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Diamidophosphate (DAP) is the simplest
phosphorodiamidate In organophosphorus chemistry, phosphoramidates (sometimes also called amidophosphates) are a class of phosphorus compounds structurally related to phosphates (or organophosphates) via the substitution of an group for an amine group (). They ...
ion, with formula PO2(NH2)2−. It is a
phosphorylating In biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols: : This equation can be writt ...
ion and was first used for the phosphorylation of sugars in aqueous medium. DAP has attracted interest in the area of primordial chemistry.


Salts

Several salts of the formula MPO2(NH2)2(H2O)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 the ...
. 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 dithiophosphate salt KPO2(NH2)2 is also known. *Phosphorodiamidic acid crystallizes as a trihydrate.


Reactions

Heating anhydrous sodium diamidophosphate causes polymerization: *At 160 °C, Na2P2O4(NH)(NH2)2, Na3P3O6(NH)2(NH2)2, Na4P4O8(NH)3(NH2)2, Na5P5O10(NH)4(NH2)2 and Na6P6O12(NH)5(NH2)2 are produced. These substances contain P-N-P backbones. These can be separated by paper chromatography. *At 200 °C the hexa-phosphate is produced. *At 250 °C the typical chain length is 18. Heating hydrated salts induces the loss of ammonia to form oligophosphates and
polyphosphate A polyphosphate is a Salt (chemistry), salt or ester of polymeric oxyanions formed from tetrahedral PO4 (phosphate) structural units linked together by sharing oxygen atoms. Polyphosphates can adopt linear or a cyclic (also called, ring) structure ...
s. Diamidophosphate inhibits
urease Ureases (), functionally, belong to the superfamily of amidohydrolases and phosphotriesterases. Ureases are found in numerous Bacteria, Archaea, fungi, algae, plants, and some invertebrates. Ureases are nickel-containing metalloenzymes of high ...
enzymes by blocking up the active site, binding to two nickel centers. Diamidophosphate mimics the
urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...
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, Archaea, fungi, algae, plants, and some invertebrates. Ureases are nickel-containing metalloenzymes of high ...
, is a controlled release fertilizer. Numerous organic derivatives are known. One example is
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 the ...
.


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 Abiogenesis is the natural process by which life arises from non-living matter, such as simple organic compounds. The prevailing scientific hypothesis is that the transition from non-living to living entities on Earth was not a single even ...


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 Amines