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MetaCyc Pathway: O-antigen building blocks biosynthesis (E. coli)

Pathway diagram: O-antigen building blocks biosynthesis (E. coli)

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisCell Structures BiosynthesisLipopolysaccharide BiosynthesisO-Antigen Biosynthesis
Metabolic Clusters

Some taxa known to possess this pathway include : Escherichia coli K-12 substr. MG1655

Expected Taxonomic Range: Aquificae , Bacteroidetes/Chlorobi group, Caldiserica, Chlamydiae/Verrucomicrobia group, Chloroflexi , Chrysiogenetes , Cyanobacteria, Deferribacteres , Deinococcus-Thermus, Dictyoglomi , Elusimicrobia , Fibrobacteres/Acidobacteria group, Fusobacteria , Gemmatimonadetes , Nitrospirae, Planctomycetes, Proteobacteria, Spirochaetes , Synergistetes, Tenericutes, Thermodesulfobacteria , Thermotogae

Lipopolysaccharides (LPS) are a major outer membrane component of Gram-negative bacteria. Unlike the Gram-positives, which have a thick peptidoglycan layer, the Gram-negatives have a single layer of peptidoglycan between the inner and outer lipid bilayer membranes, but their surface is covered with lipopolysaccharides. The presence of LPS in the outer membrane confers stability to the bacterial membrane, protection against bacteriophages and the action of certain antibiotics, as well as protection against the host defence mechanism during infections.

LPS is composed of a lipid moiety (lipid A) that anchors the molecule in the outer membrane, and a polysaccharide moiety that extends out of the cell wall. The polysaccharide moiety is further divided into the core, which is an oligosaccharide consisting of an inner and outer region, and a distal repeating unit known as O-antigen.

The O-specific chain is the part of the LPS that shows the largest variation between species and the part that evokes a specific immune response. Some bacteria do not produce an O-antigen at all (the LPS of these organisms is called rough-type, because these bacteria produce colonies with rough edges when growing on agar plates).

All O-antigens are attached to the core and consist of repeated oligosaccharide units.

Escherichia coli K12 produces an O-antigen composed of four sugars: glucose, N-acetylglucosamine, galactose and rhamnose.

This pathway depicts the synthesis of three of these sugars. UDP-galactose is transformed from its pyranose form to its furanose form. dTTP glucose-1-phosphate is derivatized to dTDP-rhamnose. Fructose-6-phosphate gains an amino group, incorporates an acetate moiety and then acquires a nucleoside diphosphate resulting in UDP-N-acetyl-D-glucosamine. During formation of the repeat unit, the nucleoside diphosphates are removed.

The repeat unit is polymerized and attached to the outer core. Formation and polymerization of the O-antigen repeat unit is not shown here [Stevenson94, Liu94a, Neidhardt96].

Subpathways: dTDP-L-rhamnose biosynthesis I, UDP-N-acetyl-D-glucosamine biosynthesis I

Unification Links: EcoCyc:OANTIGEN-PWY


Delcour99: Delcour J, Ferain T, Deghorain M, Palumbo E, Hols P (1999). "The biosynthesis and functionality of the cell-wall of lactic acid bacteria." Antonie Van Leeuwenhoek 76(1-4);159-84. PMID: 10532377

Liu94a: Liu D, Reeves PR (1994). "Escherichia coli K12 regains its O antigen." Microbiology 140 ( Pt 1);49-57. PMID: 7512872

Neidhardt96: Neidhardt FC, Curtiss III R, Ingraham JL, Lin ECC, Low Jr KB, Magasanik B, Reznikoff WS, Riley M, Schaechter M, Umbarger HE "Escherichia coli and Salmonella, Cellular and Molecular Biology, Second Edition." American Society for Microbiology, Washington, D.C., 1996.

Stevenson94: Stevenson G, Neal B, Liu D, Hobbs M, Packer NH, Batley M, Redmond JW, Lindquist L, Reeves P (1994). "Structure of the O antigen of Escherichia coli K-12 and the sequence of its rfb gene cluster." J Bacteriol 1994;176(13);4144-56. PMID: 7517391

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

Aguirrezabalaga00: Aguirrezabalaga I, Olano C, Allende N, Rodriguez L, Brana AF, Mendez C, Salas JA (2000). "Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus." Antimicrob Agents Chemother 44(5);1266-75. PMID: 10770761

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

Allard00: Allard ST, Giraud MF, Whitfield C, Messner P, Naismith JH (2000). "The purification, crystallization and structural elucidation of dTDP-D-glucose 4,6-dehydratase (RmlB), the second enzyme of the dTDP-L-rhamnose synthesis pathway from Salmonella enterica serovar typhimurium." Acta Crystallogr D Biol Crystallogr 56(Pt 2);222-5. PMID: 10666612

Allard01: Allard ST, Giraud MF, Whitfield C, Graninger M, Messner P, Naismith JH (2001). "The crystal structure of dTDP-D-Glucose 4,6-dehydratase (RmlB) from Salmonella enterica serovar Typhimurium, the second enzyme in the dTDP-l-rhamnose pathway." J Mol Biol 307(1);283-95. PMID: 11243820

Allard04: Allard ST, Cleland WW, Holden HM (2004). "High resolution X-ray structure of dTDP-glucose 4,6-dehydratase from Streptomyces venezuelae." J Biol Chem 279(3);2211-20. PMID: 14570895

Arifuzzaman06: Arifuzzaman M, Maeda M, Itoh A, Nishikata K, Takita C, Saito R, Ara T, Nakahigashi K, Huang HC, Hirai A, Tsuzuki K, Nakamura S, Altaf-Ul-Amin M, Oshima T, Baba T, Yamamoto N, Kawamura T, Ioka-Nakamichi T, Kitagawa M, Tomita M, Kanaya S, Wada C, Mori H (2006). "Large-scale identification of protein-protein interaction of Escherichia coli K-12." Genome Res 16(5);686-91. PMID: 16606699

Badet87: Badet B, Vermoote P, Haumont PY, Lederer F, LeGoffic F (1987). "Glucosamine synthetase from Escherichia coli: purification, properties, and glutamine-utilizing site location." Biochemistry 1987;26(7);1940-8. PMID: 3297136

Badet88: Badet B, Vermoote P, Le Goffic F (1988). "Glucosamine synthetase from Escherichia coli: kinetic mechanism and inhibition by N3-fumaroyl-L-2,3-diaminopropionic derivatives." Biochemistry 1988;27(7);2282-7. PMID: 3132968

BadetDenisot92: Badet-Denisot MA, Badet B (1992). "Chemical modification of glucosamine-6-phosphate synthase by diethyl pyrocarbonate: evidence of histidine requirement for enzymatic activity." Arch Biochem Biophys 1992;292(2);475-8. PMID: 1731613

BadetDenisot95: Badet-Denisot MA, Leriche C, Massiere F, Badet B (1995). "Nitrogen transfer in E. coli glucosamine-6P synthase. Investigations using substrate and bisubstrate analogs." Bioorg. Med. Chem. Lett. 5(8);815-820.

Bairoch93: Bairoch A, Boeckmann B (1993). "The SWISS-PROT protein sequence data bank, recent developments." Nucleic Acids Res. 21:3093-3096. PMID: 8332529

Barreteau08: Barreteau H, Kovac A, Boniface A, Sova M, Gobec S, Blanot D (2008). "Cytoplasmic steps of peptidoglycan biosynthesis." FEMS Microbiol Rev 32(2);168-207. PMID: 18266853

Baveja86: Baveja UK, Jyoti AS, Kaur M, Agarwal DS, Anand BS, Nanda R (1986). "Isoenzyme studies of Giardia lamblia isolated from symptomatic cases." Aust J Exp Biol Med Sci 64 ( Pt 2);119-26. PMID: 2943257

Bearne00: Bearne SL, Blouin C (2000). "Inhibition of Escherichia coli glucosamine-6-phosphate synthase by reactive intermediate analogues. The role of the 2-amino function in catalysis." J Biol Chem 275(1);135-40. PMID: 10617596

Bearne95: Bearne SL, Wolfenden R (1995). "Glutamate gamma-semialdehyde as a natural transition state analogue inhibitor of Escherichia coli glucosamine-6-phosphate synthase." Biochemistry 34(36);11515-20. PMID: 7547881

Bearne96: Bearne SL (1996). "Active site-directed inactivation of Escherichia coli glucosamine-6-phosphate synthase. Determination of the fructose 6-phosphate binding constant using a carbohydrate-based inactivator." J Biol Chem 271(6);3052-7. PMID: 8621700

Bernstein65: Bernstein R, Robbins P "Control aspects of uridine 5'-diphosphate glucose and thymidine 5'-diphosphate glucose synthesis by microbial enzymes." J Biol Chem 1965;240(1):391-397.

Bertrand76: Bertrand O, Kahn A, Cottreau D, Boivin P (1976). "Human leukocyte glucose-phosphate-isomerase purification by affinity elution and immunological study." Biochimie 58(3);261-7. PMID: 819039

Blankenfeldt00: Blankenfeldt W, Giraud MF, Leonard G, Rahim R, Creuzenet C, Lam JS, Naismith JH (2000). "The purification, crystallization and preliminary structural characterization of glucose-1-phosphate thymidylyltransferase (RmlA), the first enzyme of the dTDP-L-rhamnose synthesis pathway from Pseudomonas aeruginosa." Acta Crystallogr D Biol Crystallogr 56(Pt 11);1501-4. PMID: 11053865

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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