Pyridoxal-Mediated Dephosphonylation of 1-Amino Phosphonic Acids

Article abstract of DOI:10.1021/jo00392a029

The reaction between pyridoxal and α-amino phosphonic acids is reported.Under the proper conditions, the amino phosphonates can be induced to undergo a pyridoxal-promoted cleavage of the P-C bond.The reaction requires a metal ion and a phosphonic acid that possesses a chelating heteroatom in a position β to the amino group.At 100 deg C and pH 8.8, the dephosphonylation reaction is a first-order process, producing orthophosphate and an aldehyde from the amino phosphonate and pyridoxamine from the pyridoxal.The mechanism proposed for this reaction is based on an analogy with the pyridoxal-catalyzed decarboxylation of α-amino acids.The reactions reported represent the first observation of an α dephosphonylation mediated by pyridoxal.