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Chemical Compound Review

HMDB00362     3-hydroxy-2-phosphonooxy- propanoic acid

Synonyms: AC1L18DY, 2-P-glycerate, 2-pg, 2553-59-5, 2PG, ...
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Disease relevance of phosphoglycerate


High impact information on phosphoglycerate


Biological context of phosphoglycerate

  • Enolase (2-phospho-D-glycerate hydrolase, EC has been identified as an anaerobic stress protein in Echinochloa oryzoides based on the homology of its internal amino acid sequence with those of enolases from other organisms, by immunological reactivity, and induction of catalytic activity during anaerobic stress [10].

Anatomical context of phosphoglycerate


Associations of phosphoglycerate with other chemical compounds

  • The equilibrium mixture of yeast enolase with substrate, 2-phospho-D-glycerate (2-PGA), and product, phosphoenolpyruvate (P-enolpyruvate), has been crystallized from solutions of poly(ethylene glycol) (PEG) at pH 8 [12].
  • Crystals have been successfully transferred to an artificial mother liquor, pH = 7.8, 20 mM in Mg(2+) and 5 mM in 2-phospho-D-glycerate [13].
  • Yeast enolase (2-phospho-D-glycerate hydrolyase, E.C. has been crystallized by vapor diffusion from a solution containing 22% PEG 4000, 100 mM Tris buffer pH = 9.3, 200 mM Li(2)SO(4) [13].
  • Titration of Mg2+ with enolase in the presence of 2-phosphoglycerate (PGA) and Zn2+, where Zn2+ binds specifically at site I, gives a 1/T2 for Mg2+ bound at site II of 4000 s-1 (chi = 0.49 MHz) [14].
  • Muscle enolase (2-phospho-D-glycerate hydrolase, EC and liver enolse from young and old rats have been purified to homogeneity and several properties of the respective young/old pairs, including Km, behavior on polyacrylamide gels, sensitivity to heat and specific activity have been compared [15].

Gene context of phosphoglycerate

  • In higher vertebrates, the glycolytic enzyme enolase (2-phospho-D-glycerate hydrolyase; EC is active as a dimeric protein formed from three subunits--alpha: ubiquitous, beta: muscle specific, and gamma: neuron specific--encoded by different genes [16].
  • When a purified preparation of rat alpha gamma enolase (2-phospho-D-glycerate hydrolyase, EC was applied to a chromatofocusing column, the enolase was almost completely dissociated and recombined to form alpha alpha and gamma gamma enolases, which were eluted at different fractions from the column [17].
  • The cross-reacting antigens were isolated and characterised as glyceraldehyde-3-phosphate dehydrogenase and 2-phospho-D-glycerate hydrolyase [18].
  • 1. The chromatography of rat brain enolase (2-phospho-D-glycerate hydrolyase, EC reveals three distinet components [19].


  1. Reverse protonation is the key to general acid-base catalysis in enolase. Sims, P.A., Larsen, T.M., Poyner, R.R., Cleland, W.W., Reed, G.H. Biochemistry (2003) [Pubmed]
  2. Octameric enolase from the hyperthermophilic bacterium Thermotoga maritima: purification, characterization, and image processing. Schurig, H., Rutkat, K., Rachel, R., Jaenicke, R. Protein Sci. (1995) [Pubmed]
  3. Characterization of a maize cDNA that complements an enolase-deficient mutant of Escherichia coli. Lal, S.K., Johnson, S., Conway, T., Kelley, P.M. Plant Mol. Biol. (1991) [Pubmed]
  4. Expression of gamma-subunit of enolase, neuron-specific enolase, in human non-neuroendocrine tumors and derived cell lines. Påhlman, S., Esscher, T., Nilsson, K. Lab. Invest. (1986) [Pubmed]
  5. Posttranscriptional and posttranslational control of enolase expression in the facultative Crassulacean acid metabolism plant Mesembryanthemum Crystallinum L. Forsthoefel, N.R., Cushman, M.A., Cushman, J.C. Plant Physiol. (1995) [Pubmed]
  6. Crystallization and preliminary crystallographic data for a tetragonal form of yeast enolase. Lebioda, L., Brewer, J.M. J. Mol. Biol. (1984) [Pubmed]
  7. Phosphoglycerate mutase from wheat germ: studies with isotopically labeled 3-phospho-D-glycerates showing that the catalyzed reaction is intramolecular. Appendix: phosphoglycerate mutase from wheat germ: isolation, crystallization, and properties. Leadlay, P.F., Breathnach, R., Gatehouse, J.A., Johnson, P.E., Knowles, J.R. Biochemistry (1977) [Pubmed]
  8. The carboxyphosphonoenolpyruvate synthase-encoding gene from the bialaphos-producing organism Streptomyces hygroscopicus. Lee, S.H., Hidaka, T., Nakashita, H., Seto, H. Gene (1995) [Pubmed]
  9. A comparative study of the distribution of alpha- and gamma-enolase subunits in cultured rat neural cells and fibroblasts. Deloulme, J.C., Helies, A., Ledig, M., Lucas, M., Sensenbrenner, M. Int. J. Dev. Neurosci. (1997) [Pubmed]
  10. Identification and gene expression of anaerobically induced enolase in Echinochloa phyllopogon and Echinochloa crus-pavonis. Fox, T.C., Mujer, C.V., Andrews, D.L., Williams, A.S., Cobb, B.G., Kennedy, R.A., Rumpho, M.E. Plant Physiol. (1995) [Pubmed]
  11. Characterization of alpha alpha, beta beta, gamma gamma and alpha gamma human enolase isozymes, and preparation of hybrid enolases (alpha gamma, beta gamma and alpha beta) from homodimeric forms. Shimizu, A., Suzuki, F., Kato, K. Biochim. Biophys. Acta (1983) [Pubmed]
  12. A carboxylate oxygen of the substrate bridges the magnesium ions at the active site of enolase: structure of the yeast enzyme complexed with the equilibrium mixture of 2-phosphoglycerate and phosphoenolpyruvate at 1.8 A resolution. Larsen, T.M., Wedekind, J.E., Rayment, I., Reed, G.H. Biochemistry (1996) [Pubmed]
  13. Crystallization at low salt concentration and alkaline pH and preliminary crystallographic data for a monoclinic form of yeast enolase. Zhang, E., Lebioda, L., Chen, Y., Brewer, J.M., Hatada, M., Minor, W. Acta Crystallogr. D Biol. Crystallogr. (1994) [Pubmed]
  14. 25Mg NMR studies of yeast enolase and rabbit muscle pyruvate kinase. Lee, M.E., Nowak, T. Arch. Biochem. Biophys. (1992) [Pubmed]
  15. Effect of aging on enolase from rat muscle, liver and heart. Rothstein, M., Coppens, M., Sharma, H.K. Biochim. Biophys. Acta (1980) [Pubmed]
  16. The beta enolase subunit displays three different patterns of microheterogeneity in human striated muscle. Merkulova, T., Thornell, L.E., Butler-Browne, G., Oberlin, C., Lucas, M., Lamandé, N., Lazar, M., Keller, A. J. Muscle Res. Cell. Motil. (1999) [Pubmed]
  17. Purification of two enolases from human brain using a chromatofocusing column. Shimizu, A., Suzuki, F., Kato, K. Biochim. Biophys. Acta (1982) [Pubmed]
  18. Molecular mimicry by Mycoplasma pneumoniae to evade the induction of adherence inhibiting antibodies. Jacobs, E., Bartl, A., Oberle, K., Schiltz, E. J. Med. Microbiol. (1995) [Pubmed]
  19. Enolase isoenzymes. III. Chromatographic and immunological characteristics of rat brain enolase. Fletcher, L., Rider, C.C., Taylor, C.B. Biochim. Biophys. Acta (1976) [Pubmed]
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