2-aminoethylphosphonate, degradation

The phosphonatase (hydrolase) pathway is less widely used, typically for the degradation of 2-aminoethylphosphonate via phosphonoacetaldehyde to acetaldehyde, and the degradation of phosphonoacetate that involves a specific hydrolase (Kulakova et al. 2001). 

La Nauze JM, H Rosenberg (1968) The identification of 2-phosphonoacetaldehyde as an intermediate in the degradation of 2-aminoethylphosphonate by Bacillus cereus. Biochim Biophys Acta 165 438-447. 

The Hofmann degradation is applicable to the synthesis of 2-aminoalkylphosphonic acids." " For example, 2-aminoethylphosphonic acid has been obtained by this method in 75% yield (Scheme 8.94). To avoid the drastic conditions required by the hypobromite method, two new Hofmann-like reagents, iodosobenzene and /-hydroxy-Z-p-tolucnesulfonyloxyiodobcnzcnc (HTIB), have been introduced. Under these conditions, the rearrangement takes place smoothly to produce the desired aminoalkylphosphonic acids in high yields (65-93%). ... 

A.D., Howard, A., Sheldrick, G.M., Mariano-Dunaway, D., and Herzberg, O. (2002) Degradation pathway of the phos-phonate ciliatine crystal stmcture of 2-aminoethylphosphonate transaminase. Biochemistry, 41 (44), 13162-13169. 

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