Diamidophosphate

Diamidophosphate (DAP) is the simplest phosphorodiamidate ion, with formula PO2(NH2)2−. It is a phosphorylating ion and was first used for phosphorylation of sugars in aqueous medium.[1] Diamidophosphate can form salts such as sodium diamidophosphate, or an acid phosphorodiamidic acid. Phosphorodiamidic acid can crystallize as a trihydrate.[2] It is hypothesized as a plausible primordial reagent in the emergence of the first peptides, cell membrane lipids and nucleotides, the precursors of all life on Earth.[3] In a November 6, 2017 press release from the Scripps Research Institute, DAP was described as "a compound that may have been a crucial factor in the origins of life on Earth".[4] Other nitrogenous derivatives of phosphorus derivatives have also been proposed in this context in a review article.[5]

Diamidophosphate
Names
IUPAC name
diaminophosphinate
Identifiers
3D model (JSmol)
ChemSpider
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).
Infobox references

Production

Diamidophosphate compounds can be made from phenyl diamidophosphate (phenylphosphorodiamidate) reacting with sodium hydroxide in a water solution. This solution can crystallise sodium diamidophosphate. Phosphorodiamidic acid trihydrate can be precipitated from the solution by adding it to an excess of ethanol.[2]

Reactions

The sodium salt crystallises as a hexahydrate. It can be dehydrated by heating at 70°C for a week.[6]

When anhydrous sodium diamidophosphate is heated it polmerises. 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 a P-N-P backbone. These can be separated by paper chromatography.[6] At 200°C heat the hexa-phosphate is the most common and at 250°C the typical chain length is 18.[6] If hydrated salts are strongly heated they lose ammonia to form oligophosphates and polyphosphates.[6] This compares with the heating of sodium amidophosphate, which yields sodium imidodiphosphate Na4P2O6NH and sodium nitridotriphosphate Na6P3O9N is produced also.[6]

Diamidophosphate binds to nickel ions, and inhibits urease enzymes by blocking up the active site, binding to two nickel atoms. Diamidophosphate mimics the urea hydrolysis intermediate.[7]

A silver AgPO2(NH2)2 and a potassium diamidophosphate salt KPO2(NH2)2 are also known. The silver salt can react using double decomposition with bromides forming other salts.[6]

Diamidophosphate can also be 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.[8]

Numerous organic derivatives are known. Organic groups can substitute on the oxygen for the OH group, or replace a hydrogen on the amine group.[9]

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gollark: Python is slow and provides few static guarantees and has awful dependency management. Rust is too dependencyuous and often inflexible. Nim has basically no libraries or popular support. All other programming languages are dominated options, as far as I know, by my arbitrary standards.

References
  1. Krishnamurthy, Ramanarayanan; Guntha, Sreenivasulu; Eschenmoser, Albert (4 July 2000). "Regioselective α-Phosphorylation of Aldoses in Aqueous Solution". Angewandte Chemie International Edition. 39 (13): 2281–2285. doi:10.1002/1521-3773(20000703)39:13<2281::AID-ANIE2281>3.0.CO;2-2. ISSN 1521-3773. PMID 10941064.
  2. Coggins, Adam J.; Powner, Matthew W. (10 October 2016). "Prebiotic synthesis of phosphoenol pyruvate by α-phosphorylation-controlled triose glycolysis Supplementary Information Compound 8" (PDF). Nature Chemistry. 9 (4): 310–317. Bibcode:2017NatCh...9..310C. doi:10.1038/nchem.2624. ISSN 1755-4349. PMID 28338685.
  3. "Phosphorylation, Oligomerization and Self-assembly in Water Under Potential Prebiotic Conditions", Gibard et al, Nature Chemistry (2017) doi:10.1038/nchem.2878, published online 06 November 2017
  4. "Scientists Find Potential "Missing Link" in Chemistry That Led to Life on Earth". Scripps Research Institute. November 6, 2017. Retrieved 7 November 2017.
  5. Karki, Megha; Gibard, Clémentine; Bhowmik, Subhendu; Krishnamurthy, Ramanarayanan (2017-07-29). "Nitrogenous Derivatives of Phosphorus and the Origins of Life: Plausible Prebiotic Phosphorylating Agents in Water". Life. 7 (3): 32. doi:10.3390/life7030032. PMC 5617957. PMID 28758921.
  6. Klement, R.; Biberacher, G. (May 1956). "Das thermische Verhalten von Natriumdiamidophosphat, Darstellung von kondensierten Imidophosphaten". Zeitschrift für Anorganische und Allgemeine Chemie. 285 (1–2): 74–85. doi:10.1002/zaac.19562850109.
  7. Zamble, Deborah; Rowińska-Żyrek, Magdalena; Kozlowski, Henryk (2017). The Biological Chemistry of Nickel. Royal Society of Chemistry. pp. 73–74, 83. ISBN 9781788010580.
  8. Bretherick, L. (2016). Bretherick's Handbook of Reactive Chemical Hazards. Elsevier. p. 19. ISBN 9781483162508.
  9. Kiss, S.; Simihaian, M. (2013). Improving Efficiency of Urea Fertilizers by Inhibition of Soil Urease Activity. Springer Science & Business Media. pp. 105–108. ISBN 9789401718431.

See also

Other reading
  • H. N. Stokes (1894). "On Diamidoorthophosphoric and Diamidotrihydroxyphosphoric Acids". American Chemical Journal. 16 (2): 123.
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