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 ...

s in which a

carboxylic moiety In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with substituent, R referring to the alkyl, alkenyl, aryl, or other group. ...

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 substrate (chemistry), substrates, and the enzyme converts the substrates into different molecule ...

s involved in amino acid metabolism 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 ...

, 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 the ...

. In the Pudovik reaction or Kabachnik–Fields reaction 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, the simplest possible aminophosphonate. Glyphosate.svg,

Glyphosate Glyphosate (IUPAC name: ''N''-(phosphonomethyl)glycine) is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshik ...

, a common though contentious herbicide EDTMP.png, EDTMP, 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 polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...

agent. Its ¹⁵³Sm complex ( Quadramet) is used in the treatment of cancer

References

{{Reflist Amino acids Phosphonic acids