Aminophosphonates are

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

s with the formula (RO)₂P(O)CR'₂NR"₂. These compounds are structural analogues of

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...

s in which a carboxylic moiety is replaced by phosphonic acid or related groups. Acting as antagonists of amino acids, they inhibit

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...

s involved in

amino acid metabolism Protein metabolism denotes the various biochemical processes responsible for the synthesis of proteins and amino acids (anabolism), and the breakdown of proteins by catabolism. The steps of protein synthesis include transcription, translation, and ...

and thus affect the physiological activity of the cell. These effects may be exerted as

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

, plant growth regulatory or

neuromodulatory Neuromodulation is the physiological process by which a given neuron uses one or more chemicals to regulate diverse populations of neurons. Neuromodulators typically bind to metabotropic, G-protein coupled receptors (GPCRs) to initiate a second ...

. They can act as ligands, and heavy metal complexes with aminophosphonates have had medical applications investigated. Phosphonates are more difficult to hydrolyse than phosphates.

Preparation

Aminophosphonates are often prepared by hydrophosphonylation, usually the condensation of

imine In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bo ...

s and

phosphorous acid Phosphorous acid (or phosphonic acid (singular)) is the compound described by the formula H3PO3. This acid is diprotic (readily ionizes two protons), not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in th ...

. In the

Pudovik reaction In organophosphorus chemistry, the Pudovik reaction is a method for preparing α-aminomethylphosphonates. Under basic conditions, the phosphorus–hydrogen bond of a dialkylphosphite, (RO)2P(O)H, adds across the carbon–nitrogen double b ...

Kabachnik–Fields reaction In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming aminophosphonate, α-aminomethylphosphonates from an amine, a carbonyl compound, and a phosphite ester, dialkyl phosphonate, (RO)2P(O)H (tha ...

the esters of phosphorous acid are employed, e.g. diphenylphosphite. Because these compounds are of pharmaceutical interest, methods have been developed to induce these additions asymmetrically.

Examples

Aminomethylphosphonic_acid.svg,

Aminomethylphosphonic acid Aminomethylphosphonic acid (AMPA) is a weak organic acid with a phosphonic acid group. Application AMPA apparently can be used as biocide and pesticide. AMPA is also used in research to assess the exposure of glyphosate. Environmental fate ...

, the simplest possible aminophosphonate. Glyphosate.svg,

Glyphosate Glyphosate (IUPAC name: ''N''-(phosphonomethyl)glycine) is a broad-spectrum Herbicide, systemic herbicide and Crop desiccation, crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plan ...

, a common though contentious herbicide EDTMP.png,

EDTMP EDTMP or ethylenediamine tetra(methylene phosphonic acid) is a phosphonic acid. It has chelate, chelating and anti corrosion properties. EDTMP is the phosphonate analog of EDTA.Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic, ...

, a

chelating Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a Denticity, polydentate (multiple bonded) ligand and a single central metal atom. These l ...

agent. Its ¹⁵³Sm complex (

Quadramet Samarium (153Sm) lexidronam (chemical name Samarium-153-ethylene diamine tetramethylene phosphonate, abbreviated Samarium-153 EDTMP, trade name Quadramet) is a chelated complex of a radioisotope of the element samarium with EDTMP. It is used t ...

) is used in the treatment of cancer

References

{{Reflist Amino acids Phosphonic acids