EC Number   |
Substrates |
Organism |
Products |
Reversibility |
|---|
  1.13.11.72 | (2R)-hydroxypropylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
2-oxopropylphosphonate + hydroxymethylphosphonate + acetate |
substrate partitions between conversion to 2-oxopropylphosphonate and hydroxymethylphosphonate |
? |
| 1.13.11.72 | (R)-2-hydroxyethylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
hydroxymethylphosphonate + formate |
product is almost racemic |
? |
| 1.13.11.72 | (S)-2-hydroxyethylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
hydroxymethylphosphonate + formate |
product is almost racemic |
? |
| 1.13.11.72 | 1-hydroxy-2,2,2-trifluoroethylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
trifluoroacetylphosphonate |
- |
? |
| 1.13.11.72 | 1-hydroxyethylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
acetylphosphate |
- |
? |
| 1.13.11.72 | 2-hydroxyethylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
hydroxymethylphosphonate + formate |
- |
? |
| 1.13.11.72 | 2-hydroxyethylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
hydroxymethylphosphonate + formate |
- |
ir |
| 1.13.11.72 | 2-hydroxyethylphosphonate + O2 |
- |
Streptomyces viridochromogenes |
hydroxymethylphosphonate + formate |
all four electrons required for reduction of O2 are provided by the substrate. Occurence of an intermediate species in which oxygen derived from O2 exchanges with water |
? |
| 1.13.11.72 | 2-hydroxyethylphosphonate + O2 |
catalytic cycle is based on concatenated bifurcations. The first bifurcation is based on the abstraction of hydrogen atoms from the substrate, which leads to a distal or proximal hydroperoxo species Fe-OOH or Fe-(OH)O. The second and the third bifurcations refer to the carbon-carbon bond cleavage reaction achieved through a tridentate intermediate, or employing a proton-shuttle assisted mechanism, in which the residue Glu176 or the FeIV O group serves as a general base. The reaction directions seem to be tunable and show significant environment dependence |
Streptomyces viridochromogenes |
hydroxymethylphosphonate + formate |
- |
? |
| 1.13.11.72 | 2-hydroxyethylphosphonate + O2 |
in the reaction mechanism water molecules serve as an oxygen source in the generation of mononuclear nonheme iron oxo complexes, taking part in the catalytic cycle before the carbon-carbon bond cleavage process. After the dioxygen is bound to the iron center, the dioxygen-bound species Fe-O2 is generated. The abstraction of hydrogen atom from the substrate leads to a distal or proximal hydroperoxo species Fe(III)-OOH. This is the rate-limiting step, which has an energy barrier of 21 and 18 kcal/mol for distal and proximal H-abstraction processes, respectively. The second step is the cleavage of the O-O bond, and the carbon-carbon bond is broken subsequently. In this step, a tridentate binding species and a Fe(IV) sigmaO species are important intermediates to break the carbon-carbon bond. In the third step, the formic acid and the intermediate CH2PO2(OH)- radical are generated. Finally, 2-hydroxyethylphosphonate is converted to hydroxymethylphosphonate, and the formate or formic acid is formed |
Streptomyces viridochromogenes |
hydroxymethylphosphonate + formate |
- |
? |
