Aminophosphonate

Aminophosphonates are organophosphorus compounds with the formula (RO)2P(O)CR'2NR"2. These compounds are structural analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups.[1] Acting as antagonists of amino acids, they inhibit enzymes involved in amino acid metabolism and thus affect the physiological activity of the cell. These effects may be exerted as antibacterial, plant growth regulatory or neuromodulatory. They can act as ligands, and heavy metal complexes with aminophosphonates have had medical applications investigated.[2]

Phosphonates are more difficult to hydrolyse than phosphates.[3] Some aminophosphonates degrade to AMPA.[4]

  1. ^ Pedro Merino; Eugenia Marqués-López; Raquel P. Herrera (2008). "Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines". Advanced Synthesis & Catalysis. 350 (9): 1195–1208. doi:10.1002/adsc.200800131. hdl:10261/114023.
  2. ^ Tušek-Božić, LJ (2013). "Aminophosphonate metal complexes of biomedical potential". Current Medicinal Chemistry. 20 (16): 2096–117. doi:10.2174/0929867311320160004. PMID 23432587.
  3. ^ Orsini, F; Sello, G; Sisti, M (2010). "Aminophosphonic acids and derivatives. Synthesis and biological applications". Current Medicinal Chemistry. 17 (3): 264–89. doi:10.2174/092986710790149729. PMID 20214568.
  4. ^ Schwientek, M.; Rügner, H.; Haderlein, S.B.; Schulz, W.; Wimmer, B.; Engelbart, L.; Bieger, S.; Huhn, C. (2024). "Glyphosate contamination in European rivers not from herbicide application?". Water Research. 263: 122140. doi:10.1016/j.watres.2024.122140.