Aminophosphonates are

organophosphorus compound Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...

s with the formula (RO)₂P(O)CH₂NR₂. These compounds are structural analogues of

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...

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

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

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 secon ...

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

aminomethylphosphonic acid Aminomethylphosphonic acid (AMPA) is a aminophosphonate with a weak 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 f ...

Preparation

Aminophosphonates are often prepared by

hydrophosphonylation In chemistry hydrophosphonylation refers to any reaction where addition across a double bond generates a phosphonate (RP(O)(OR')2) group. Examples include the Kabachnik–Fields reaction, where a dialkylphosphite reacts across an imine to form an am ...

, 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 bon ...

s and

phosphorous acid Phosphorous acid (or phosphonic acid) is the Compound (chemistry), compound described by the chemical formula, formula . It is diprotic (readily ionizes two protons), not triprotic as might be suggested by its formula. Phosphorous acid is an in ...

. 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 ...

Kabachnik–Fields reaction In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming α-aminomethylphosphonates from an amine, a carbonyl compound, and a dialkyl phosphonate, (RO)2P(O)H (that are also called dialkylphosphi ...

, 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 aminophosphonate with a weak 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 f ...

(AMPA), 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 EPSP inhibitor, inhibiting the plant enzyme 5-en ...

, a common though contentious herbicide ATMP.png,

ATMP ATMP or aminotris(methylenephosphonic acid) is a phosphonic acid with chemical formula N(CH2PO3H2)3. It is a colorless solid. Its conjugate bases, such as (CH2PO3H)3sup>3-, have chelating properties. ATMP can be synthesized from the Mannich- ...

is used in

water treatment Water treatment is any process that improves the quality of water to make it appropriate for a specific end-use. The end use may be drinking, industrial water supply, irrigation, river flow maintenance, water recreation or many other uses, ...

antiscalant An antiscalant is a chemical or pre-treatment chemical that prevents the formation of scale, or crystallized mineral salts, commonly used in water purification systems, pipelines and cooling tower applications. Antiscalants are also known as scale ...

EDTMP.png,

EDTMP EDTMP or ethylenediamine tetra(methylene phosphonic acid) is a phosphonic acid. It has chelating and anti corrosion properties. EDTMP is the phosphonate analog of EDTA.Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic," In 'Ul ...

, a

chelating Chelation () is a type of bonding of ions and their 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 l ...

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

References

{{Reflist Amino acids Phosphonic acids Phosphonates Chelating agents