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词条 Aminophosphonate
释义

  1. Preparation

  2. References

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]

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. ^{{cite journal|volume=350|year=2008|pages=1195–1208|title=Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines|author=Pedro Merino|author2=Eugenia Marqués-López|author3=Raquel P. Herrera|journal=Advanced Synthesis & Catalysis|doi=10.1002/adsc.200800131}}
2. ^{{cite journal|last1=Tušek-Božić|first1=LJ|title=Aminophosphonate metal complexes of biomedical potential.|journal=Current Medicinal Chemistry|date=2013|volume=20|issue=16|pages=2096–117|pmid=23432587}}
3. ^{{cite journal|last1=Orsini|first1=F|last2=Sello|first2=G|last3=Sisti|first3=M|title=Aminophosphonic acids and derivatives. Synthesis and biological applications.|journal=Current Medicinal Chemistry|date=2010|volume=17|issue=3|pages=264–89|pmid=20214568}}
4. ^{{cite journal|volume=350|year=2008|pages=1195–1208|title=Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines|author=Pedro Merino|author2=Eugenia Marqués-López|author3=Raquel P. Herrera|journal=Advanced Synthesis & Catalysis|doi=10.1002/adsc.200800131}}

2 : Amino acids|Phosphonic acids

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