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Chemical Compound Review:

Fluoropyruvate 3-fluoro-2-oxo-propanoic acid

Synonyms: CHEMBL1162543, CHEBI:55521, NSC-21734, AC1Q4OPL, NSC21734, ...

Flournoy, D.S. et al., Hoving, H. et al., Darland, G.K. et al., Garbe, T.R. et al., Saumweber, H. et al., et al.

Akita, Nishimori, Shimamoto, Fujii, Iefuji,

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Disease relevance of Fluoropyruvic acid

Inactivation of the pyruvate dehydrogenase complex of Escherichia coli by fluoropyruvate [1].

High impact information on Fluoropyruvic acid

Both (Z)- and (E)-F-PEP partition between carboxylation to produce 3-fluorooxalacetate and hydrolysis to produce 3-fluoropyruvate [2].
The pyruvate dehydrogenase complex (PDH complex) of Escherichia coli and its pyruvate dehydrogenase component (E1) are rapidly inactivated by low concentrations of fluoropyruvate in a thiamin pyrophosphate (TPP) dependent process [1].
Fluoropyruvate is known to generate acetyl-TPP at the active site of E1 [1].
Transcarboxylase, coupled to malate dehydrogenase, has been used to analyze samples of chiral fluoropyruvate obtained by dephosphorylation of (Z)-fluorophosphoenolpyruvate in D2O in the presence of either pyruvate kinase or enzyme I from the Escherichia coli sugar transport systems [3].
Thiomethylated lactate dehydrogenase was able to form an abortive adduct between NAD+ and fluoropyruvate [4].

Biological context of Fluoropyruvic acid

After 3 days, 10-36% of the colonies showed RFLPs, but the type was now dominated by the fluoropyruvate-specific RFLP, which, at higher resolution, invariably proved to be heterogeneous [5].

Associations of Fluoropyruvic acid with other chemical compounds

An inhibition, competitive to pyruvate, of the pyruvate dehydrogenase component (Ki = 18 microM) by fluoropyruvate was observed with both enzyme forms [6].
Primary metabolism of DFA involves its oxidation to fluoropyruvate (FP); this organic fluoride is then rapidly reduced to fluorolactate (FL) which is the major organic metabolite in laboratory animals [7].
Inactivation of flavocytochrome b2 with fluoropyruvate. Reaction at the active-site histidine [8].

Gene context of Fluoropyruvic acid

Fluoropyruvate is described as a first inhibitor of DXP synthase [9].
Mutants of laboratory strain No. 5022 ((a) his(2,6), ura3) deficient in pyruvate uptake were isolated from fluoropyruvate resistant mutants [10].

References

Inactivation of the pyruvate dehydrogenase complex of Escherichia coli by fluoropyruvate. Flournoy, D.S., Frey, P.A. Biochemistry (1989) [Pubmed]
Mechanistic studies of phosphoenolpyruvate carboxylase from Zea mays with (Z)- and (E)-3-fluorophosphoenolpyruvate as substrates. Janc, J.W., Urbauer, J.L., O'Leary, M.H., Cleland, W.W. Biochemistry (1992) [Pubmed]
Fluorine NMR studies on stereochemical aspects of reactions catalyzed by transcarboxylase, pyruvate kinase, and enzyme I. Hoving, H., Crysell, B., Leadlay, P.F. Biochemistry (1985) [Pubmed]
A detailed investigation of the properties of lactate dehydrogenase in which the 'Essential' cysteine-165 is modified by thioalkylation. Bloxham, D.P., Sharma, R.P., Wilton, D.C. Biochem. J. (1979) [Pubmed]
Inhibitor-associated transposition events in Corynebacterium glutamicum. Garbe, T.R., Suzuki, N., Inui, M., Yukawa, H. Mol. Genet. Genomics (2004) [Pubmed]
Pyruvate dehydrogenase component of the pyruvate dehydrogenase complex from Escherichia coli K12. Purification and characterization. Saumweber, H., Binder, R., Bisswanger, H. Eur. J. Biochem. (1981) [Pubmed]
Oxidative and defluorinative metabolism of fludalanine, 2-2H-3-fluoro-D-alanine. Darland, G.K., Hajdu, R., Kropp, H., Kahan, F.M., Walker, R.W., Vandenheuvel, W.J. Drug Metab. Dispos. (1986) [Pubmed]
Inactivation of flavocytochrome b2 with fluoropyruvate. Reaction at the active-site histidine. Urban, P., Lederer, F. Eur. J. Biochem. (1988) [Pubmed]
Tools for discovery of inhibitors of the 1-deoxy-D-xylulose 5-phosphate (DXP) synthase and DXP reductoisomerase: an approach with enzymes from the pathogenic bacterium Pseudomonas aeruginosa. Altincicek, B., Hintz, M., Sanderbrand, S., Wiesner, J., Beck, E., Jomaa, H. FEMS Microbiol. Lett. (2000) [Pubmed]
Transport of pyruvate in Saccharomyces cerevisiae and cloning of the gene encoded pyruvate permease. Akita, O., Nishimori, C., Shimamoto, T., Fujii, T., Iefuji, H. Biosci. Biotechnol. Biochem. (2000) [Pubmed]

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