| Entry |
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| Name |
phosphonoacetaldehyde hydrolase;
phosphonatase;
2-phosphonoacetylaldehyde phosphonohydrolase
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| Class |
Hydrolases;
Acting on carbon-phosphorus bonds;
Acting on carbon-phosphorus bonds (only sub-subclass identified to date)
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| Sysname |
2-oxoethylphosphonate phosphonohydrolase
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| Reaction(IUBMB) |
phosphonoacetaldehyde + H2O = acetaldehyde + phosphate [RN: R00747]
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| Reaction(KEGG) |
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| Substrate |
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| Product |
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| Comment |
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 4.1.2.13, fructose-bisphosphate aldolase, to break a C-C bond. Belongs to the haloacetate dehalogenase family.
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| History |
EC 3.11.1.1 created 1972, modified 1976, modified 2001
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| Pathway |
| ec00440 | Phosphonate and phosphinate metabolism |
| ec01120 | Microbial metabolism in diverse environments |
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| Orthology |
| K05306 | phosphonoacetaldehyde hydrolase |
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| Genes |
» show all
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| Reference |
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| Authors |
La Nauze JM, Rosenberg H. |
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| Title |
The identification of 2-phosphonoacetaldehyde as an intermediate in the degradation of 2-aminoethylphosphonate by Bacillus cereus. |
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| Journal |
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| Reference |
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| Authors |
La Nauze JM, Rosenberg H, Shaw DC. |
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| Title |
The enzymic cleavage of the carbon-phosphorus bond: purification and properties of phosphonatase. |
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| Journal |
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| Reference |
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| Authors |
La Nauze JM, Coggins JR, Dixon HB. |
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| Title |
Aldolase-like imine formation in the mechanism of action of phosphonoacetaldehyde hydrolase. |
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| Journal |
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| Reference |
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| Authors |
Olsen DB, Hepburn TW, Moos M, Mariano PS, Dunaway-Mariano D. |
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| Title |
Investigation of the Bacillus cereus phosphonoacetaldehyde hydrolase. Evidence for a Schiff base mechanism and sequence analysis of an active-site peptide containing the catalytic lysine residue. |
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| Journal |
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| Reference |
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| Authors |
Baker AS, Ciocci MJ, Metcalf WW, Kim J, Babbitt PC, Wanner BL, Martin BM, Dunaway-Mariano D |
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| Title |
Insights into the mechanism of catalysis by the P-C bond-cleaving enzyme phosphonoacetaldehyde hydrolase derived from gene sequence analysis and mutagenesis. |
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| Journal |
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| Sequence |
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| Other DBs |
| ExplorEnz - The Enzyme Database: | 3.11.1.1 |
| ExPASy - ENZYME nomenclature database: | 3.11.1.1 |
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| LinkDB |
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