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Escherichia coli K-12 substr. MG1655 Pathway: superpathway of β-D-glucuronide and D-glucuronate degradation

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Locations of Mapped Genes:

Genetic Regulation Schematic: ?

Synonyms: D-glucuronate catabolism, D-glucuronate degradation, glucuronic acid degradation, glucuronate degradation, β-D-glucuronide degradation

Superclasses: Degradation/Utilization/Assimilation Carboxylates Degradation Sugar Acids Degradation D-Glucuronate Degradation
Degradation/Utilization/Assimilation Secondary Metabolites Degradation Sugar Derivatives Degradation Sugar Acids Degradation D-Glucuronate Degradation
Superpathways

Summary:
E. coli can use β-D-glucuronides and the hexuronates D-glucuronate and D-fructuronate and as the sole sources of carbon for growth. β-D-glucuronides are detoxification products that are excreted into the mammalian gut in the bile. D-glucuronate is found in animal mucus and at low levels in plant tissues. The enzymes of this pathway were first described in a series of publications by Ashwell et al. [Ashwell58, Ashwell60, Hickman60, Smiley60, Cynkin60].

The initial step in the degradation of β-glucuronides is hydrolysis by β-D-glucuronidase to yield D-glucuronate, which is subsequently isomerized to D-fructuronate by D-glucuronate isomerase, an enzyme which can carry out the analogous function in the D-galacturonate degradation I pathway. D-fructuronate then undergoes an NADH-dependent reduction to D-mannonate by D-mannonate oxidoreductase. D-mannonate dehydratase subsequently catalyzes dehydration to yield 2-dehydro-3-deoxy-D-gluconate. At this point, the superpathway of β-D-glucuronide and D-glucuronate degradation and D-galacturonate degradation I pathways converge, and a common enzyme, 2-keto-3-deoxygluconokinase, phosphorylates 2-dehydro-3-deoxy-D-gluconate to yield 2-dehydro-3-deoxy-D-gluconate-6-phosphate, which enters central metabolism via the Entner-Doudoroff pathway I.

Review: Mandrand-Berthelot, M.-A., Condemine, G., and Hugouvieux-Cotte-Pattat, N., EcoSal Module 3.4.2 [ECOSAL]

Superpathways: superpathway of hexuronide and hexuronate degradation

Subpathways: β-D-glucuronide and D-glucuronate degradation , D-fructuronate degradation

Credits:
Created 09-Sep-1994 by Riley M , Marine Biological Laboratory
Last-Curated ? 04-Feb-2008 by Keseler I , SRI International


References

Ashwell58: Ashwell A, Wahba AJ, Hickman J (1958). "A new pathway of uronic acid metabolism." Biochim Biophys Acta 30(1);186-7. PMID: 13584413

Ashwell60: Ashwell G, Wahba AJ, Hickman J (1960). "Uronic acid metabolism in bacteria. I. Purification and properties of uronic acid isomerase in Escherichia coli." J Biol Chem 1960;235(6):1559-1565. PMID: 13794771

Cynkin60: Cynkin MA, Ashwell G (1960). "Uronic acid metabolism in bacteria. IV. Purification and properties of 2-keto-3-deoxy-D-gluconokinase in Escherichia coli." J Biol Chem 235;1576-9. PMID: 13813474

ECOSAL: "Escherichia coli and Salmonella: Cellular and Molecular Biology." Online edition.

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;1566-70. PMID: 14401695

Smiley60: Smiley JD, Ashwell G (1960). "Uronic acid metabolism in bacteria. III. Purification and properties of D-altronic acid and D-mannonic acid dehydrases in Escherichia coli." J Biol Chem 235;1571-5. PMID: 13831814

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Adams90a: Adams MR, Grubb SM, Hamer A, Clifford MN (1990). "Colorimetric enumeration of Escherichia coli based on beta-glucuronidase activity." Appl Environ Microbiol 56(7);2021-4. PMID: 2202252

Aich01: Aich S, Delbaere LT, Chen R (2001). "Expression and purification of Escherichia coli beta-glucuronidase." Protein Expr Purif 22(1);75-81. PMID: 11388802

Blanco82: Blanco C, Ritzenthaler P, Mata-Gilsinger M (1982). "Cloning and endonuclease restriction analysis of uidA and uidR genes in Escherichia coli K-12: determination of transcription direction for the uidA gene." J Bacteriol 149(2);587-94. PMID: 6276362

Blanco87: Blanco C, Nemoz G (1987). "One step purification of Escherichia coli beta-glucuronidase." Biochimie 69(2);157-61. PMID: 3105604

BRENDA14: BRENDA team (2014). "Imported from BRENDA version existing on Aug 2014." http://www.brenda-enzymes.org.

Chen07a: Chen KC, Cheng TL, Leu YL, Prijovich ZM, Chuang CH, Chen BM, Roffler SR (2007). "Membrane-localized activation of glucuronide prodrugs by beta-glucuronidase enzymes." Cancer Gene Ther 14(2);187-200. PMID: 16977328

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

DidierFichet68: Didier-Fichet ML, Stoeber F (1968). "[On the properties and the biosynthesis of beta-glucuronidase of Escherichia coli K 12]." C R Acad Sci Hebd Seances Acad Sci D 266(19);2021-4. PMID: 4970455

Doyle55: Doyle ML, Katzman PA, Doisy EA (1955). "Production and properties of bacterial beta-glucuronidase." J Biol Chem 217(2);921-30. PMID: 13271452

Dreyer87: Dreyer JL (1987). "The role of iron in the activation of mannonic and altronic acid hydratases, two Fe-requiring hydro-lyases." Eur J Biochem 166(3);623-30. PMID: 3038546

Egan92: Egan SE, Fliege R, Tong S, Shibata A, Wolf RE, Conway T (1992). "Molecular characterization of the Entner-Doudoroff pathway in Escherichia coli: sequence analysis and localization of promoters for the edd-eda operon." J Bacteriol 1992;174(14);4638-46. PMID: 1624451

Flores02: Flores H, Ellington AD (2002). "Increasing the thermal stability of an oligomeric protein, beta-glucuronidase." J Mol Biol 315(3);325-37. PMID: 11786015

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

Fradkin71: Fradkin JE, Fraenkel DG (1971). "2-keto-3-deoxygluconate 6-phosphate aldolase mutants of Escherichia coli." J Bacteriol 108(3);1277-83. PMID: 4945194

Geary11: Geary JR, Nijak GM, Larson SL, Talley JW (2011). "Hydrolysis of the soluble fluorescent molecule carboxyumbelliferyl-beta-D-glucuronide by E. coli beta-glucuronidase as applied in a rugged, in situ optical sensor." Enzyme Microb Technol 49(1);6-10. PMID: 22112264

Geddie04: Geddie ML, Matsumura I (2004). "Rapid evolution of beta-glucuronidase specificity by saturation mutagenesis of an active site loop." J Biol Chem 279(25);26462-8. PMID: 15069062

GOA01: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

GOA01a: GOA, MGI (2001). "Gene Ontology annotation based on Enzyme Commission mapping." Genomics 74;121-128.

Henrissat91: Henrissat B (1991). "A classification of glycosyl hydrolases based on amino acid sequence similarities." Biochem J 280 ( Pt 2);309-16. PMID: 1747104

Hickman60a: 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.

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Report Errors or Provide Feedback
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 Thu Nov 27, 2014, BIOCYC14B.