Escherichia coli K-12 substr. MG1655 Compound Class: D-fructuronate

Synonyms: fructuronate

Superclasses: an acidall carboxy acidsa carboxylatea monocarboxylatea uronatea hexuronate

D-fructuronate compound structure

Chemical Formula: C6H9O7

Child Classes: D-fructofuranuronate (1)

Component of: UxuR-fructuronate

Citations: [Hickman60]

Molecular Weight: 193.13 Daltons

Monoisotopic Molecular Weight: 194.0426526757 Daltons

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

Unification Links: ChEBI:4126, IAF1260:36345, KEGG:C00905, PubChem:439343

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -261.4 [Forsythe97]

Reactions known to produce the compound:

Not in pathways:
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
a 1-acyl 2-lyso-phosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+

Reactions known to both consume and produce the compound:

β-D-glucuronide and D-glucuronate degradation :
aldehydo-D-glucuronate ↔ D-fructuronate

D-fructuronate degradation :
D-mannonate + NAD+D-fructuronate + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
D-fructuronate + UxuR = UxuR-fructuronate

Not in pathways:
a 2-acyl 1-lyso-phosphatidylcholine + H2O = a carboxylate + sn-glycero-3-phosphocholine + H+
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]

In Transport reactions:
D-fructuronate[periplasm] + H+[periplasm]D-fructuronate[cytosol] + H+[cytosol]

Enzymes inhibited by D-fructuronate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: altronate oxidoreductase [Portalier72, Comment 1]


Forsythe97: Forsythe RG, Karp PD, Mavrovouniotis ML (1997). "Estimation of Equilibrium Constants Using Automated Group Contribution Methods." CABIOS 13(5):537-543.

Hickman60: Hickman, J., Ashwell, G. (1960). "Uronic Acid Metabolism in Bacteria: II. Purification and properties of D-altronic acid and D-mannonic acid dehydrogenases in Escherichia coli." J. Biol. Chem. 235:1566-1570.

Portalier72: Portalier RC (1972). "[D-altronate: NAD-oxidoreductase from Escherichia coli K12. Kinetic studies]." Eur J Biochem 1972;30(2);211-9. PMID: 4351434

Portalier72a: Portalier RC, Stoeber FR (1972). "[D-altronate: NAD-oxidoreductase in Escherichia coli K12. Purification, properties, and specificity]." Eur J Biochem 1972;26(1);50-61. PMID: 4402917

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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