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Chemical Compound Review:

CHEBI:30935 2-oxo-3-phosphono-propanoic acid

Synonyms: CTK1F0234, FT-0673864, DB02522, AC1L983E, C02798, ...

Zhang, G. et al., Horigane, A. et al., Seidel, H.M. et al., Ternan, N.G. et al., Graupner, M. et al., et al.

Ternan, Hamilton, Quinn,

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Disease relevance of PHOSPHONOPYRUVATE

The phosphonopyruvate decarboxylase from Bacteroides fragilis [1].
Recombinant expression in Escherichia coli confirms that it encodes a functional PEP mutase with a Km apparent of 8 microM for phosphonopyruvate and a kcat of 12 s-1 [2].
The products of two adjacent genes in the chromosome of Methanococcus jannaschii are similar to the amino and carboxyl halves of phosphonopyruvate decarboxylase, the enzyme that catalyzes the second step of fosfomycin biosynthesis in Streptomyces wedmorensis [3].
A novel, inducible carbon-phosphorus bond cleavage enzyme, phosphonopyruvate hydrolase, was detected in cell-free extracts of Burkholderia cepacia Pal6, an environmental isolate capable of mineralising L-phosphonoalanine as carbon, nitrogen and phosphorus source [4].

High impact information on PHOSPHONOPYRUVATE

Thus although it was shown twenty years ago that the isotope label from [14C]glucose or from [32P]phosphoenolpyruvate is incorporated into 2-aminoethylphosphonate by the protozoan Tetrahymena pyriformis, the presumed stoichiometric transformation of phosphoenolpyruvate to phosphonopyruvate has never been demonstrated [5].
In this paper, we report the cloning and overexpression of the B. fragilis phosphonopyruvate decarboxylase gene (aepY), purification of the phosphonopyruvate decarboxylase recombinant protein, and the extensive characterization of the reaction that it catalyzes [1].
The homotrimeric (41,184-Da subunit) phosphonopyruvate decarboxylase catalyzes (kcat = 10.2 +/- 0.3 s-1) the decarboxylation of phosphonopyruvate (Km = 3.2 +/- 0.2 microm) to phosphonoacetaldehyde (Ki = 15 +/- 2 microm) and carbon dioxide at an optimal pH range of 7.0-7 [1].
The steady-state kinetic constants for catalysis of the conversion of phosphonopyruvate to phosphoenolpyruvate at pH 7.5 and 25 degrees C were measured at kcat = 34 s-1, phosphonopyruvate Km = 3 microM, and Mg2+ Km = 4 microM [6].
Theoretical studies of dissociative phosphoryl transfer in interconversion of phosphoenolpyruvate to phosphonopyruvate: solvent effects, thio effects, and implications for enzymatic reactions [7].

Biological context of PHOSPHONOPYRUVATE

Thus it appears that the main metabolic pathway of 2-amino-3-phosphonopropionic acid is deamination to produce 3-phosphonopyruvic acid which is, in turn, converted to 2-phosphonoacetaldehyde by decarboxylation, followed by both dephosphonylation and amination of the aldehyde to give acetaldehyde and 2-aminoethylphosphonic acid, respectively [8].

References

The phosphonopyruvate decarboxylase from Bacteroides fragilis. Zhang, G., Dai, J., Lu, Z., Dunaway-Mariano, D. J. Biol. Chem. (2003) [Pubmed]
Properties of phosphoenolpyruvate mutase, the first enzyme in the aminoethylphosphonate biosynthetic pathway in Trypanosoma cruzi. Sarkar, M., Hamilton, C.J., Fairlamb, A.H. J. Biol. Chem. (2003) [Pubmed]
Identification of the gene encoding sulfopyruvate decarboxylase, an enzyme involved in biosynthesis of coenzyme M. Graupner, M., Xu, H., White, R.H. J. Bacteriol. (2000) [Pubmed]
Initial in vitro characterisation of phosphonopyruvate hydrolase, a novel phosphate starvation-independent, carbon-phosphorus bond cleavage enzyme in Burkholderia cepacia Pal6. Ternan, N.G., Hamilton, J.T., Quinn, J.P. Arch. Microbiol. (2000) [Pubmed]
Phosphonate biosynthesis: isolation of the enzyme responsible for the formation of a carbon-phosphorus bond. Seidel, H.M., Freeman, S., Seto, H., Knowles, J.R. Nature (1988) [Pubmed]
Isolation and characterization of the carbon-phosphorus bond-forming enzyme phosphoenolpyruvate mutase from the mollusk Mytilus edulis. Kim, A., Kim, J., Martin, B.M., Dunaway-Mariano, D. J. Biol. Chem. (1998) [Pubmed]
Theoretical studies of dissociative phosphoryl transfer in interconversion of phosphoenolpyruvate to phosphonopyruvate: solvent effects, thio effects, and implications for enzymatic reactions. Xu, D., Guo, H., Liu, Y., York, D.M. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2005) [Pubmed]
Metabolism of 2-amino-3-phosphono[3-14C]propionic acid in cell-free preparations of rat liver. Horigane, A., Horiguchi, M., Matsumoto, T. Biochim. Biophys. Acta (1979) [Pubmed]

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