
- Oxidative phosphorylation
- Phosphoric acid
- Phosphoric acids and phosphates
- Sodium pyrophosphate
- Thiamine pyrophosphate
- Zinc pyrophosphate
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