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]

Alafosfalin, a structural analogue of alanylalanine, is a medicinally important aminophosphonate.

Phosphonates are more difficult to hydrolyse than phosphates.[3]

Preparation

Aminophosphonates are often prepared by the condensation of imines and phosphorous acid (Pudovik reaction or Kabachnik–Fields reaction). More commonly the esters of phosphorous acid, e.g.diphenylphosphite, are employed. Because these compounds are of pharmaceutical interest, methods have been developed to induce these additions asymmetrically.[4]

References

  1. ↑ Pedro Merino; Eugenia Marqués-López; Raquel P. Herrera (2008). "Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines". Advanced Synthesis & Catalysis. 350: 1195–1208. doi:10.1002/adsc.200800131.
  2. ↑ Tušek-Božić, LJ (2013). "Aminophosphonate metal complexes of biomedical potential". Current Medicinal Chemistry. 20 (16): 2096–117. 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. PMID 20214568.
  4. ↑ Pedro Merino; Eugenia Marqués-López; Raquel P. Herrera (2008). "Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines". Advanced Synthesis & Catalysis. 350: 1195–1208. doi:10.1002/adsc.200800131.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.