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Diamidophosphate

Chemical compound From Wikipedia, the free encyclopedia

Diamidophosphate

Diamidophosphate (DAP) is the simplest phosphorodiamidate ion, with formula PO2(NH2)2−. It is a phosphorylating ion and was first used for the phosphorylation of sugars in aqueous medium.[1] DAP has attracted interest in the area of primordial chemistry.[2]

Quick Facts Names, Identifiers ...
Diamidophosphate
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Names
IUPAC name
diaminophosphinate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI==1S/H5N2O2P/c1-5(2,3)4/h(H5,1,2,3,4)/p-1
    Key: ANCLJVISBRWUTR-UHFFFAOYSA-M
  • NP(=O)(N)[O-]
Properties
H4N2O2P
Molar mass 95.018 g·mol−1
Related compounds
Other anions
 Thiophosphordiamidic acid
Other cations
 Phosphordiamidic acid
Related
phosphorotriamide
phosphoramidic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Salts

Several salts of the formula MPO2(NH2)2(H2O)x are known.[3]

  • The sodium salt can be made by base hydrolysis of phenyl phosphorodiamidate.[4] 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.[4]

Reactions

Summarize
Perspective

Heating anhydrous sodium diamidophosphate causes polymerization:[3]

  • 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 polyphosphates.[3]

Diamidophosphate inhibits urease enzymes by blocking up the active site, binding to two nickel centers. Diamidophosphate mimics the urea hydrolysis intermediate.[5]

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.[6]

Organic esters and amides

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Phenyl phosphorodiamidate, an inhibitor of urease, is a controlled release fertilizer.[7]

Numerous organic derivatives are known. One example is phenyl phosphorodiamidate.[8]

Reactions with nucleosides

DAP phosphorylates deoxynucleosides (the building blocks of DNA, and at the same time initiates polymerization to make DNA.[9] DAP facilitates the synthesis of larger RNA sequences (ribozymes) from smaller RNA strands.[10] Other nitrogenous derivatives of phosphorus derivatives have also been proposed in this context in a review article.[11]

See also

References

Other reading

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