Diamidophosphate (DAP) is the simplest
phosphorodiamidate ion, with formula PO
2(NH
2)
2−. It is a
phosphorylating ion and was first used for phosphorylation of sugars in aqueous medium. DAP has attracted interest in the area of primordial chemistry.
Salts
Several salts of the formula MPO
2(NH
2)
2(H
2O)
x are known.
[
*The sodium salt can be made by base hydrolysis of ]phenyl phosphorodiamidate
Phenyl phosphorodiamidate is an organophosphorus compound with the formula C6H5OP(O)(NH2)2. A white solid, it is used as an inhibitor of urease, an enzyme that accelerates the hydrolysis of urea. In this way, phenyl phosphorodiamidate enhances th ...
.[ It crystallises as a hexahydrate. It can be dehydrated.
*The silver salt AgPO2(NH2)2 can react using double decomposition with bromides forming other salts.
*The potassium diamidophosphate salt KPO2(NH2)2 is also known.
*Phosphorodiamidic acid crystallizes as a trihydrate.]
Reactions
Heating anhydrous sodium diamidophosphate causes polmerization:polyphosphate
Polyphosphates are salts or esters of polymeric oxyanions formed from tetrahedral PO4 (phosphate) structural units linked together by sharing oxygen atoms. Polyphosphates can adopt linear or a cyclic ring structures. In biology, the polyphosphate e ...
s.[
Diamidophosphate inhibits ]urease
Ureases (), functionally, belong to the superfamily of amidohydrolases and phosphotriesterases. Ureases are found in numerous bacteria, fungi, algae, plants, and some invertebrates, as well as in soils, as a soil enzyme. They are nickel-contai ...
enzymes by blocking up the active site, binding to two nickel centers. Diamidophosphate mimics the urea
Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid.
Urea serves an important ...
hydrolysis intermediate.
Diamidophosphate is tribasic, and the amine groups may also lose hydrogen to form more metallic salts. With silver, further reactions can yield explosive salts: tetrasilver orthodiamidophosphate (AgO)3P(NH2)NHAg, and pentasilver orthodiamidophosphate (AgO)3P(NHAg)2.
Organic esters and amides
left, Phenyl phosphorodiamidate, an inhibitor of urease
Ureases (), functionally, belong to the superfamily of amidohydrolases and phosphotriesterases. Ureases are found in numerous bacteria, fungi, algae, plants, and some invertebrates, as well as in soils, as a soil enzyme. They are nickel-contai ...
, is a controlled release fertilizers.phenyl phosphorodiamidate
Phenyl phosphorodiamidate is an organophosphorus compound with the formula C6H5OP(O)(NH2)2. A white solid, it is used as an inhibitor of urease, an enzyme that accelerates the hydrolysis of urea. In this way, phenyl phosphorodiamidate enhances th ...
.
Reactions with nucleosides
DAP phosphorylates deoxynucleosides (the building blocks of DNA, and at the same time initiates polymerization to make DNA. DAP facilitates the synthesis of larger RNA sequences (ribozymes) from smaller RNA strands. Other nitrogenous derivatives of phosphorus derivatives have also been proposed in this context in a review article.
See also
* Abiogenesis
In biology, abiogenesis (from a- 'not' + Greek bios 'life' + genesis 'origin') or the origin of life is the natural process by which life has arisen from non-living matter, such as simple organic compounds. The prevailing scientific hypothes ...
References
Other reading
*{{cite journal, last1=H. N. Stokes, title=On Diamidoorthophosphoric and Diamidotrihydroxyphosphoric Acids, journal=American Chemical Journal, date=1894, volume=16, issue=2, page=123
Phosphorus compounds
Amines
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