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:||Biosynthesis → Cell Structures Biosynthesis → Lipopolysaccharide Biosynthesis → O-Antigen Biosynthesis|
Some taxa known to possess this pathway include : Escherichia coli K-12 substr. MG1655
Expected Taxonomic Range:
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.
Unification Links: EcoCyc:OANTIGEN-PWY
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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
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
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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
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.
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
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
Blankenfeldt02: Blankenfeldt W, Kerr ID, Giraud MF, McMiken HJ, Leonard G, Whitfield C, Messner P, Graninger M, Naismith JH (2002). "Variation on a theme of SDR. dTDP-6-deoxy-L- lyxo-4-hexulose reductase (RmlD) shows a new Mg2+-dependent dimerization mode." Structure 10(6);773-86. PMID: 12057193
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