Phosphoramidate
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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 Template:Chem2 group for an amine group (Template:Chem2). They are derivatives of phosphoramidic acids, which possess the structure Template:Chem2 or Template:Chem2.
A phosphorodiamidate is a phosphate that has two of its hydroxyl (Template:Chem2) groups substituted by amine (Template:Chem2) groups to give a species with the general formula Template:Chem2. The substitution of all three OH groups gives the phosphoric triamides (Template:Chem2), which are commonly referred to as phosphoramides.[1]
Synthesis
In the Stokes method, phosphoramidates are synthesized from phosphorus oxychloride. The compound reacts with phenol to form a chlorophosphonate ester or diester, depending on stoichiometry. The remaining chlorine substituents then react with an amine compound to give the phosphoramidate.[2]
Examples
Two examples of natural phosphoramidates are phosphocreatine and the phosphoramidate formed when histidine residues in histidine kinases are phosphorylated.[3] An example of a phosphorodiamidate is morpholino which is used in molecular biology.
See also
References
- ↑ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "phosphoramides". Script error: No such module "CS1 identifiers".Script error: No such module "TemplatePar".
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