Phosphorodiamidate on:
[Wikipedia]
[Google]
[Amazon]
In organophosphorus chemistry, phosphoramidates (sometimes also called amidophosphates) are a class of
In organophosphorus chemistry, phosphoramidates (sometimes also called amidophosphates) are a class of phosphorus
Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared ar ...
compounds structurally related to phosphate
Phosphates are the naturally occurring form of the element phosphorus.
In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...
s (or organophosphate
In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered ...
s) via the substitution of an group for an amine group (). They are derivatives of phosphoramidic acids, which possess the structure or .
A phosphorodiamidate is a phosphate that has two of its hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
() groups substituted by amine () groups to give a species with the general formula . The substitution of all three OH groups gives the phosphoric triamides (), which are commonly referred to as phosphoramides.
Synthesis
In the Stokes method, phosphoramidates are synthesized fromphosphorus oxychloride
Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phos ...
. The compound reacts with phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
to form a chlorophosphonate
In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing Functional group, groups, where R is an organic group (alkyl, aryl). If R is hydrogen then the compound is a Phosphite_ester#Chemistry_of_HP(O)(OR ...
ester or diester, depending on stoichiometry
Stoichiometry () is the relationships between the masses of reactants and Product (chemistry), products before, during, and following chemical reactions.
Stoichiometry is based on the law of conservation of mass; the total mass of reactants must ...
. The remaining chlorine substituents then react with an amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
compound to give the phosphoramidate.
Examples
Two examples of natural phosphoramidates arephosphocreatine
Phosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylation, phosphorylated form of creatine that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle, myocardium and the brain to recyc ...
and the phosphoramidate formed when histidine residues in histidine kinases are phosphorylated.
An example of a phosphorodiamidate is morpholino
A Morpholino, also known as a Morpholino oligomer and as a phosphorodiamidate Morpholino oligomer (PMO), is a type of oligomer molecule (colloquially, an oligo) used in molecular biology to modify gene expression. Its molecular structure contains ...
which is used in molecular biology
Molecular biology is a branch of biology that seeks to understand the molecule, molecular basis of biological activity in and between Cell (biology), cells, including biomolecule, biomolecular synthesis, modification, mechanisms, and interactio ...
.
See also
* PhosphoramiditeReferences