Abstract
Bacterial lipopolysaccharide (LPS) is an important surface structure of Gramnegative bacteria for maintaining the integrity of the outer membrane. It is also a virulence factor in many bacteria, particularly those that are pathogens of plants and animals. Structurally, the LPS can be divided into three domains, lipid A, core oligosaccharide and O-polysaccharide (or O-antigen). Its polysaccharide constituents contain a great variety of sugars including neutral sugars, charged sugars that are acidic or amino substituted (see Chap. 3). Substitutions and enzymatic modifications of the basic sugar structure also lead to interesting deoxy or dideoxy sugars.
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Notes
- 1.
Numbers in parentheses refer to the corresponding structures depicted in the figures.
References
Varki A, Cummings R, Esko J, Freeze H, Hart G, Marth J (1999) Essentials of glycobiology. Cold Spring Harbor, New York
Thibodeaux CJ, Melancon CE III, Liu HW (2008) Natural-product sugar biosynthesis and enzymatic glycodiversification. Angew Chem Int Ed Engl 47:9814–9859
Leloir LF (1951) The enzymatic transformation of uridine diphosphate glucose into a galactose derivative. Arch Biochem 33:186–190
Lu M, Kleckner N (1994) Molecular cloning and characterization of the pgm gene encoding phosphoglucomutase of Escherichia coli. J Bacteriol 176:5847–5851
Coyne MJ Jr, Russell KS, Coyle CL, Goldberg JB (1994) The Pseudomonas aeruginosa algC gene encodes phosphoglucomutase, required for the synthesis of a complete lipopolysaccharide core. J Bacteriol 176:3500–3507
Kooistra O, Bedoux G, Brecker L, Lindner B, Sanchez Carballo P, Haras D, Zähringer U (2003) Structure of a highly phosphorylated lipopolysaccharide core in the Delta algC mutants derived from Pseudomonas aeruginosa wild-type strains PAO1 (serogroup O5) and PAC1R (serogroup O3). Carbohydr Res 338:2667–2677
Weissborn AC, Liu Q, Rumley MK, Kennedy EP (1994) UTP:α-d-glucose-1-phosphate uridylyltransferase of Escherichia coli: isolation and DNA sequence of the galU gene and purification of the enzyme. J Bacteriol 176:2611–2618
Thoden JB, Holden HM (2007) The molecular architecture of glucose-1-phosphate uridylyltransferase. Protein Sci 16:432–440
Priebe GP, Dean CR, Zaidi T, Meluleni GJ, Coleman FT, Coutinho YS, Noto MJ, Urban TA, Pier GB, Goldberg JB (2004) The galU gene of Pseudomonas aeruginosa is required for corneal infection and efficient systemic spread following pneumonia but not for infection confined to the lung. Infect Immun 72:4224–4232
Dean CR, Goldberg JB (2002) Pseudomonas aeruginosa galU is required for a complete lipopolysaccharide core and repairs a secondary mutation in a PA103 (serogroup O11) wbpM mutant. FEMS Microbiol Lett 210:277–283
Choudhury B, Carlson RW, Goldberg JB (2005) The structure of the lipopolysaccharide from a galU mutant of Pseudomonas aeruginosa serogroup-O11. Carbohydr Res 340:2761–2772
Mollerach M, Lopez R, Garcia E (1998) Characterization of the galU gene of Streptococcus pneumoniae encoding a uridine diphosphoglucose pyrophosphorylase: a gene essential for capsular polysaccharide biosynthesis. J Exp Med 188:2047–2056
Thoden JB, Holden HM (1998) Dramatic differences in the binding of UDP-galactose and UDP-glucose to UDP-galactose 4-epimerase from Escherichia coli. Biochemistry 37:11469–11477
Thoden JB, Frey PA, Holden HM (1996) Molecular structure of the NADH/UDP-glucose abortive complex of UDP-galactose 4-epimerase from Escherichia coli: implications for the catalytic mechanism. Biochemistry 35:5137–5144
Wilson DB, Hogness DS (1964) The enzymes of the galactose eperon in Escherichia coli. I. Purification and characterization of uridine diphosphogalactose 4-epimerase. J Biol Chem 239:2469–2481
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 178:4885–4893
Stenutz R, Weintraub A, Widmalm G (2006) The structures of Escherichia coli O-polysaccharide antigens. FEMS Microbiol Rev 30:382–403
Perepelov AV, Babicka D, Senchenkova SN, Shashkov AS, Moll H, Rozalski A, Zähringer U, Knirel YA (2001) Structure of the O-specific polysaccharide of Proteus vulgaris O4 containing a new component of bacterial polysaccharides, 4,6-dideoxy-4-{N-[(R)-3-hydroxybutyryl]-l-alanyl}amino-d-glucose. Carbohydr Res 331:195–202
Knirel YA, Paredes L, Jansson PE, Weintraub A, Widmalm G, Albert MJ (1995) Structure of the capsular polysaccharide of Vibrio cholerae O139 synonym Bengal containing d-galactose 4,6-cyclophosphate. Eur J Biochem 232:391–396
Munoz R, Mollerach M, Lopez R, Garcia E (1999) Characterization of the type 8 capsular gene cluster of Streptococcus pneumoniae. J Bacteriol 181:6214–6219
Lindberg B, Lindqvist B, Lönngren J, Powell DA (1980) Structural studies of the capsular polysaccharide from Streptococcus pneumoniae type 1. Carbohydr Res 78:111–117
Jansson PE, Lindberg B, Anderson M, Lindquist U, Henrichsen J (1988) Structural studies of the capsular polysaccharide from Streptococcus pneumoniae type 2, a reinvestigation. Carbohydr Res 182:111–117
Cartee RT, Forsee WT, Schutzbach JS, Yother J (2000) Mechanism of type 3 capsular polysaccharide synthesis in Streptococcus pneumoniae. J Biol Chem 275:3907–3914
Gottesman S, Stout V (1991) Regulation of capsular polysaccharide synthesis in Escherichia coli K12. Mol Microbiol 5:1599–1606
Arrecubieta C, Garcia E, Lopez R (1996) Demonstration of UDP-glucose dehydrogenase activity in cell extracts of Escherichia coli expressing the pneumococcal cap3A gene required for the synthesis of type 3 capsular polysaccharide. J Bacteriol 178:2971–2974
Jiang SM, Wang L, Reeves PR (2001) Molecular characterization of Streptococcus pneumoniae type 4, 6B, 8, and 18 C capsular polysaccharide gene clusters. Infect Immun 69:1244–1255
Hung RJ, Chien HS, Lin RZ, Lin CT, Vatsyayan J, Peng HL, Chang HY (2007) Comparative analysis of two UDP-glucose dehydrogenases in Pseudomonas aeruginosa PAO1. J Biol Chem 282:17738–17748
Loutet SA, Bartholdson SJ, Govan JR, Campopiano DJ, Valvano MA (2009) Contributions of two UDP-glucose dehydrogenases to viability and polymyxin B resistance of Burkholderia cenocepacia. Microbiology 155:2029–2039
Parolis H, Parolis LA (1995) The structure of the O-specific polysaccharide from Escherichia coli O113 lipopolysaccharide. Carbohydr Res 267:263–269
Hisatsune K, Kondo S, Isshiki Y, Iguchi T, Kawamata Y, Shimada T (1993) O-antigenic lipopolysaccharide of Vibrio cholerae O139 Bengal, a new epidemic strain for recent cholera in the Indian subcontinent. Biochem Biophys Res Commun 196:1309–1315
Isshiki Y, Kondo S, Iguchi T, Sano Y, Shimada T, Hisatsune K (1996) An immunochemical study of serological cross-reaction between lipopolysaccharides from Vibrio cholerae O22 and O139. Microbiology 142:1499–1504
Carlson RW, Garci F, Noel D, Hollingsworth R (1989) The structures of the lipopolysaccharide core components from Rhizobium leguminosarum biovar phaseoli CE3 and two of its symbiotic mutants, CE109 and CE309. Carbohydr Res 195:101–110
Vinogradov E, Sidorczyk Z, Knirel YA (2002) Structure of the core part of the lipopolysaccharides from Proteus penneri strains 7, 8, 14, 15, and 21. Carbohydr Res 337:643–649
Frirdich E, Bouwman C, Vinogradov E, Whitfield C (2005) The role of galacturonic acid in outer membrane stability in Klebsiella pneumoniae. J Biol Chem 280:27604–27612
Regue M, Hita B, Pique N, Izquierdo L, Merino S, Fresno S, Benedi VJ, Tomas JM (2004) A gene, uge, is essential for Klebsiella pneumoniae virulence. Infect Immun 72:54–61
Frirdich E, Whitfield C (2005) Characterization of Gla(KP), a UDP-galacturonic acid C4-epimerase from Klebsiella pneumoniae with extended substrate specificity. J Bacteriol 187:4104–4115
Reeves PR, Hobbs M, Valvano MA, Skurnik M, Whitfield C, Coplin D, Kido N, Klena J, Maskell D, Raetz CR, Rick PD (1996) Bacterial polysaccharide synthesis and gene nomenclature. Trends Microbiol 4:495–503
Erbing C, Svensson S, Hammarstrom S (1975) Structural studies on the O-specific side-chains of the cell-wall lipopolysaccharide from Escherichia coli O 75. Carbohydr Res 44:259–265
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 176:4144–4156
Knirel YA, Bystrova OV, Kocharova NA, Zähringer U, Pier GB (2006) Conserved and variable structural features in the lipopolysaccharide of Pseudomonas aeruginosa. J Endotoxin Res 12:324–336
Bystrova OV, Knirel YA, Lindner B, Kocharova NA, Kondakova AN, Zähringer U, Pier GB (2006) Structures of the core oligosaccharide and O-units in the R- and SR-type lipopolysaccharides of reference strains of Pseudomonas aeruginosa O-serogroups. FEMS Immunol Med Microbiol 46:85–99
Moreau M, Richards JC, Perry MB, Kniskern PJ (1988) Structural analysis of the specific capsular polysaccharide of Streptococcus pneumoniae type 45 (American type 72). Biochemistry 27:6820–6829
Daoust V, Carlo DJ, Zeltner JY, Perry MB (1981) Specific capsular polysaccharide of type 45 Streptococcus pneumoniae (American type 72). Infect Immun 32:1028–1033
Lutticken R, Temme N, Hahn G, Bartelheimer EW (1986) Meningitis caused by Streptococcus suis: case report and review of the literature. Infection 14:181–185
McNeil M, Daffe M, Brennan PJ (1990) Evidence for the nature of the link between the arabinogalactan and peptidoglycan of mycobacterial cell walls. J Biol Chem 265:18200–18206
Deng L, Mikusova K, Robuck KG, Scherman M, Brennan PJ, McNeil MR (1995) Recognition of multiple effects of ethambutol on metabolism of mycobacterial cell envelope. Antimicrob Agents Chemother 39:694–701
Blankenfeldt W, Asuncion M, Lam JS, Naismith JH (2000) The structural basis of the catalytic mechanism and regulation of glucose-1-phosphate thymidylyltransferase (RmlA). EMBO J 19:6652–6663
Shibaev VN (1986) Biosynthesis of bacterial polysaccharide chains composed of repeating units. Adv Carbohydr Chem Biochem 44:277–339
Koplin R, Wang G, Hotte B, Priefer UB, Puhler A (1993) A 3.9-kb DNA region of Xanthomonas campestris pv. campestris that is necessary for lipopolysaccharide production encodes a set of enzymes involved in the synthesis of dTDP-rhamnose. J Bacteriol 175:7786–7792
Melo A, Glaser L (1965) The nucleotide specificity and feedback control of thymidine diphosphate d-glucose pyrophosphorylase. J Biol Chem 240:398–405
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 56:1501–1504
Dong C, Major LL, Srikannathasan V, Errey JC, Giraud MF, Lam JS, Graninger M, Messner P, McNeil MR, Field RA, Whitfield C, Naismith JH (2007) RmlC, a C3′ and C5′ carbohydrate epimerase, appears to operate via an intermediate with an unusual twist boat conformation. J Mol Biol 365:146–159
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 307:283–295
Giraud MF, Leonard GA, Field RA, Berlind C, Naismith JH (2000) RmlC, the third enzyme of dTDP-l-rhamnose pathway, is a new class of epimerase. Nat Struct Biol 7:398–402
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 10:773–786
Li Q, Reeves PR (2000) Genetic variation of dTDP-l-rhamnose pathway genes in Salmonella enterica. Microbiology 146:2291–2307
Li Q, Hobbs M, Reeves PR (2003) The variation of dTDP-l-rhamnose pathway genes in Vibrio cholerae. Microbiology 149:2463–2474
Gaugler RW, Gabriel O (1973) Biological mechanisms involved in the formation of deoxy sugars. VII. Biosynthesis of 6-deoxy-l-talose. J Biol Chem 248:6041–6049
Jann B, Shashkov A, Torgov V, Kochanowski H, Seltmann G, Jann K (1995) NMR investigation of the 6-deoxy-l-talose-containing O45, O45-related (O45rel), and O66 polysaccharides of Escherichia coli. Carbohydr Res 278:155–165
Zähringer U, Rettenmaier H, Moll H, Senchenkova SN, Knirel YA (1997) Structure of a new 6-deoxy-α-d-talan from Burkholderia (Pseudomonas) plantarii strain DSM 6535, which is different from the O-chain of the lipopolysaccharide. Carbohydr Res 300:143–151
Russa R, Urbanik-Sypniewska T, Lindstrom K, Mayer H (1995) Chemical characterization of two lipopolysaccharide species isolated from Rhizobium loti NZP2213. Arch Microbiol 163:345–351
Shibuya N, Amano K, Azuma J, Nishihara T, Kitamura Y, Noguchi T, Koga T (1991) 6-Deoxy-d-talan and 6-deoxy-l-talan. Novel serotype-specific polysaccharide antigens from Actinobacillus actinomycetemcomitans. J Biol Chem 266:16318–16323
Nakano Y, Suzuki N, Yoshida Y, Nezu T, Yamashita Y, Koga T (2000) Thymidine diphosphate-6-deoxy-l-lyxo-4-hexulose reductase synthesizing dTDP-6-deoxy-l-talose from Actinobacillus actinomycetemcomitans. J Biol Chem 275:6806–6812
Senchenkova SN, Shashkov AS, Moran AP, Helander IM, Knirel YA (1995) Structures of the O-specific polysaccharide chains of Pectinatus cerevisiiphilus and Pectinatus frisingensis lipopolysaccharides. Eur J Biochem 232:552–557
Feng L, Senchenkova SN, Yang J, Shashkov AS, Tao J, Guo H, Cheng J, Ren Y, Knirel YA, Reeves PR, Wang L (2004) Synthesis of the heteropolysaccharide O antigen of Escherichia coli O52 requires an ABC transporter: structural and genetic evidence. J Bacteriol 186:4510–4519
Winn AM, Miles CT, Wilkinson SG (1996) Structure of the O3 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia. Carbohydr Res 282:149–156
Winn AM, Galbraith L, Temple GS, Wilkinson SG (1993) Structure of the O19 antigen of Xanthomonas maltophilia. Carbohydr Res 247:249–254
Knirel YA, Kochetkov NK (1994) The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens. Biochem Moscow 12:1325–1383
Amano K, Nishihara T, Shibuya N, Noguchi T, Koga T (1989) Immunochemical and structural characterization of a serotype-specific polysaccharide antigen from Actinobacillus actinomycetemcomitans Y4 (serotype b). Infect Immun 57:2942–2946
Kählig H, Kolarich D, Zayni S, Scheberl A, Kosma P, Schäffer C, Messner P (2005) N-Acetylmuramic acid as capping element of a-d-fucose-containing S-layer glycoprotein glycans from Geobacillus tepidamans GS5-97T. J Biol Chem 280:20292–20299
Yoshida Y, Nakano Y, Nezu T, Yamashita Y, Koga T (1999) A novel NDP-6-deoxyhexosyl-4-ulose reductase in the pathway for the synthesis of thymidine diphosphate-d-fucose. J Biol Chem 274:16933–16939
Wang Q, Ding P, Perepelov AV, Xu Y, Wang Y, Knirel YA, Wang L, Feng L (2008) Characterization of the dTDP-d-fucofuranose biosynthetic pathway in Escherichia coli O52. Mol Microbiol 70:1358–1367
Knirel YA, Dashunin VV, Shashkov AS, Kochetkov NK, Dmitriev BA, Hofman IL (1988) Somatic antigens of Shigella: structure of the O-specific polysaccharide chain of the Shigella dysenteriae type 7 lipopolysaccharide. Carbohydr Res 179:51–60
Parolis H, Parolis LA, Olivieri G (1997) Structural studies on the Shigella-like Escherichia coli O121 O-specific polysaccharide. Carbohydr Res 303:319–325
L’vov VL, Shashkov AS, Dmitriev BA, Kochetkov NK, Jann B, Jann K (1984) Structural studies of the O-specific side chain of the lipopolysaccharide from Escherichia coli O:7. Carbohydr Res 126:249–259
Wang Y, Xu Y, Perepelov AV, Qi Y, Knirel YA, Wang L, Feng L (2007) Biochemical characterization of dTDP-d-Qui4N and dTDP-d-Qui4NAc biosynthetic pathways in Shigella dysenteriae type 7 and Escherichia coli O7. J Bacteriol 189:8626–8635
Lüderitz O, Staub AM, Westphal O (1966) Immunochemistry of O and R antigens of Salmonella and related Enterobacteriaceae. Bacteriol Rev 30:192–255
Jansson PE, Lönngren J, Widmalm G, Leontein K, Slettengren K, Svenson SB, Wrangsell G, Dell A, Tiller PR (1985) Structural studies of the O-antigen polysaccharides of Klebsiella O5 and Escherichia coli O8. Carbohydr Res 145:59–66
Ørskov I, Ørskov F (1984) Serotyping of Klebsiella. In: Bergan T (ed) Methods in microbiology, vol 14. Academic, London, pp 143–164
Prehm P, Jann B, Jann K (1976) The O9 antigen of Escherichia coli. Structure of the polysaccharide chain. Eur J Biochem 67:53–56
Kuhlman M, Joiner K, Ezekowitz RA (1989) The human mannose-binding protein functions as an opsonin. J Exp Med 169:1733–1745
Sahly H, Ofek I, Podschun R, Brade H, He Y, Ullmann U, Crouch E (2002) Surfactant protein D binds selectively to Klebsiella pneumoniae lipopolysaccharides containing mannose-rich O-antigens. J Immunol 169:3267–3274
Neidhardt FC, Curtiss R III, Ingraham JL, Lin ECC, Low BK, Magasanik B, Reznikoff WS, Riley M, Schaechter M, Umbarger HE (eds) (1996) Escherichia coli and Salmonella: cellular and molecular biology, 2nd edn. ASM Press, Washington, DC
Rocchetta HL, Pacan JC, Lam JS (1998) Synthesis of the A-band polysaccharide sugar d-rhamnose requires Rmd and WbpW: identification of multiple AlgA homologues, WbpW and ORF488, in Pseudomonas aeruginosa. Mol Microbiol 29:1419–1434
Jensen SO, Reeves PR (2001) Molecular evolution of the GDP-mannose pathway genes (manB and manC) in Salmonella enterica. Microbiology 147:599–610
Byrd MS, Sadovskaya I, Vinogradov E, Lu H, Sprinkle AB, Richardson SH, Ma L, Ralston B, Parsek MR, Anderson EM, Lam JS, Wozniak DJ (2009) Genetic and biochemical analyses of the Pseudomonas aeruginosa Psl exopolysaccharide reveal overlapping roles for polysaccharide synthesis enzymes in Psl and LPS production. Mol Microbiol 73:622–638
Shinabarger D, Berry A, May TB, Rothmel R, Fialho A, Chakrabarty AM (1991) Purification and characterization of phosphomannose isomerase-guanosine diphospho-d-mannose pyrophosphorylase. A bifunctional enzyme in the alginate biosynthetic pathway of Pseudomonas aeruginosa. J Biol Chem 266:2080–2088
Lee HJ, Chang HY, Venkatesan N, Peng HL (2008) Identification of amino acid residues important for the phosphomannose isomerase activity of PslB in Pseudomonas aeruginosa PAO1. FEBS Lett 582:3479–3483
Mulichak AM, Bonin CP, Reiter WD, Garavito RM (2002) Structure of the MUR1 GDP-mannose 4,6-dehydratase from Arabidopsis thaliana: implications for ligand binding and specificity. Biochemistry 41:15578–15589
Somoza JR, Menon S, Schmidt H, Joseph-McCarthy D, Dessen A, Stahl ML, Somers WS, Sullivan FX (2000) Structural and kinetic analysis of Escherichia coli GDP-mannose 4,6 dehydratase provides insights into the enzyme’s catalytic mechanism and regulation by GDP-fucose. Structure 8:123–135
Webb NA, Mulichak AM, Lam JS, Rocchetta HL, Garavito RM (2004) Crystal structure of a tetrameric GDP-d-mannose 4,6-dehydratase from a bacterial GDP-d-rhamnose biosynthetic pathway. Protein Sci 13:529–539
Arsenault TL, Hughes DW, MacLean DB, Szarek WA, Kropinski AMB, Lam JS (1991) Structural studies on the polysaccharide portion of “A-band” lipopolysaccharide from a mutant (AK1401) of Pseudomonas aeruginosa strain PAO1. Can J Chem 69:1273–1280
Yokota S, Kaya S, Sawada S, Kawamura T, Araki Y, Ito E (1987) Characterization of a polysaccharide component of lipopolysaccharide from Pseudomonas aeruginosa IID 1008 (ATCC 27584) as d-rhamnan. Eur J Biochem 167:203–209
Ovod V, Rudolph K, Knirel Y, Krohn K (1996) Immunochemical characterization of O polysaccharides composing the α-d-rhamnose backbone of lipopolysaccharide of Pseudomonas syringae and classification of bacteria into serogroups O1 and O2 with monoclonal antibodies. J Bacteriol 178:6459–6465
Molinaro A, Silipo A, Lanzetta R, Newman MA, Dow JM, Parrilli M (2003) Structural elucidation of the O-chain of the lipopolysaccharide from Xanthomonas campestris strain 8004. Carbohydr Res 338:277–281
Senchenkova SN, Shashkov AS, Knirel YA, McGovern JJ, Moran AP (1996) The O-specific polysaccharide chain of Campylobacter fetus serotype B lipopolysaccharide is a d-rhamnan terminated with 3-O-methyl-d-rhamnose (d-acofriose). Eur J Biochem 239:434–438
Kocharova NA, Knirel YA, Widmalm G, Jansson PE, Moran AP (2000) Structure of an atypical O-antigen polysaccharide of Helicobacter pylori containing a novel monosaccharide 3-C-methyl-d-mannose. Biochemistry 39:4755–4760
Kneidinger B, Graninger M, Adam G, Puchberger M, Kosma P, Zayni S, Messner P (2001) Identification of two GDP-6-deoxy-d- lyxo-4-hexulose reductases synthesizing GDP-d-rhamnose in Aneurinibacillus thermoaerophilus L420-91T. J Biol Chem 276:5577–5583
King JD, Poon KK, Webb NA, Anderson EM, McNally DJ, Brisson JR, Messner P, Garavito RM, Lam JS (2009) The structural basis for catalytic function of GMD and RMD, two closely related enzymes from the GDP-d-rhamnose biosynthesis pathway. FEBS J 276:2686–2700
Maki M, Jarvinen N, Rabina J, Roos C, Maaheimo H, Renkonen R (2002) Functional expression of Pseudomonas aeruginosa GDP-6-deoxy-4-keto-d-mannose reductase which synthesizes GDP-rhamnose. Eur J Biochem 269:593–601
Perry MB, MacLean LM, Brisson JR, Wilson ME (1996) Structures of the antigenic O-polysaccharides of lipopolysaccharides produced by Actinobacillus actinomycetemcomitans serotypes a, c, d and e. Eur J Biochem 242:682–688
Maki M, Jarvinen N, Rabina J, Maaheimo H, Mattila P, Renkonen R (2003) Cloning and functional expression of a novel GDP-6-deoxy-d-talose synthetase from Actinobacillus actinomycetemcomitans. Glycobiology 13:295–303
Suzuki N, Nakano Y, Yoshida Y, Nezu T, Terada Y, Yamashita Y, Koga T (2002) Guanosine diphosphate-6-deoxy-4-keto-d-mannose reductase in the pathway for the synthesis of GDP-6-deoxy-d-talose in Actinobacillus actinomycetemcomitans. Eur J Biochem 269:5963–5971
Tonetti M, Sturla L, Bisso A, Zanardi D, Benatti U, De Flora A (1998) The metabolism of 6-deoxyhexoses in bacterial and animal cells. Biochimie 80:923–931
Becker DJ, Lowe JB (2003) Fucose: biosynthesis and biological function in mammals. Glycobiology 13:41R–53R
Whitfield C, Roberts IS (1999) Structure, assembly and regulation of expression of capsules in Escherichia coli. Mol Microbiol 31:1307–1319
Carlson RW, Price NP, Stacey G (1994) The biosynthesis of rhizobial lipo-oligosaccharide nodulation signal molecules. Mol Plant Microbe Interact 7:684–695
Stacey G, Luka S, Sanjuan J, Banfalvi Z, Nieuwkoop AJ, Chun JY, Forsberg LS, Carlson R (1994) nodZ, a unique host-specific nodulation gene, is involved in the fucosylation of the lipooligosaccharide nodulation signal of Bradyrhizobium japonicum. J Bacteriol 176:620–633
Wang L, Reeves PR (1998) Organization of Escherichia coli O157 O antigen gene cluster and identification of its specific genes. Infect Immun 66:3545–3551
Zhang L, Radziejewska-Lebrecht J, Krajewska-Pietrasik D, Toivanen P, Skurnik M (1997) Molecular and chemical characterization of the lipopolysaccharide O-antigen and its role in the virulence of Yersinia enterocolitica serotype O:8. Mol Microbiol 23:63–76
Skurnik M, Zhang L (1996) Molecular genetics and biochemistry of Yersinia lipopolysaccharide. APMIS 104:849–872
Moran AP, O’Malley DT, Kosunen TU, Helander IM (1994) Biochemical characterization of Campylobacter fetus lipopolysaccharides. Infect Immun 62:3922–3929
Wang G, Ge Z, Rasko DA, Taylor DE (2000) Lewis antigens in Helicobacter pylori: biosynthesis and phase variation. Mol Microbiol 36:1187–1196
Appelmelk BJ, Vandenbroucke-Grauls CM (2000) H. pylori and Lewis antigens. Gut 47:10–11
Andrianopoulos K, Wang L, Reeves PR (1998) Identification of the fucose synthetase gene in the colanic acid gene cluster of Escherichia coli K-12. J Bacteriol 180:998–1001
Rosano C, Bisso A, Izzo G, Tonetti M, Sturla L, De Flora A, Bolognesi M (2000) Probing the catalytic mechanism of GDP-6-deoxy-4-keto-d-mannose epimerase/reductase by kinetic and crystallographic characterization of site-specific mutants. J Mol Biol 303:77–91
Wu B, Zhang Y, Wang PG (2001) Identification and characterization of GDP-d-mannose 4,6-dehydratase and GDP-l-fucose snthetase in a GDP-l-fucose biosynthetic gene cluster from Helicobacter pylori. Biochem Biophys Res Commun 285:364–371
Xiang SH, Haase AM, Reeves PR (1993) Variation of the rfb gene clusters in Salmonella enterica. J Bacteriol 175:4877–4884
Edstrom RD, Heath EC (1965) Isolation of colitose-containing oligosaccharides from the cell wall lipopolysaccharide of Escherichia coli. Biochem Biophys Res Commun 21:638–643
Lindberg B, Lindh F, Lönngren J (1981) Structural studies of the O-specific side-chain of the lipopolysaccharide from Escherichia coli O 55. Carbohydr Res 97:105–112
Cox AD, Brisson JR, Varma V, Perry M (1996) Structural analysis of the lipopolysaccharide from Vibrio cholerae O139. Carbohydr Res 290:43–58
Komandrova NA, Gorshkova RP, Zubkov VA, Ovodov IuS (1989) The structure of the O-specific polysaccharide chain of the lipopolysaccharide of Yersinia pseudotuberculosis serovar VII. Bioorg Khim 15:104–110
Muldoon J, Perepelov AV, Shashkov AS, Gorshkova RP, Nazarenko EL, Zubkov VA, Ivanova EP, Knirel YA, Savage AV (2001) Structure of a colitose-containing O-specific polysaccharide of the marine bacterium Pseudoalteromonas tetraodonis IAM 14160T. Carbohydr Res 333:41–46
Silipo A, Molinaro A, Nazarenko EL, Gorshkova RP, Ivanova EP, Lanzetta R, Parrilli M (2005) The O-chain structure from the LPS of marine halophilic bacterium Pseudoalteromonas carrageenovora-type strain IAM 12662T. Carbohydr Res 340:2693–2697
Elbein AD, Heath EC (1965) The biosynthesis of cell wall lipopolysaccharide in Escherichia coli. II. Guanosine diphosphate C-6-deoxy-4-keto-d-mannose, an intermediate in the biosynthesis of guanosine diphosphate colitose. J Biol Chem 240:1926–1931
Cook PD, Holden HM (2008) GDP-6-deoxy-4-keto-d-mannose 3-dehydratase, accommodating a sugar substrate in the active site. J Biol Chem 283:4295–4303
Beyer N, Alam J, Hallis TM, Guo Z, Liu HW (2003) The biosynthesis of GDP-l-colitose: C-3 deoxygenation is catalyzed by a unique coenzyme B6-dependent enzyme. J Am Chem Soc 125:5584–5585
Alam J, Beyer N, Liu HW (2004) Biosynthesis of colitose: expression, purification, and mechanistic characterization of GDP-6-deoxy-4-keto-d-mannose-3-dehydrase (ColD) and GDP-l-colitose synthase (ColC). Biochemistry 43:16450–16460
Cook PD, Thoden JB, Holden HM (2006) The structure of GDP-6-deoxy-4-keto-d-mannose-3-dehydratase: a unique coenzyme B6-dependent enzyme. Protein Sci 15:2093–2106
Cook PD, Holden HM (2007) A structural study of GDP-6-deoxy-4-keto-d-mannose-3-dehydratase: caught in the act of geminal diamine formation. Biochemistry 46:14215–14224
Redmond JW (1975) 4-Amino-4,6-dideoxy-d-mannose (d-perosamine): a component of the lipopolysaccharide of Vibrio cholerae 569B (Inaba). FEBS Lett 50:147–149
Awram P, Smit J (2001) Identification of lipopolysaccharide O antigen synthesis genes required for attachment of the S-layer of Caulobacter crescentus. Microbiology 147:1451–1460
Perry MB, MacLean L, Griffith DW (1986) Structure of the O-chain polysaccharide of the phenol-phase soluble lipopolysaccharide of Escherichia coli O:157:H7. Biochem Cell Biol 64:21–28
Samuel G, Hogbin JP, Wang L, Reeves PR (2004) Relationships of the Escherichia coli O157, O111, and O55 O-antigen gene clusters with those of Salmonella enterica and Citrobacter freundii, which express identical O antigens. J Bacteriol 186:6536–6543
Bettelheim KA, Evangelidis H, Pearce JL, Sowers E, Strockbine NA (1993) Isolation of a Citrobacter freundii strain which carries the Escherichia coli O157 antigen. J Clin Microbiol 31:760–761
Stroeher UH, Karageorgos LE, Brown MH, Morona R, Manning PA (1995) A putative pathway for perosamine biosynthesis is the first function encoded within the rfb region of Vibrio cholerae O1. Gene 166:33–42
Albermann C, Piepersberg W (2001) Expression and identification of the RfbE protein from Vibrio cholerae O1 and its use for the enzymatic synthesis of GDP-d-perosamine. Glycobiology 11:655–661
Zhao G, Liu J, Liu X, Chen M, Zhang H, Wang PG (2007) Cloning and characterization of GDP-perosamine synthetase (Per) from Escherichia coli O157:H7 and synthesis of GDP-perosamine in vitro. Biochem Biophys Res Commun 363:525–530
Cook PD, Holden HM (2008) GDP-perosamine synthase: structural analysis and production of a novel trideoxysugar. Biochemistry 47:2833–2840
Cook PD, Kubiak RL, Toomey DP, Holden HM (2009) Two site-directed mutations are required for the conversion of a sugar dehydratase into an aminotransferase. Biochemistry 48:5246–5253
Albermann C, Beuttler H (2008) Identification of the GDP-N-acetyl-d-perosamine producing enzymes from Escherichia coli O157:H7. FEBS Lett 582:479–484
Raetz CR (1987) Structure and biosynthesis of lipid A. In: Neidhardt FC, Ingraham JL, Low KB, Magasanik B, Schaechter M, Umbarger HE (eds) Escherichia coli and Salmonella typhimurium: cellular and molecular biology, vol 1. ASM Press, Washington, DC, pp 498–503
Kuhn HM, Meier-Dieter U, Mayer H (1988) ECA, the enterobacterial common antigen. FEMS Microbiol Rev 4:195–222
Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Wang Q, Reeves PR, Wang L (2008) Structure and genetics of Shigella O antigens. FEMS Microbiol Rev 32:627–653
Knirel YA, Perepelov AV, Kondakova AN, Senchenkova SN, Sidorczyk Z, Rozalski A, Kaca W (2011) Structure and serology of O-antigens as the basis for classification of Proteus strains. Innate Immun 17:70–96
Park JT (1987) Murein synthesis. In: Neidhardt FC, Ingraham JL, Low KB, Magasanik B, Schaechter M, Umbarger HE (eds) Escherichia coli and Salmonella typhimurium: cellular and molecular biology, vol 1. ASM Press, Washington, DC, pp 663–671
Holtje JV, Schwarz U (1985) Biosynthesis and growth of the murein sacculus. In: Nanninga N (ed) Molecular cytology of Escherichia coli. Academic, London, pp 77–119
Dutka-Malen S, Mazodier P, Badet B (1988) Molecular cloning and overexpression of the glucosamine synthetase gene from Escherichia coli. Biochimie 70:287–290
Mengin-Lecreulx D, van Heijenoort J (1996) Characterization of the essential gene glmM encoding phosphoglucosamine mutase in Escherichia coli. J Biol Chem 271:32–39
Mengin-Lecreulx D, van Heijenoort J (1993) Identification of the glmU gene encoding N-acetylglucosamine-1-phosphate uridyltransferase in Escherichia coli. J Bacteriol 175:6150–6157
Mengin-Lecreulx D, van Heijenoort J (1994) Copurification of glucosamine-1-phosphate acetyltransferase and N-acetylglucosamine-1-phosphate uridyltransferase activities of Escherichia coli: characterization of the glmU gene product as a bifunctional enzyme catalyzing two subsequent steps in the pathway for UDP-N-acetylglucosamine synthesis. J 7Bacteriol 176:5788–5795
Sarvas M (1971) Mutant of Escherichia coli K-12 defective in d-glucosamine biosynthesis. J Bacteriol 105:467–471
Wu HC, Wu TC (1971) Isolation and characterization of a glucosamine-requiring mutant of Escherichia coli K-12 defective in glucosamine-6-phosphate synthetase. J Bacteriol 105:455–466
Green DW (2002) The bacterial cell wall as a source of antibacterial targets. Expert Opin Ther Targets 6:1–19
Jolly L, Ferrari P, Blanot D, Van Heijenoort J, Fassy F, Mengin-Lecreulx D (1999) Reaction mechanism of phosphoglucosamine mutase from Escherichia coli. Eur J Biochem 262:202–210
Jolly L, Pompeo F, van Heijenoort J, Fassy F, Mengin-Lecreulx D (2000) Autophosphorylation of phosphoglucosamine mutase from Escherichia coli. J Bacteriol 182:1280–1285
Segel IH (1975) Enzyme kinetics, behavior and analysis of rapid equilibrium and steady state enzyme systems. Wiley, New York
De Reuse H, Labigne A, Mengin-Lecreulx D (1997) The Helicobacter pylori ureC gene codes for a phosphoglucosamine mutase. J Bacteriol 179:3488–3493
Tavares IM, Jolly L, Pompeo F, Leitao JH, Fialho AM, Sa-Correia I, Mengin-Lecreulx D (2000) Identification of the Pseudomonas aeruginosa glmM gene, encoding phosphoglucosamine mutase. J Bacteriol 182:4453–4457
Shimazu K, Takahashi Y, Uchikawa Y, Shimazu Y, Yajima A, Takashima E, Aoba T, Konishi K (2008) Identification of the Streptococcus gordonii glmM gene encoding phosphoglucosamine mutase and its role in bacterial cell morphology, biofilm formation, and sensitivity to antibiotics. FEMS Immunol Med Microbiol 53:166–177
Jolly L, Wu S, van Heijenoort J, de Lencastre H, Mengin-Lecreulx D, Tomasz A (1997) The femR315 gene from Staphylococcus aureus, the interruption of which results in reduced methicillin resistance, encodes a phosphoglucosamine mutase. J Bacteriol 179:5321–5325
Verma SK, Jaiswal M, Kumar N, Parikh A, Nandicoori VK, Prakash B (2009) Structure of N-acetylglucosamine-1-phosphate uridyltransferase (GlmU) from Mycobacterium tuberculosis in a cubic space group. Acta Crystallogr F Struct Biol Cryst Commun 65:435–439
Zhang Z, Bulloch EM, Bunker RD, Baker EN, Squire CJ (2009) Structure and function of GlmU from Mycobacterium tuberculosis. Acta Crystallogr D Biol Crystallogr 65:275–283
Olsen LR, Roderick SL (2001) Structure of the Escherichia coli GlmU pyrophosphorylase and acetyltransferase active sites. Biochemistry 40:1913–1921
Gehring AM, Lees WJ, Mindiola DJ, Walsh CT, Brown ED (1996) Acetyltransfer precedes uridylyltransfer in the formation of UDP-N-acetylglucosamine in separable active sites of the bifunctional GlmU protein of Escherichia coli. Biochemistry 35:579–585
Olsen LR, Vetting MW, Roderick SL (2007) Structure of the E. coli bifunctional GlmU acetyltransferase active site with substrates and products. Protein Sci 16:1230–1235
Brown K, Pompeo F, Dixon S, Mengin-Lecreulx D, Cambillau C, Bourne Y (1999) Crystal structure of the bifunctional N-acetylglucosamine 1-phosphate uridyltransferase from Escherichia coli: a paradigm for the related pyrophosphorylase superfamily. EMBO J 18:4096–4107
Kostrewa D, D’Arcy A, Takacs B, Kamber M (2001) Crystal structures of Streptococcus pneumoniae N-acetylglucosamine-1-phosphate uridyltransferase, GlmU, in apo form at 2.33 Å resolution and in complex with UDP-N-acetylglucosamine and Mg2+ at 1.96 Å resolution. J Mol Biol 305:279–289
Mochalkin I, Lightle S, Zhu Y, Ohren JF, Spessard C, Chirgadze NY, Banotai C, Melnick M, McDowell L (2007) Characterization of substrate binding and catalysis in the potential antibacterial target N-acetylglucosamine-1-phosphate uridyltransferase (GlmU). Protein Sci 16:2657–2666
King JD, Kocincova D, Westman EL, Lam JS (2009) Lipopolysaccharide biosynthesis in Pseudomonas aeruginosa. Innate Immun 15:261–312
Bhat UR, Krishnaiah BS, Carlson RW (1991) Re-examination of the structures of the lipopolysaccharide core oligosaccharides from Rhizobium leguminosarum biovar phaseoli. Carbohydr Res 220:219–227
Forsberg LS, Carlson RW (1998) The structures of the lipopolysaccharides from Rhizobium etli strains CE358 and CE359. The complete structure of the core region of R. etli lipopolysaccharides. J Biol Chem 273:2747–2757
Creuzenet C, Lam JS (2001) Topological and functional characterization of WbpM, an inner membrane UDP-GlcNAc C6 dehydratase essential for lipopolysaccharide biosynthesis in Pseudomonas aeruginosa. Mol Microbiol 41:1295–1310
DiGiandomenico A, Matewish MJ, Bisaillon A, Stehle JR, Lam JS, Castric P (2002) Glycosylation of Pseudomonas aeruginosa 1244 pilin: glycan substrate specificity. Mol Microbiol 46:519–530
Burrows LL, Urbanic RV, Lam JS (2000) Functional conservation of the polysaccharide biosynthetic protein WbpM and its homologues in Pseudomonas aeruginosa and other medically significant bacteria. Infect Immun 68:931–936
Burrows LL, Charter DF, Lam JS (1996) Molecular characterization of the Pseudomonas aeruginosa serotype O5 (PAO1) B-band lipopolysaccharide gene cluster. Mol Microbiol 22:481–495
Belanger M, Burrows LL, Lam JS (1999) Functional analysis of genes responsible for the synthesis of the B-band O antigen of Pseudomonas aeruginosa serotype O6 lipopolysaccharide. Microbiology 145:3505–3521
Schoenhofen IC, McNally DJ, Vinogradov E, Whitfield D, Young NM, Dick S, Wakarchuk WW, Brisson JR, Logan SM (2006) Functional characterization of dehydratase/aminotransferase pairs from Helicobacter and Campylobacter: enzymes distinguishing the pseudaminic acid and bacillosamine biosynthetic pathways. J Biol Chem 281:723–732
Pinta E, Duda KA, Hanuszkiewicz A, Kaczynski Z, Lindner B, Miller WL, Hyytiainen H, Vogel C, Borowski S, Kasperkiewicz K, Lam JS, Radziejewska-Lebrecht J, Skurnik M, Holst O (2009) Identification and role of a 6-deoxy-4-keto-hexosamine in the lipopolysaccharide outer core of Yersinia enterocolitica serotype O:3. Chem Eur J 15:9747–9754
Forsberg LS, Noel KD, Box J, Carlson RW (2003) Genetic locus and structural characterization of the biochemical defect in the O-antigenic polysaccharide of the symbiotically deficient Rhizobium etli mutant, CE166. Replacement of N-acetylquinovosamine with its hexosyl-4-ulose precursor. J Biol Chem 278:51347–51359
Miller WL, Lam JS (2007) Molecular biology of cell-surface polysaccharides in Pseudomonas aeruginosa: from gene to protein function. In: Cornelis P (ed) Pseudomonas: genomics and molecular biology. Horizon Scientific Press, Norfolk, pp 87–128
Radziejewska-Lebrecht J, Skurnik M, Shashkov AS, Brade L, Rozalski A, Bartodziejska B, Mayer H (1998) Immunochemical studies on R mutants of Yersinia enterocolitica O:3. Acta Biochim Pol 45:1011–1019
Sadovskaya I, Brisson JR, Khieu NH, Mutharia LM, Altman E (1998) Structural characterization of the lipopolysaccharide O-antigen and capsular polysaccharide of Vibrio ordalii serotype O:2. Eur J Biochem 253:319–327
MacLean LL, Perry MB, Crump EM, Kay WW (2003) Structural characterization of the lipopolysaccharide O-polysaccharide antigen produced by Flavobacterium columnare ATCC 43622. Eur J Biochem 270:3440–3446
Kilcoyne M, Shashkov AS, Knirel YA, Gorshkova RP, Nazarenko EL, Ivanova EP, Gorshkova NM, Senchenkova SN, Savage AV (2005) The structure of the O-polysaccharide of the Pseudoalteromonas rubra ATCC 29570T lipopolysaccharide containing a keto sugar. Carbohydr Res 340:2369–2375
Jansson PE, Lindberg B, Lindquist U (1985) Structural studies of the capsular polysaccharide from Streptococcus pneumoniae type 5. Carbohydr Res 140:101–110
Marsden BJ, Bundle DR, Perry MB (1994) Serological and structural relationships between Escherichia coli O:98 and Yersinia enterocolitica O:11,23 and O:11,24 lipopolysaccharide O-antigens. Biochem Cell Biol 72:163–168
Feng L, Senchenkova SN, Yang J, Shashkov AS, Tao J, Guo H, Zhao G, Knirel YA, Reeves P, Wang L (2004) Structural and genetic characterization of the Shigella boydii type 13 O antigen. J Bacteriol 186:383–392
Perepelov AV, Liu B, Senchenkova SN, Shashkov AS, Feng L, Knirel YA, Wang L (2010) Structure of the O-polysaccharide of Salmonella enterica O41. Carbohydr Res 345:971–973
Kasper DL, Weintraub A, Lindberg AA, Lönngren J (1983) Capsular polysaccharides and lipopolysaccharides from two Bacteroides fragilis reference strains: chemical and immunochemical characterization. J Bacteriol 153:991–997
Kneidinger B, O’Riordan K, Li J, Brisson JR, Lee JC, Lam JS (2003) Three highly conserved proteins catalyze the conversion of UDP-N-acetyl-d-glucosamine to precursors for the biosynthesis of O antigen in Pseudomonas aeruginosa O11 and capsule in Staphylococcus aureus type 5. Implications for the UDP-N-acetyl-l-fucosamine biosynthetic pathway. J Biol Chem 278:3615–3627
Vinogradov EV, Knirel’ Iu A, Lipkind GM, Shashkov AS, Kochetkov NK (1987) Antigenic bacterial polysaccharides. 23. The structure of the O-specific polysaccharide chain of Salmonella arizonae O59 lipopolysaccharide. Bioorg Khim 13:1275–1281
Moreau M, Richards JC, Fournier JM, Byrd RA, Karakawa WW, Vann WF (1990) Structure of the type 5 capsular polysaccharide of Staphylococcus aureus. Carbohydr Res 201:285–297
Fournier JM, Vann WF, Karakawa WW (1984) Purification and characterization of Staphylococcus aureus type 8 capsular polysaccharide. Infect Immun 45:87–93
Jones C, Currie F, Forster MJ (1991) N.m.r. and conformational analysis of the capsular polysaccharide from Streptococcus pneumoniae type 4. Carbohydr Res 221:95–121
Mulrooney EF, Poon KK, McNally DJ, Brisson JR, Lam JS (2005) Biosynthesis of UDP-N-acetyl-l-fucosamine, a precursor to the biosynthesis of lipopolysaccharide in Pseudomonas aeruginosa serotype O11. J Biol Chem 280:19535–19542
Kneidinger B, Larocque S, Brisson JR, Cadotte N, Lam JS (2003) Biosynthesis of 2-acetamido-2,6-dideoxy-l-hexoses in bacteria follows a pattern distinct from those of the pathways of 6-deoxy-l-hexoses. Biochem J 371:989–995
McNally DJ, Schoenhofen IC, Mulrooney EF, Whitfield DM, Vinogradov E, Lam JS, Logan SM, Brisson JR (2006) Identification of labile UDP-ketosugars in Helicobacter pylori, Campylobacter jejuni and Pseudomonas aeruginosa: key metabolites used to make glycan virulence factors. Chembiochem 7:1865–1868
Ishiyama N, Creuzenet C, Miller WL, Demendi M, Anderson EM, Harauz G, Lam JS, Berghuis AM (2006) Structural studies of FlaA1 from Helicobacter pylori reveal the mechanism for inverting 4,6-dehydratase activity. J Biol Chem 281:24489–24495
Morrison JP, Schoenhofen IC, Tanner ME (2008) Mechanistic studies on PseB of pseudaminic acid biosynthesis: a UDP-N-acetylglucosamine 5-inverting 4,6-dehydratase. Bioorg Chem 36:312–320
Bystrova OV, Lindner B, Moll H, Kocharova NA, Knirel YA, Zähringer U, Pier GB (2003) Structure of the lipopolysaccharide of Pseudomonas aeruginosa O-12 with a randomly O-acetylated core region. Carbohydr Res 338:1895–1905
Feng L, Senchenkova SN, Tao J, Shashkov AS, Liu B, Shevelev SD, Reeves PR, Xu J, Knirel YA, Wang L (2005) Structural and genetic characterization of enterohemorrhagic Escherichia coli O145 O antigen and development of an O145 serogroup-specific PCR assay. J Bacteriol 187:758–764
Gamian A, Jones C, Lipinski T, Korzeniowska-Kowal A, Ravenscroft N (2000) Structure of the sialic acid-containing O-specific polysaccharide from Salmonella enterica serovar Toucra O48 lipopolysaccharide. Eur J Biochem 267:3160–3167
King JD, Mulrooney EF, Vinogradov E, Kneidinger B, Mead K, Lam JS (2008) lfnA from Pseudomonas aeruginosa O12 and wbuX from Escherichia coli O145 encode membrane-associated proteins and are required for expression of 2,6-dideoxy-2-acetamidino-l-galactose in lipopolysaccharide O antigen. J Bacteriol 190:1671–1679
Baumann H, Jansson PE, Kenne L, Widmalm G (1991) Structural studies of the Escherichia coli O1A O-polysaccharide, using the computer program CASPER. Carbohydr Res 211:183–190
Gupta DS, Shashkov AS, Jann B, Jann K (1992) Structures of the O1B and O1C lipopolysaccharide antigens of Escherichia coli. J Bacteriol 174:7963–7970
Perry MB, MacLean LL, Brisson JR (1993) The characterization of the O-antigen of Escherichia coli O64:K99 lipopolysaccharide. Carbohydr Res 248:277–284
Wang Z, Vinogradov E, Larocque S, Harrison BA, Li J, Altman E (2005) Structural and serological characterization of the O-chain polysaccharide of Aeromonas salmonicida strains A449, 80204 and 80204-1. Carbohydr Res 340:693–700
Keenleyside WJ, Perry M, Maclean L, Poppe C, Whitfield C (1994) A plasmid-encoded rfbO:54 gene cluster is required for biosynthesis of the O:54 antigen in Salmonella enterica serovar Borreze. Mol Microbiol 11:437–448
Mäkela PH, Mayer H (1976) Enterobacterial common antigen. Bacteriol Rev 40:591–632
Rick PD, Silver RP (1996) Enterobacterial common antigen and capsular polysaccharides. In: Neidhardt FC, Curtiss R III, Ingraham JL, Lin ECC, Low BK, Magasanik B, Reznikoff WS, Riley M, Schaechter M, Umbarger HE (eds) Escherichia coli and Salmonella: cellular and molecular biology, 2nd edn. ASM Press, Washington, DC, pp 104–122
Karakawa WW, Fournier JM, Vann WF, Arbeit R, Schneerson R, Robbins JB (1985) Method for the serological typing of the capsular polysaccharides of Staphylococcus aureus. J Clin Microbiol 22:445–447
Morona JK, Morona R, Paton JC (1997) Characterization of the locus encoding the Streptococcus pneumoniae type 19 F capsular polysaccharide biosynthetic pathway. Mol Microbiol 23:751–763
Lew HC, Nikaido H, Makela PH (1978) Biosynthesis of uridine diphosphate N-acetylmannosaminuronic acid in rff mutants of Salmonella tryphimurium. J Bacteriol 136:227–233
Kawamura T, Ichihara N, Ishimoto N, Ito E (1975) Biosynthesis of uridine diphosphate N-acetyl-d-mannosaminuronic acid from uridine diphosphate N-acetyl-d-glucosamine in Escherichia coli: separation of enzymes responsible for epimerization and dehydrogenation. Biochem Biophys Res Commun 66:1506–1512
Kawamura T, Ishimoto N, Ito E (1979) Enzymatic synthesis of uridine diphosphate N-acetyl-d-mannosaminuronic acid. J Biol Chem 254:8457–8465
Kawamura T, Ishimoto N, Ito E (1982) UDP-N-acetyl-d-glucosamine 2′-epimerase from Escherichia coli. Meth Enzymol 83:515–519
Kawamura T, Kimura M, Yamamori S, Ito E (1978) Enzymatic formation of uridine diphosphate N-acetyl-d-mannosamine. J Biol Chem 253:3595–3601
Kiser KB, Lee JC (1998) Staphylococcus aureus cap5O and cap5P genes functionally complement mutations affecting enterobacterial common-antigen biosynthesis in Escherichia coli. J Bacteriol 180:403–406
Portoles M, Kiser KB, Bhasin N, Chan KH, Lee JC (2001) Staphylococcus aureus Cap5O has UDP-ManNAc dehydrogenase activity and is essential for capsule expression. Infect Immun 69:917–923
Meier-Dieter U, Starman R, Barr K, Mayer H, Rick PD (1990) Biosynthesis of enterobacterial common antigen in Escherichia coli. Biochemical characterization of Tn10 insertion mutants defective in enterobacterial common antigen synthesis. J Biol Chem 265:13490–13497
Kiser KB, Bhasin N, Deng L, Lee JC (1999) Staphylococcus aureus cap5P encodes a UDP-N-acetylglucosamine 2-epimerase with functional redundancy. J Bacteriol 181:4818–4824
Andersson M, Carlin N, Leontein K, Lindquist U, Slettengren K (1989) Structural studies of the O-antigenic polysaccharide of Escherichia coli O86, which possesses blood-group B activity. Carbohydr Res 185:211–223
Linnerborg M, Weintraub A, Widmalm G (1997) Structural studies of the O-antigen polysaccharide from Escherichia coli O138. Eur J Biochem 247:567–571
Haseley SR, Holst O, Brade H (1997) Structural and serological characterisation of the O-antigenic polysaccharide of the lipopolysaccharide from Acinetobacter haemolyticus strain ATCC 17906. Eur J Biochem 244:761–766
Kondakova AN, Kolodziejska K, Zych K, Senchenkova SN, Shashkov AS, Knirel YA, Sidorczyk Z (2003) Structure of the N-acetyl-l-rhamnosamine-containing O-polysaccharide of Proteus vulgaris TG 155 from a new Proteus serogroup, O55. Carbohydr Res 338:1999–2004
Wang Z, Larocque S, Vinogradov E, Brisson JR, Dacanay A, Greenwell M, Brown LL, Li J, Altman E (2004) Structural studies of the capsular polysaccharide and lipopolysaccharide O-antigen of Aeromonas salmonicida strain 80204-1 produced under in vitro and in vivo growth conditions. Eur J Biochem 271:4507–4516
Veremeichenko SN, Zdorovenko GM (2000) The distinctive features of the structure of the Pseudomonas fluorescens IMV 247 (biovar II) lipopolysaccharide. Mikrobiologiia 69:362–369
Knirel YA (1990) Polysaccharide antigens of Pseudomonas aeruginosa. Crit Rev Microbiol 17:273–304
Creuzenet C, Belanger M, Wakarchuk WW, Lam JS (2000) Expression, purification, and biochemical characterization of WbpP, a new UDP-GlcNAc C4 epimerase from Pseudomonas aeruginosa serotype O6. J Biol Chem 275:19060–19067
Zhao X, Creuzenet C, Belanger M, Egbosimba E, Li J, Lam JS (2000) WbpO, a UDP-N-acetyl-d-galactosamine dehydrogenase from Pseudomonas aeruginosa serotype O6. J Biol Chem 275:33252–33259
Miller WL, Matewish MJ, McNally DJ, Ishiyama N, Anderson EM, Brewer D, Brisson JR, Berghuis AM, Lam JS (2008) Flagellin glycosylation in Pseudomonas aeruginosa PAK requires the O-antigen biosynthesis enzyme WbpO. J Biol Chem 283:3507–3518
Kowal P, Wang PG (2002) New UDP-GlcNAc C4 epimerase involved in the biosynthesis of 2-acetamino-2-deoxy-l-altruronic acid in the O-antigen repeating units of Plesiomonas shigelloides O17. Biochemistry 41:15410–15414
Wang L, Huskic S, Cisterne A, Rothemund D, Reeves PR (2002) The O-antigen gene cluster of Escherichia coli O55:H7 and identification of a new UDP-GlcNAc C4 epimerase gene. J Bacteriol 184:2620–2625
Guo H, Li L, Wang PG (2006) Biochemical characterization of UDP-GlcNAc/Glc 4-epimerase from Escherichia coli O86:B7. Biochemistry 45:13760–13768
Rush JS, Alaimo C, Robbiani R, Wacker M, Waechter CJ (2010) A novel epimerase that converts GlcNAc-P-P-undecaprenol to GalNAc-P-P-undecaprenol in Escherichia coli O157. J Biol Chem 285:1671–1680
Caroff M, Brisson JR, Martin A, Karibian D (2000) Structure of the Bordetella pertussis 1414 endotoxin. FEBS Lett 477:8–14
Wenzel CQ, Daniels C, Keates RA, Brewer D, Lam JS (2005) Evidence that WbpD is an N-acetyltransferase belonging to the hexapeptide acyltransferase superfamily and an important protein for O-antigen biosynthesis in Pseudomonas aeruginosa PAO1. Mol Microbiol 57:1288–1303
Preston A, Thomas R, Maskell DJ (2002) Mutational analysis of the Bordetella pertussis wlb LPS biosynthesis locus. Microb Pathog 33:91–95
Allen A, Maskell D (1996) The identification, cloning and mutagenesis of a genetic locus required for lipopolysaccharide biosynthesis in Bordetella pertussis. Mol Microbiol 19:37–52
Miller WL, Wenzel CQ, Daniels C, Larocque S, Brisson JR, Lam JS (2004) Biochemical characterization of WbpA, a UDP-N-acetyl-d-glucosamine 6-dehydrogenase involved in O-antigen biosynthesis in Pseudomonas aeruginosa PAO1. J Biol Chem 279:37551–37558
Westman EL, McNally DJ, Charchoglyan A, Brewer D, Field RA, Lam JS (2009) Characterization of WbpB, WbpE, and WbpD and reconstitution of a pathway for the biosynthesis of UDP-2,3-diacetamido-2,3-dideoxy-d-mannuronic acid in Pseudomonas aeruginosa. J Biol Chem 284:11854–11862
Larkin A, Imperiali B (2009) Biosynthesis of UDP-GlcNAc(3NAc)A by WbpB, WbpE, and WbpD: enzymes in the Wbp pathway responsible for O-antigen assembly in Pseudomonas aeruginosa PAO1. Biochemistry 48:5446–5455
Larkin A, Olivier NB, Imperiali B (2010) Structural analysis of WbpE from Pseudomonas aeruginosa PAO1: a nucleotide sugar aminotransferase involved in O-antigen assembly. Biochemistry 49:7227–7237
Rejzek M, Sri Kannathasan V, Wing C, Preston A, Westman EL, Lam JS, Naismith JH, Maskell DJ, Field RA (2009) Chemical synthesis of UDP-Glc-2,3-diNAcA, a key intermediate in cell surface polysaccharide biosynthesis in the human respiratory pathogens B. pertussis and P. aeruginosa. Org Biomol Chem 7:1203–1210
Westman EL, McNally DJ, Rejzek M, Miller WL, Kannathasan VS, Preston A, Maskell DJ, Field RA, Brisson JR, Lam JS (2007) Identification and biochemical characterization of two novel UDP-2,3-diacetamido-2,3-dideoxy-α-d-glucuronic acid 2-epimerases from respiratory pathogens. Biochem J 405:123–130
Westman EL, Preston A, Field RA, Lam JS (2008) Biosynthesis of a rare di-N-acetylated sugar in the lipopolysaccharides of both Pseudomonas aeruginosa and Bordetella pertussis occurs via an identical scheme despite different gene clusters. J Bacteriol 190:6060–6069
Bystrova OV, Lindner B, Moll H, Kocharova NA, Knirel YA, Zähringer U, Pier GB (2003) Structure of the biological repeating unit of the O-antigen of Pseudomonas aeruginosa immunotype 4 containing both 2-acetamido-2,6-dideoxy-d-glucose and 2-acetamido-2,6-dideoxy-d-galactose. Carbohydr Res 338:1801–1806
Rocchetta HL, Burrows LL, Lam JS (1999) Genetics of O-antigen biosynthesis in Pseudomonas aeruginosa. Microbiol Mol Biol Rev 63:523–553
Holst O (2002) Chemical structure of the core region of lipopolysaccharides – an update. Trends Glycosci Glyc 14:87–103
Raetz CR, Whitfield C (2002) Lipopolysaccharide endotoxins. Annu Rev Biochem 71:635–700
Gronow S, Brade H (2001) Lipopolysaccharide biosynthesis: which steps do bacteria need to survive? J Endotoxin Res 7:3–23
Cosgrove DJ (1997) Assembly and enlargement of the primary cell wall in plants. Annu Rev Cell Dev Biol 13:171–201
Cipolla L, Polissi A, Airoldi C, Galliani P, Sperandeo P, Nicotra F (2009) The Kdo biosynthetic pathway toward OM biogenesis as target in antibacterial drug design and development. Curr Drug Discov Technol 6:19–33
Ghalambor MA, Heath EC (1966) The biosynthesis of cell wall lipopolysaccharide in Escherichia coli. IV. Purification and properties of cytidine monophosphate 3-deoxy-d-manno-octulosonate synthetase. J Biol Chem 241:3216–3221
Raetz CR (1990) Biochemistry of endotoxins. Annu Rev Biochem 59:129–170
Sperandeo P, Pozzi C, Deho G, Polissi A (2006) Non-essential KDO biosynthesis and new essential cell envelope biogenesis genes in the Escherichia coli yrbG-yhbG locus. Res Microbiol 157:547–558
Meredith TC, Woodard RW (2005) Identification of GutQ from Escherichia coli as a d-arabinose 5-phosphate isomerase. J Bacteriol 187:6936–6942
Hedstrom L, Abeles R (1988) 3-Deoxy-d- manno-octulosonate-8-phosphate synthase catalyzes the C-O bond cleavage of phosphoenolpyruvate. Biochem Biophys Res Commun 157:816–820
Ray PH, Benedict CD (1980) Purification and characterization of specific 3-deoxy-d- manno-octulosonate 8-phosphate phosphatase from Escherichia coli B. J Bacteriol 142:60–68
Radaev S, Dastidar P, Patel M, Woodard RW, Gatti DL (2000) Preliminary X-ray analysis of a new crystal form of the Escherichia coli KDO8P synthase. Acta Crystallogr D Biol Crystallogr 56:516–519
Duewel HS, Radaev S, Wang J, Woodard RW, Gatti DL (2001) Substrate and metal complexes of 3-deoxy-d- manno-octulosonate-8-phosphate synthase from Aquifex aeolicus at 1.9-Å resolution. Implications for the condensation mechanism. J Biol Chem 276:8393–8402
Wu J, Woodard RW (2003) Escherichia coli YrbI is 3-deoxy-d- manno-octulosonate 8-phosphate phosphatase. J Biol Chem 278:18117–18123
Goldman RC, Kohlbrenner WE (1985) Molecular cloning of the structural gene coding for CTP:CMP-3-deoxy-manno-octulosonate cytidylyltransferase from Escherichia coli K-12. J Bacteriol 163:256–261
Eidels L, Osborn MJ (1971) Lipopolysaccharide and aldoheptose biosynthesis in transketolase mutants of Salmonella typhimurium. Proc Natl Acad Sci USA 68:1673–1677
Eidels L, Osborn MJ (1974) Phosphoheptose isomerase, first enzyme in the biosynthesis of aldoheptose in Salmonella typhimurium. J Biol Chem 249:5642–5648
Kocsis B, Kontrohr T (1984) Isolation of adenosine 5′-diphosphate-l- glycero-d- manno-heptose, the assumed substrate of heptose transferase(s), from Salmonella minnesota R595 and Shigella sonnei Re mutants. J Biol Chem 259:11858–11860
Coleman WG Jr (1983) The rfaD gene codes for ADP-l- glycero-d- manno-heptose-6-epimerase. An enzyme required for lipopolysaccharide core biosynthesis. J Biol Chem 258:1985–1990
Brooke JS, Valvano MA (1996) Biosynthesis of inner core lipopolysaccharide in enteric bacteria identification and characterization of a conserved phosphoheptose isomerase. J Biol Chem 271:3608–3614
Valvano MA, Marolda CL, Bittner M, Glaskin-Clay M, Simon TL, Klena JD (2000) The rfaE gene from Escherichia coli encodes a bifunctional protein involved in biosynthesis of the lipopolysaccharide core precursor ADP-l- glycero-d- manno-heptose. J Bacteriol 182:488–497
Kneidinger B, Marolda C, Graninger M, Zamyatina A, McArthur F, Kosma P, Valvano MA, Messner P (2002) Biosynthesis pathway of ADP-l- glycero-β-d- manno-heptose in Escherichia coli. J Bacteriol 184:363–369
Valvano MA, Messner P, Kosma P (2002) Novel pathways for biosynthesis of nucleotide-activated glycero-manno-heptose precursors of bacterial glycoproteins and cell surface polysaccharides. Microbiology 148:1979–1989
Mendez C, Luzhetskyy A, Bechthold A, Salas JA (2008) Deoxysugars in bioactive natural products: development of novel derivatives by altering the sugar pattern. Curr Top Med Chem 8:710–724
Salas JA, Mendez C (2007) Engineering the glycosylation of natural products in actinomycetes. Trends Microbiol 15:219–232
Thibodeaux CJ, Melancon CE, Liu HW (2007) Unusual sugar biosynthesis and natural product glycodiversification. Nature 446:1008–1016
Acknowledgements
Research in the Lam laboratory is supported by operating grants from the Canadian Institute of Health Research (#MOP-14687), and the Canadian Cystic Fibrosis Foundation. J.S.L. holds a Canada Research Chair in Cystic Fibrosis and Microbial Glycobiology jointly funded by the Canadian Foundation of Innovation and the Ontario Research Fund.
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Hao, Y., Lam, J.S. (2011). Pathways for the Biosynthesis of NDP Sugars. In: Knirel, Y., Valvano, M. (eds) Bacterial Lipopolysaccharides. Springer, Vienna. https://doi.org/10.1007/978-3-7091-0733-1_7
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