Reaction: phosphonoacetaldehyde + H2O = acetaldehyde + phosphate
For diagram of reaction click here.
Other name(s): phosphonatase; 2-phosphonoacetylaldehyde phosphonohydrolase
Systematic name: 2-oxoethylphosphonate phosphonohydrolase
Comments: This enzyme destabilizes the C-P bond, by forming an imine between one of its lysine residues and the carbonyl group of the substrate, thus allowing this, normally stable, bond to be broken. The mechanism is similar to that used by EC 18.104.22.168, fructose-bisphosphate aldolase, to break a C-C bond. Belongs to the haloacetate dehalogenase family.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, PDB, CAS registry number: 37289-42-2
1. La Nauze, J.M. and Rosenberg, H. The identification of 2-phosphonoacetaldehyde as an intermediate in the degradation of 2-aminoethylphosphonate by Bacillus cereus. Biochim. Biophys. Acta 165 (1968) 438-447. [PMID: 4982500]
2. La Nauze, J.M., Rosenberg, H. and Shaw, D.C. The enzymic cleavage of the carbon-phosphorus bond: purification and properties of phosphonatase. Biochim. Biophys. Acta 212 (1970) 332-350. [PMID: 4989158]
3. La Nauze, J.M., Coggins, J.R. and Dixon, H.B.F. Aldolase-like imine formation in the mechanism of action of phosphonoacetaldehyde hydrolase. Biochem. J. 165 (1977) 409-411. [PMID: 200222]
4. Olsen, D.B., Hepburn, T.W., Moos, M., Mariano, P.S. and Dunaway-Mariano, D. Substrate binding and catalytic groups of the P-C bond cleaving enzyme, phosphonoacetaldehyde hydrolase. Biochemistry 27 (1988) 2229-2234. [PMID: 3132206]
5. Baker, A.S., Ciocci, M.J., Metcalf, W.W., Kim, J., Babbitt, P.C., Wanner, B.L., Martin, B.M. and Dunaway-Mariano, D. Insights into the mechanism of catalysis by the P-C bond-cleaving enzyme phosphonoacetaldehyde hydrolase derived from gene sequence analysis and mutagenesis. Biochemistry 37 (1998) 9305-9315. [PMID: 9649311]