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Phosphoramidates (sometimes also called amidophosphates) are a class of
Phosphoramidates (sometimes also called amidophosphates) are a class of phosphorus
Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Ear ...
compounds structurally related to phosphate
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 orthophosphoric acid .
The phosphate or orthophosphate ion is derived from phospho ...
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 a ...
s) via the substitution of an OR for a NR2. They are derivatives of phosphoramidic acids O=P(OH)(NR2)2, O=P(OH)2(NR2).
A phosphorodiamidate (or 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. DAP has attracted interest in the area of primordial chemis ...
) is a phosphate
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 orthophosphoric acid .
The phosphate or orthophosphate ion is derived from phospho ...
that has two of its OH groups substituted by NR2 groups to give a species with the general formula O=P(OH)(NH2)2.
The substitution of all three OH groups gives the phosphoric triamides (O=P(NR2)3), which are commonly referred to as phosphoramides
Phosphoramides are a class of phosphorus compounds with the formula O=P(NR2)3-n(OH)n. They can be considered derivatives of phosphoric acid where OH groups have been replaced with an amino or R-substituted amino group. In practise the term is com ...
.
Examples
Two examples of natural phosphoramidates arephosphocreatine
Phosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylated form of creatine that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle, myocardium and the brain to recycle adenosine tr ...
and the phosphoramidate formed when histidine residues in histidine kinase
Histidine kinases (HK) are multifunctional, and in non-animal kingdoms, typically transmembrane, proteins of the transferase class of enzymes that play a role in signal transduction across the cellular membrane. The vast majority of HKs are homod ...
s 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 the branch of biology that seeks to understand the molecular basis of biological activity in and between cells, including biomolecular synthesis, modification, mechanisms, and interactions. The study of chemical and physi ...
.
See also
*Phosphoramidite
A phosphoramidite (RO)2PNR2 is a monoamide of a phosphite diester. The key feature of phosphoramidites is their markedly high reactivity towards nucleophiles catalyzed by weak acids ''e.c''., triethylammonium chloride or 1''H''-tetrazole. In these ...
References