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discounted EARLY registration ends Dec 31, 2014
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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discounted EARLY registration ends Dec 31, 2014
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Escherichia coli K-12 substr. MG1655 Pathway: N-acetylneuraminate and N-acetylmannosamine degradation

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

Locations of Mapped Genes:

Genetic Regulation Schematic: ?

Superclasses: Degradation/Utilization/Assimilation Amines and Polyamines Degradation
Degradation/Utilization/Assimilation Carbohydrates Degradation Sugars Degradation

Summary:
Sialic acids are nine-carbon keto sugars that mediate a variety of cell-cell and cell-molecule interactions in eukaryotes and can be utilized by pathogens to evade the host immune response. Other bacteria, including E. coli K-12, can utilize N-acetylneuraminate, the most common form of sialic acid, as a sole source of carbon [Vimr85, Plumbridge99].

Production of the enzymes involved in N-acetylneuraminate degradation is induced by growth on sialic acid as the sole source of carbon, which is due to transcriptional regulation by the repressor NanR [Kalivoda03]. N-acetylmannosamine is only metabolized slowly by E. coli K-12, which may be due to low expression of an N-acetylmannosamine transporter and the predicted N-acetylmannosamine-6-phosphate epimerase in the absence of the inducer [Plumbridge99].

Please note that no biochemical data are available for the predicted N-acetylmannosamine-6-phosphate epimerase.

Reviews: [Vimr04]; C. Mayer and W. Boos, Hexose/Pentose and Hexitol/Pentitol Metabolism, EcoSal Module 3.4.1 [ECOSAL]

Superpathways: superpathway of N-acetylglucosamine, N-acetylmannosamine and N-acetylneuraminate degradation

Credits:
Created 23-Apr-2008 by Keseler I , SRI International
Last-Curated ? 23-Apr-2008 by Keseler I , SRI International


References

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

Kalivoda03: Kalivoda KA, Steenbergen SM, Vimr ER, Plumbridge J (2003). "Regulation of sialic acid catabolism by the DNA binding protein NanR in Escherichia coli." J Bacteriol 185(16);4806-15. PMID: 12897000

Plumbridge99: Plumbridge J, Vimr E (1999). "Convergent pathways for utilization of the amino sugars N-acetylglucosamine, N-acetylmannosamine, and N-acetylneuraminic acid by Escherichia coli." J Bacteriol 1999;181(1);47-54. PMID: 9864311

Vimr04: Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM (2004). "Diversity of microbial sialic acid metabolism." Microbiol Mol Biol Rev 68(1);132-53. PMID: 15007099

Vimr85: Vimr ER, Troy FA (1985). "Identification of an inducible catabolic system for sialic acids (nan) in Escherichia coli." J Bacteriol 164(2);845-53. PMID: 3902799

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

Aisaka91: Aisaka K, Igarashi A, Yamaguchi K, Uwajima T (1991). "Purification, crystallization and characterization of N-acetylneuraminate lyase from Escherichia coli." Biochem J 1991;276 ( Pt 2);541-6. PMID: 1646603

Angata02: Angata T, Varki A (2002). "Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective." Chem Rev 102(2);439-69. PMID: 11841250

Banerjee69: Banerjee S, Ghosh S (1969). "Purification and properties of N-acetylmannosamine kinase from Salmonella typhimurium." Eur J Biochem 8(2);200-6. PMID: 4889177

Campeotto09: Campeotto I, Carr SB, Trinh CH, Nelson AS, Berry A, Phillips SE, Pearson AR (2009). "Structure of an Escherichia coli N-acetyl-D-neuraminic acid lyase mutant, E192N, in complex with pyruvate at 1.45 angstrom resolution." Acta Crystallogr Sect F Struct Biol Cryst Commun 65(Pt 11);1088-90. PMID: 19923724

Campeotto10: Campeotto I, Bolt AH, Harman TA, Dennis C, Trinh CH, Phillips SE, Nelson A, Pearson AR, Berry A (2010). "Structural insights into substrate specificity in variants of N-acetylneuraminic Acid lyase produced by directed evolution." J Mol Biol 404(1);56-69. PMID: 20826162

Chang04: Chang DE, Smalley DJ, Tucker DL, Leatham MP, Norris WE, Stevenson SJ, Anderson AB, Grissom JE, Laux DC, Cohen PS, Conway T (2004). "Carbon nutrition of Escherichia coli in the mouse intestine." Proc Natl Acad Sci U S A 101(19);7427-32. PMID: 15123798

Chou11: Chou CY, Ko TP, Wu KJ, Huang KF, Lin CH, Wong CH, Wang AH (2011). "Modulation of substrate specificities of D-sialic acid aldolase through single mutations of Val-251." J Biol Chem 286(16);14057-64. PMID: 21270125

Cox02: Cox AD, Hood DW, Martin A, Makepeace KM, Deadman ME, Li J, Brisson JR, Moxon ER, Richards JC (2002). "Identification and structural characterization of a sialylated lacto-N-neotetraose structure in the lipopolysaccharide of Haemophilus influenzae." Eur J Biochem 269(16);4009-19. PMID: 12180977

Devenish09a: Devenish SR, Gerrard JA (2009). "The quaternary structure of Escherichia coli N-acetylneuraminate lyase is essential for functional expression." Biochem Biophys Res Commun 388(1);107-11. PMID: 19646958

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

Ferrero07: Ferrero MA, Martinez-Blanco H, Lopez-Velasco FF, Ezquerro-Saenz C, Navasa N, Lozano S, Rodriguez-Aparicio LB (2007). "Purification and characterization of GlcNAc-6-P 2-epimerase from Escherichia coli K92." Acta Biochim Pol 54(2);387-99. PMID: 17565386

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

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.

GOA06: GOA, SIB (2006). "Electronic Gene Ontology annotations created by transferring manual GO annotations between orthologous microbial proteins."

Gross88: Gross HJ, Brossmer R (1988). "Inhibition of N-acetylneuraminate lyase by N-acetyl-4-oxo-D-neuraminic acid." FEBS Lett 232(1);145-7. PMID: 2896604

Hood99: Hood DW, Makepeace K, Deadman ME, Rest RF, Thibault P, Martin A, Richards JC, Moxon ER (1999). "Sialic acid in the lipopolysaccharide of Haemophilus influenzae: strain distribution, influence on serum resistance and structural characterization." Mol Microbiol 33(4);679-92. PMID: 10447878

Hopkins13: Hopkins AP, Hawkhead JA, Thomas GH (2013). "Transport and catabolism of the sialic acids N-glycolylneuraminic acid and 3-keto-3-deoxy-D-glycero-D-galactonononic acid by Escherichia coli K-12." FEMS Microbiol Lett 347(1);14-22. PMID: 23848303

Hsu05: Hsu CC, Hong Z, Wada M, Franke D, Wong CH (2005). "Directed evolution of D-sialic acid aldolase to L-3-deoxy-manno-2-octulosonic acid (L-KDO) aldolase." Proc Natl Acad Sci U S A 102(26);9122-6. PMID: 15967977

Ishihama08: Ishihama Y, Schmidt T, Rappsilber J, Mann M, Hartl FU, Kerner MJ, Frishman D (2008). "Protein abundance profiling of the Escherichia coli cytosol." BMC Genomics 9;102. PMID: 18304323

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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
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