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Escherichia coli K-12 substr. MG1655 Pathway: GDP-mannose biosynthesis

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

Locations of Mapped Genes:

Genetic Regulation Schematic: ?

Superclasses: Biosynthesis Carbohydrates Biosynthesis Sugars Biosynthesis Sugar Nucleotides Biosynthesis GDP-sugar Biosynthesis

Summary:
General Background

In E. coli K-12 GDP-alpha-D-mannose is a precursor for the biosynthesis of GDP-L-fucose, as indicated in the pathway link. GDP-L-fucose is the nucleotide-activated form of L-fucose, a monosaccharide constituent of colanic acid. In the Enterobacteriaceae colanic acid (M antigen) is a polyanionic extracellular heteropolysaccharide containing a repeat unit with D-glucose, L-fucose, D-galactose, and D-glucuronate sugars that are nonstoichiometrically decorated with O-acetyl and pyruvate side chains [Grant69, Garegg71] (see pathway colanic acid building blocks biosynthesis).

In other bacteria, GDP-alpha-D-mannose is a precursor or participant in the synthesis of deoxyhexoses, oligosaccharides, polysaccharides and organic solutes. In eukaryotes GDP-alpha-D-mannose is a key substrate in glycoconjugate formation and is a precursor for the biosynthesis of important compounds. Examples of such pathways are listed in MetaCyc under compound GDP-α-D-mannose.

About This Pathway

The first two enzymes in the pathway catalyze isomerizations that interconvert phosphorylated aldohexoses (β-D-glucose-6-phosphate, D-mannose-6-phosphate) and phosphorylated ketohexoses (D-fructose-6-phosphate). The reaction catalyzed by mannose-6-phosphate isomerase that produces D-mannose-6-phosphate is the first committed step in the biosynthesis of the activated mannose donor GDP-α-D-mannose. D-mannose-6-phosphate is then converted to GDP-D-mannose by the action of phosphomannomutase and mannose-1-phosphate guanylyltransferase [Gao05a, Stevenson96].

Genetically engineered variants of this pathway in E. coli have been reported and are potentially useful in the production of mannosylglycerate [Sampaio03] and fucosyloligosaccharides [Honghong11].

Superpathways: colanic acid building blocks biosynthesis

Credits:
Created 13-Sep-2007 by Caspi R , SRI International
Last-Curated ? 31-Jan-2013 by Fulcher C , SRI International


References

Gao05a: Gao H, Chen Y, Leary JA (2005). "Kinetic measurements of phosphoglucose isomerase and phosphomannose isomerase by direct analysis of phosphorylated aldose-ketose isomers using tandem mass spectrometry." International Journal of Mass Spectrometry 240(3);291-299.

Garegg71: Garegg PJ, Lindberg B, Onn T, Sutherland IW (1971). "Comparative structural studies on the M-antigen from Salmonella typhimurium. Escherichia coli and Aerobacter cloacae." Acta Chem Scand 25(6);2103-8. PMID: 4941627

Grant69: Grant WD, Sutherland IW, Wilkinson JF (1969). "Exopolysaccharide colanic acid and its occurrence in the Enterobacteriaceae." J Bacteriol 100(3);1187-93. PMID: 4902806

Honghong11: Honghong J, Fuping L, Yu L, Xiaoguang L, Yihan L, Hongbin W, Jing L, Yueting C (2011). "Synthesis of GDP-mannose using coupling fermentation of recombinant Escherichia coli." Biotechnol Lett 33(6);1145-50. PMID: 21293904

Markovitz67: Markovitz A, Sydiskis RJ, Lieberman MM (1967). "Genetic and biochemical studies on mannose-negative mutants that are deficient in phosphomannose isomerase in Escherichia coli K-12." J Bacteriol 94(5);1492-6. PMID: 4862193

Sampaio03: Sampaio MM, Santos H, Boos W (2003). "Synthesis of GDP-mannose and mannosylglycerate from labeled mannose by genetically engineered Escherichia coli without loss of specific isotopic enrichment." Appl Environ Microbiol 69(1);233-40. PMID: 12514000

Stevenson96: Stevenson G, Andrianopoulos K, Hobbs M, Reeves PR (1996). "Organization of the Escherichia coli K-12 gene cluster responsible for production of the extracellular polysaccharide colanic acid." J Bacteriol 1996;178(16);4885-93. PMID: 8759852

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

Ahn11: Ahn J, Chung BK, Lee DY, Park M, Karimi IA, Jung JK, Lee H (2011). "NADPH-dependent pgi-gene knockout Escherichia coli metabolism producing shikimate on different carbon sources." FEMS Microbiol Lett 324(1);10-6. PMID: 22092758

Al12: Al Mamun AA, Lombardo MJ, Shee C, Lisewski AM, Gonzalez C, Lin D, Nehring RB, Saint-Ruf C, Gibson JL, Frisch RL, Lichtarge O, Hastings PJ, Rosenberg SM (2012). "Identity and function of a large gene network underlying mutagenic repair of DNA breaks." Science 338(6112);1344-8. PMID: 23224554

Aoyama94: Aoyama K, Haase AM, Reeves PR (1994). "Evidence for effect of random genetic drift on G+C content after lateral transfer of fucose pathway genes to Escherichia coli K-12." Mol Biol Evol 1994;11(6);829-38. PMID: 7815923

Bastin95: Bastin DA, Reeves PR (1995). "Sequence and analysis of the O antigen gene (rfb) cluster of Escherichia coli O111." Gene 1995;164(1);17-23. PMID: 7590310

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

Butland05: Butland G, Peregrin-Alvarez JM, Li J, Yang W, Yang X, Canadien V, Starostine A, Richards D, Beattie B, Krogan N, Davey M, Parkinson J, Greenblatt J, Emili A (2005). "Interaction network containing conserved and essential protein complexes in Escherichia coli." Nature 433(7025);531-7. PMID: 15690043

Byrne14: Byrne RT, Chen SH, Wood EA, Cabot EL, Cox MM (2014). "Surviving extreme exposure to ionizing radiation: Escherichia coli genes and pathways." J Bacteriol. PMID: 25049088

Canonaco01: Canonaco F, Hess TA, Heri S, Wang T, Szyperski T, Sauer U (2001). "Metabolic flux response to phosphoglucose isomerase knock-out in Escherichia coli and impact of overexpression of the soluble transhydrogenase UdhA." FEMS Microbiol Lett 204(2);247-52. PMID: 11731130

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

Charusanti10: Charusanti P, Conrad TM, Knight EM, Venkataraman K, Fong NL, Xie B, Gao Y, Palsson BO (2010). "Genetic basis of growth adaptation of Escherichia coli after deletion of pgi, a major metabolic gene." PLoS Genet 6(11);e1001186. PMID: 21079674

Csonka77: Csonka LN, Fraenkel DG (1977). "Pathways of NADPH formation in Escherichia coli." J Biol Chem 252(10);3382-91. PMID: 16899

Desvergnes12: Desvergnes S, Courtiol-Legourd S, Daher R, Dabrowski M, Salmon L, Therisod M (2012). "Synthesis and evaluation of malonate-based inhibitors of phosphosugar-metabolizing enzymes: class II fructose-1,6-bis-phosphate aldolases, type I phosphomannose isomerase, and phosphoglucose isomerase." Bioorg Med Chem 20(4);1511-20. PMID: 22269276

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

Elling96: Elling L, Ritter JE, Verseck S (1996). "Expression, purification and characterization of recombinant phosphomannomutase and GDP-alpha-D-mannose pyrophosphorylase from Salmonella enterica, group B, for the synthesis of GDP-alpha-D-mannose from D-mannose." Glycobiology 6(6);591-7. PMID: 8922954

Fong06: Fong SS, Nanchen A, Palsson BO, Sauer U (2006). "Latent pathway activation and increased pathway capacity enable Escherichia coli adaptation to loss of key metabolic enzymes." J Biol Chem 281(12);8024-33. PMID: 16319065

Foret09: Foret J, de Courcy B, Gresh N, Piquemal JP, Salmon L (2009). "Synthesis and evaluation of non-hydrolyzable D-mannose 6-phosphate surrogates reveal 6-deoxy-6-dicarboxymethyl-D-mannose as a new strong inhibitor of phosphomannose isomerases." Bioorg Med Chem 17(20);7100-7. PMID: 19783448

Fraenkel67: Fraenkel DG, Levisohn SR (1967). "Glucose and gluconate metabolism in an Escherichia coli mutant lacking phosphoglucose isomerase." J Bacteriol 93(5);1571-8. PMID: 5337843

Fraenkel67a: Fraenkel DG (1967). "Genetic mapping of mutations affecting phosphoglucose isomerase and fructose diphosphatase in Escherichia coli." J Bacteriol 93(5);1582-7. PMID: 4290578

Friedberg72: Friedberg I (1972). "Localization of phosphoglucose isomerase in Escherichia coli and its relation to the induction of the hexose phosphate transport system." J Bacteriol 1972;112(3);1201-5. PMID: 4344919

Gao05b: Gao H, Yu Y, Leary JA (2005). "Mechanism and kinetics of metalloenzyme phosphomannose isomerase: measurement of dissociation constants and effect of zinc binding using ESI-FTICR mass spectrometry." Anal Chem 77(17);5596-603. PMID: 16131071

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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 Mon Nov 24, 2014, biocyc14.