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Escherichia coli K-12 substr. MG1655 Compound: 3-phospho-D-glycerate

Synonyms: 3-phospho-(R)-glycerate, 3-phospho-D-glyceric acid, 3-P-D-glycerate, D-glycerate-3-P, D-glycerate 3-phosphate, 3-phosphoglycerate, D-3-phosphoglycerate

Superclasses: a glycerate 2/3-phospho-D-glycerate

Chemical Formula: C3H4O7P

Molecular Weight: 183.03 Daltons

Monoisotopic Molecular Weight: 185.9929390894 Daltons

SMILES: C(OP(=O)([O-])[O-])C(O)C(=O)[O-]

InChI: InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/p-3/t2-/m1/s1

InChIKey: InChIKey=OSJPPGNTCRNQQC-UWTATZPHSA-K

Unification Links: CAS:820-11-1 , ChEBI:58272 , HMDB:HMDB60180 , IAF1260:34230 , KEGG:C00197 , MetaboLights:MTBLC58272 , PubChem:25245548

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -369.39

Reactions known to produce the compound:

glycolate and glyoxylate degradation I :
D-glycerate + ATP → 3-phospho-D-glycerate + ADP + H+

Reactions known to both consume and produce the compound:

gluconeogenesis I :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycolysis I (from glucose-6P) :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

glycolysis II (from fructose-6P) :
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
2-phospho-D-glycerate ↔ 3-phospho-D-glycerate
3-phospho-D-glycerate + ATP ↔ 1,3-bisphospho-D-glycerate + ADP

serine biosynthesis :
3-phospho-D-glycerate + NAD+ ↔ 3-phospho-hydroxypyruvate + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
a [protein]-L-histidine + 2,3-diphospho-D-glycerate = a protein-Nπ-phospho-L-histidine + 3-phospho-D-glycerate


a protein-Nπ-phospho-L-histidine + 2/3-phospho-D-glycerate = a [protein]-L-histidine + 2,3-diphospho-D-glycerate
a [protein]-L-histidine + 2,3-diphospho-D-glycerate = a protein-Nπ-phospho-L-histidine + 2/3-phospho-D-glycerate

Enzymes activated by 3-phospho-D-glycerate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoglycerate kinase , isocitrate dehydrogenase phosphatase [Miller00]

Enzymes inhibited by 3-phospho-D-glycerate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glycerol-3-phosphate dehydrogenase, aerobic [Schryvers78] , isocitrate lyase [Comment 1]

Inhibitor (Noncompetitive) of: α-ketoglutarate reductase [Zhao96]

Inhibitor (Mechanism unknown) of: isocitrate dehydrogenase kinase [Miller00] , methylglyoxal synthase [Hopper71, Hopper72, Comment 2] , glutamine synthetase adenylyltransferase [Ebner70a, Comment 3]

In Growth Media: PMA phosphorus source test + 3-phospho-D-glycerate


References

Ebner70a: Ebner E, Wolf D, Gancedo C, Elsasser S, Holzer H (1970). "ATP: glutamine synthetase adenylyltransferase from Escherichia coli B. Purification and properties." Eur J Biochem 1970;14(3);535-44. PMID: 4920894

Hopper71: Hopper DJ, Cooper RA (1971). "The regulation of Escherichia coli methylglyoxal synthase; a new control site in glycolysis?." FEBS Lett 13(4);213-216. PMID: 11945670

Hopper72: Hopper DJ, Cooper RA (1972). "The purification and properties of Escherichia coli methylglyoxal synthase." Biochem J 1972;128(2);321-9. PMID: 4563643

Ko89: Ko YH, Vanni P, McFadden BA (1989). "The interaction of 3-phosphoglycerate and other substrate analogs with the glyoxylate- and succinate-binding sites of isocitrate lyase." Arch Biochem Biophys 1989;274(1);155-60. PMID: 2673042

Miller00: Miller SP, Chen R, Karschnia EJ, Romfo C, Dean A, LaPorte DC (2000). "Locations of the regulatory sites for isocitrate dehydrogenase kinase/phosphatase." J Biol Chem 275(2);833-9. PMID: 10625615

Schryvers78: Schryvers A, Lohmeier E, Weiner JH (1978). "Chemical and functional properties of the native and reconstituted forms of the membrane-bound, aerobic glycerol-3-phosphate dehydrogenase of Escherichia coli." J Biol Chem 253(3);783-8. PMID: 340460

Zhao96: Zhao G, Winkler ME (1996). "A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria." J Bacteriol 1996;178(1);232-9. PMID: 8550422


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Sat Dec 20, 2014, BIOCYC13A.