Core Region and Lipid A Components of Lipopolysaccharides

Microbial Glycobiology

Volumn , Issue , 2010, Pages 29-55

  Holst, Otto ^a   Molinaro, Antonio ^b  

^a RESEARCH CENTER BORSTEL   (Germany)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882885067     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-374546-0.00003-1     Document Type: Chapter

References (124)

1. Akira S., Uematsu S., Osamu T. Pathogen recognition and innate immunity. Cell 2006, 124:783-801.
2. Alexander C., Zähringer U. Chemical structure of lipid A - the primary immunomodulatory center of bacterial lipopolysaccharides. Trends Glycosci. Glycotech. 2002, 14:69-86.
3. Basu S.S., Karbarz M.J., Raetz C.H.R. Expression cloning and characterization of the c28 acyltransferase of lipid A biosynthesis in Rhizobium leguminosarum. J. Biol. Chem. 2002, 277:28959-28971.
4. Beutler B., Rietschel E.Th. Innate immune sensing and its roots: the story of endotoxin. Nat. Rev. Immunol. 2003, 3:169-176.
5. Bhat U.R., Forsberg L.S., Carlson R.W. Structure of lipid A component of Rhizobium leguminosarum bv. phaseoli lipopolysaccharide. Unique nonphosphorylated lipid A containing 2-amino-2-deoxygluconate, galacturonate, and glucosamine. J. Biol. Chem. 1994, 269:14402-14410.
6. Bouchet V., Hood D.W., Li J., et al. Host-derived sialic acid is incorporated into Haemophilus influenzae lipopolysaccharide and is a major virulence factor in experimental otitis media. Proc. Natl. Acad. Sci. USA 2003, 100:8898-8903.
7. Brade H., Brunner H. Serological cross-reactions between Acinetobacter calcoaceticus and chlamydiae. J. Clin. Microbiol. 1979, 10:819-822.
8. Brandenburg K., Seydel U., Schromm A.B., Loppnow H., Koch M.H.J., Rietschel E.Th. Conformation of lipid A, the endotoxic center of bacterial lipopolysaccharides. J. Endotoxin Res. 1996, 3:173-178.
9. Braun S.G., Meyer A., Holst O., Pühler A., Niehaus K. Characterization of the Xanthomonas campestris pv. campestris lipopolysaccharide substructures essential for elicitation of an oxidative burst in tobacco cells. Mol. Plant Microbe Interact. 2005, 18:674-681.
10. Brecker L. Nuclear magnetic resonance of lipid A: the influence of solvents on spin relaxation and spectral quality. Chem. Phys. Lipids 2003, 125:27-39.
11. Bystrova O.V., Lindner B., Moll H., et al. Structure of the lipopolysaccharide of Pseudomonas aeruginosa O-12 with a randomly O-acetylated core region. Carbohydr. Res. 2003, 338:1895-1905.
12. Bystrova O.V., Lindner B., Moll H., et al. Full structure of the lipopolysaccahride of Pseudomonas aeruginosa immunotype 5. Biochemistry (Moscow) 2004, 69:170-175.
13. Bystrova O.V., Knirel Y.A., Lindner B., et al. Structures of the core oligosaccharides and O-units in the R- and SR-type lipopolysaccharides of reference strains of Pseudomonas aeruginosa O-serogroups. FEMS Immunol. Med. Microbiol. 2006, 46:85-99.
14. Choma A., Komaniecka I. Characterization of a novel lipid A structure isolated from Azospirillum lipoferum lipopolysaccharide. Carbohydr. Res. 2008, 343:799-804.
15. Choudhury B., Carlson R.W., Goldberg J.B. The structure of the lipopolysaccharide from a galU mutant of Pseudomonas aeruginosa serogroup-O11. Carbohydr. Res. 2005, 343:2761-2772.
16. Choudhury B., Carlson R.W., Goldberg J.B. Characterization of the lipopolysaccharide from a wbjE mutant of the serogroup O11 Pseudomonas aeruginosa strain, PA103. Carbohydr. Res. 2008, 343:238-248.
17. Cox A.D., Li J., Brisson J.-R., Moxon E.R., Richards J.C. Structural analysis of the lipopolysaccharide from Neisseria meningitides strain BZ157 galE: localization of two phosphoethanolamine residues in the inner core oligosaccharide. Carbohydr. Res. 2002, 337:1435-1444.
18. Cox A.D., Hodd D.W., Martin A., et al. Identification and structural characterization of a sialylated lacto-N-neotetraose structure in the lipopolysaccharide of Haemophilus influenzae. Eur. J. Biochem. 2002, 269:4009-4019.
19. Cox A.D., Li J., Richards J.C. Identification and localization of glycine in the inner core lipopolysaccharide of Neisseria meningitidis. Eur. J. Biochem. 2002, 269:4169-4175.
20. Cox A.D., Howard M.D., Inzana T.J. Structural analysis of the lipooligosaccharide from the commensal Haemophilus somnus strain 1P. Carbohydr. Res. 2003, 338:1223-1228.
21. Cox A.D., Wright J.C., Gidney M.A.J., et al. Identification of a novel inner-core oligosaccharide structure in Neisseria meningitidis lipopolysaccharide. Eur. J. Biochem. 2003, 270:1759-1766.
22. Deadman M.E., Lundström S.L., Schweda E.K.H., Moxon E.R., Hood D.W. Specific amino acids of the glycosyltransferase LpsA direct the addition of glucose or galactose to the terminal inner core heptose of Haemophilus influenzae lipopolysaccharide via alternative linkages. J. Biol. Chem. 2006, 281:29455-29467.
23. De Castro C., Molinaro A., Nunziata R., Lanzetta R., Parrilli M., Holst O. A novel core region, lacking heptose and phosphate, of the lipopolysaccharide from the Gram-negative bacterium Pseudomonas cichorii (Pseudomonadaceae RNA group I). Eur. J. Org. Chem. 2004, 2427-2435.
24. De Castro C., Molinaro A., Lanzetta R., Holst O., Parrilli M. The linkage between O-specific caryan and core region in the lipopolysaccharide of Burkholderia caryophylli is furnished by a primer monosaccharide. Carbohydr. Res. 2005, 340:1802-1807.
25. De Castro C., Carannante A., Lanzetta R., Liparoti V., Molinaro A., Parrilli M. Core oligosaccharide structure from the highly pathogenic Agrobacterium tumefaciens TT111 and conformational analysis of the putative rhamnan epitope. Glycobiology 2006, 16:1272-1280.
26. De Castro C., Carannante A., Lanzetta R., et al. Structural characterisation of the core oligosaccharides isolated from the lipooligosaccharide fraction of Agrobacterium tumefaciens A1. Chem. Eur. J. 2006, 12:4668-4674.
27. De Castro C., Molinaro A., Lanzetta R., Silipo A., Parrilli M. Lipopolysaccharide structures from Agrobacterium and other Rhizobiaceae species. Carbohydr. Res. 2008, 343:1924-1933.
28. De Soyza A., Silipo A., Lanzetta R., Govan J.R., Molinaro A. The chemical and biological features of Burkholderia cepacia complex lipopolysaccharides. Innate Immun. 2008, 14:127-144.
29. Dow J.M., Newman M.-A., von Roepenack E. The induction and modulation of plant defence responses by bacterial lipopolysaccharides. Annu. Rev. Phytopathol. 2000, 38:241-261.
30. Fox K.L., Yildrim H.H., Deadman M.E., Schweda E.K.H., Moxon E.R., Hood D.W. Novel lipopolysaccharide biosynthetic genes containing tetranucleotide repeats in Haemophilus influenzae, identification of a gene for adding O-acetyl groups. Mol. Microbiol. 2005, 58:207-216.
31. Gass J., Strobl M., Loibner A., Zähringer U. Synthesis of allyl O-[sodium (α-d-glycero-d-talo-2-octulopyranosyl)onate]-(2→6)-2-acetamid o-2-deoxy-β-d-glucopyranoside, a core constituent of the lipopolysaccharide from Acinetobacter calcoaceticus NCTC 10305. Carbohydr. Res. 1993, 244:69-84.
32. Griffin R., Cox A.D., Makepeace K., Richards J.C., Moxon E.R., Hood D.W. The role of lex2 in lipopolysaccharide biosynthesis in Haemophilus influenzae strains RM7004 and RM153. Microbiology 2003, 149:3165-3175.
33. Hanuszkiewicz A., Hübner G., Vinogradov E., et al. Structural and immunochemical analysis of the lipopolysaccharide from Acinetobacter lwoffii F78 located outside Chlamydiaceae with a Chlamydia-specific lipopolysaccharide epitope. Chem. Eur. J. 2008, 14:10251-10258.
34. Harper M., Cox A.D., St Michael F., Wilkie I.W., Boyce J.D., Adler B. A heptosayltransferase mutant of Pasteurella multocida produces a truncated lipopolysaccharide structure and is attenuated in virulence. Infect. Immun. 2004, 72:3436-3443.
35. Harper M., Boyce J.D., Cox A.D., et al. Pasteurella multocida espresses two lipopolysaccharide glycoforms simultaneously, but only a single form is required for virulence: identification of two acceptor-specific heptosyl I transferases. Infect. Immun. 2007, 75:3885-3893.
36. Hashii N., Isshiki Y., Iguchi T., Kondo S. Structural characterization of the carbohydrate backbone of the lipopolysaccharide of Vibrio parahaemolyticus O-untypeable strain KX-V212 isolated from a patient. Carbohydr. Res. 2003, 338:2711-2719.
37. Holst O. Chemical structure of the core region of lipopolysaccharides. Endotoxin in Health and Disease 1999, 115-154. Marcel Dekker, New York. H. Brade, S.M. Opal, S.N. Vogel, D.C. Morrison (Eds.).
38. Holst O. Deacylation of lipopolysaccharides and isolation of oligosaccharide phosphates. Methods in Molecular Biology: Bacterial Toxins 2000, 345-353. Humana Press, Totowa. O. Holst (Ed.).
39. Holst O. Chemical structure of the core region of lipopolysaccharides - an update. Trends. Glycosci. Glycotech. 2002, 14:87-103.
40. Holst O. The structures of core regions from enterobacterial lipopolysaccharides - an update. FEMS Microbiol. Lett. 2007, 271:3-11.
41. Holst O., Brade H. Chemical structure of the core region of lipopolysaccharides. Bacterial Endotoxic Lipopolysaccharides 1992, Vol. I:135-170. Boca Raton, CRC Press. D.C. Morrison, J.L. Ryan (Eds.).
42. Holst O., Müller-Loennies S. Microbial polysaccharide structures. Comprehensive Glycoscience. From Chemistry to Systems Biology 2007, Vol. 1:123-179. Elsevier Ltd, Oxford. J.P. Kamerling, G.-J. Boons, Y.C. Lee, A. Suzuki, N. Taniguchi, A.G.J. Voragen (Eds.).
43. Imoto M., Shiba T., Naoki H., et al. Chemical structure of E. coli lipid A: linkage site of acyl groups in the disaccharide backbone. Tetrahedron Lett. 1983, 24:4017-4020.
44. Inzana T.J., Glindemann G., Cox A.D., Wakarchuk W., Howard M.D. Incorporation of N-acetylneuraminic acid into Haemophilus somnus lipooligosaccharide (LOS): enhancement of resistance to serum and reduction of LOS antibody binding. Infect. Immun. 2002, 70:4870-4879.
45. Isshiki Y., Zähringer U., Kawahara K. Structure of the core oligosaccharide with a characteristic d-glycero-α-d-talo-oct-2-ulosonate-(2→4)-3-deoxy-d-manno-oct- 2-ulosonate [α-Ko-(2→4)-Kdo] disaccharide in the lipopolysaccharide of Burkholderia cepacia. Carbohydr. Res. 2003, 338:2659-2666.
46. Jones J.D.G., Dangl J.L. The plant immune system. Nature 2006, 444:323-329.
47. Kaczyski Z., Braun S., Lindner B., Niehaus K., Holst O. Investigation of the chemical structure and biological activity of oligosaccharides isolated from rough-type Xanthomonas campestris pv. campestris B100 lipopolysaccharides. J. Endotoxin Res. 2007, 13:101-108.
48. Kay W., Petersen B.O., Duus J.Ø., Perry M.B., Vinogradov E. Characterization of the lipopolysaccharide and β-glucan of the fish pathogen Francisella victoria. FEBS J. 2006, 273:3002-3013.
49. Knirel Y.A., Kochetkov N.K. The structure of lipopolysaccharides of gram-negative bacteria. II. The structure of the core region: a review. Biokhimya 1993, 58:182-201.
50. Knirel Y.A., Lindner B., Vinogradov E., et al. Temperature-dependent variations and intraspecies diversity of the structure of the lipopolysaccharide of Yersinia pestis. Biochemistry 2005, 44:1731-1743.
51. Knirel Y.A., Bystrova O.V., Kocharova N.A., Zähringer U., Pier G.B. Conserved and variable structural features in the lipopolysaccharide of Pseudomonas aeruginosa. J. Endotoxin Res. 2006, 12:324-336.
52. Kooistra O., Bedoux G., Brecker L., et al. Structure of a highly phosphorylated core in the ΔalgC mutant derived from Pseudomonas aeruginosa wild-type strains PAO1 (serogroup O5) and PAC1R (serogroup O3). Carbohydr. Res. 2003, 338:2667-2677.
53. Krasikova I.N., Kapustina N.V., Svetashev V.I., et al. Chemical characterization of lipid A from some marine proteobacteria. Biochemistry (Moscow) 2001, 66:1047-1054.
54. Krasikova I.N., Kapustina N.V., Isakov V.V., et al. Detailed structure of lipid A isolated from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119. Eur. J. Biochem. 2004, 271:2895-2904.
55. Leone S., Izzo V., Silipo A., et al. A novel type of highly negatively charged lipooligosaccharide from Pseudomonas stutzeri OX1 possessing two 4,6-O-(1-carboxy)-ethylidene residues in the outer core region. Eur. J. Biochem. 2004, 271:2691-2704.
56. Leone S., Izzo V., Sturiale L., et al. Structure of minor oligosaccharides from the lipopolysaccharide fraction of Pseudomonas stutzeri OX1. Carbohydr. Res. 2004, 339:2657-2665.
57. Leone S., Molinaro A., Pessione E., et al. Structural elucidation of the core-lipid A backbone from the lipopolysaccharide of Acinetobacter radioresistens S13, an organic solvent tolerating Gram-negative bacterium. Carbohydr. Res. 2006, 341:582-590.
58. Leone S., Molinaro A., De Castro C., et al. Absolute configuration of 8-amino-3,8-dideoxyoct-2-ulosonic acid, the chemical hallmark of lipopolysaccharides of the genus Shewanella. J. Nat. Prod. 2007, 70:1624-1627.
59. Liparoti V., Molinaro A., Sturiale L., et al. Structural analysis of the deep rough lipopolysaccharide from Gram negative bacterium Alteromonas macleodii ATCC 27126: the first finding of β-Kdo in the inner core of lipopolysaccharides. Eur. J. Org. Chem. 2006, 2006:4710-4716.
60. Lundström S.L., Twelkmeyer B., Sagemark M.K., et al. Novel globoside-like oligosaccharide expression patterns in non-typeable Haemophilus influenzae lipopolysaccharide. FEBS J. 2007, 274:4886-4903.
61. Månsson M., Hood D.W., Li J., Richards J.C., Moxon E.R., Schweda E.K.H. Structural analysis of the lipopolysaccharide from nontypeable Haemophilus influenzae strain 1003. Eur. J. Biochem. 2002, 269:808-818.
62. Månsson M., Hood D.W., Moxon E.R., Schweda E.K.H. Structural characterization of a novel branching pattern in the lipopolysaccharide from nontypeable Haemophilus influenzae. Eur. J. Biochem. 2003, 270:2979-2991.
63. Marr N., Tirsoaga A., Blanot D., Fernandez R., Caroff M. Glucosamine found as a substituent of both phosphate groups in Bordetellae lipid A backbones: role of a BvgAS-activated ArnT ortholog. J. Bacteriol. 2008, 190:4281-4290.
64. Medzhitov R. Toll-like receptors and innate immunity. Nat. Rev. Immunol. 2001, 1:135-145.
65. Molinaro A., Lindner B., De Castro C., et al. The structure of the lipid A of the lipopolysaccharide from Burkholderia caryophylli possessing a 4-amino-4-deoxy-l-arabinopyranose-1-phosphate residue exclusively in glycosidic linkage. Chem. Eur. J. 2003, 9:1542-1548.
66. Molinaro A., De Castro C., Lanzetta R., Parrilli M., Raio A., Zoina A. Structural elucidation of a novel core oligosaccharide backbone of the lipopolysaccharide from the new bacterial species Agrobacterium larrymoorei. Carbohydr. Res. 2003, 338:2721-2730.
67. + of Haemophilus influenzae. Eur. J. Biochem. 2002, 269:1237-1242.
68. Müller-Loennies S., Lindner B., Brade H. Structural analysis of deacylated lipopolysaccharide of Escherichia coli strains 2513 (R4 core-type) and F653 (R3 core-type). Eur. J. Biochem. 2002, 269:5982-5991.
69. Munford S.R. Sensing Gram-negative bacterial lipopolysaccharides: a human disease determinant?. Infect. Immun. 2008, 76:454-465.
70. Munford S.R., Varley A.W. Shield as signal: lipopolysaccharides and the evolution of immunity to Gram-negative bacteria. PLoS Pathog. 2006, 2:467-471.
71. Newman M.-A., von Roepenack-Lahaye E., Parr A., Daniels M.J., Dow J.M. Prior exposure to lipopolysaccharide potentiates expression of plant defences in response to bacteria. Plant J. 2002, 29:485-497.
72. Newman M.-A., Dow J.M., Molinaro A., Parrilli M. Priming, induction and modulation of plant defence responses by bacterial lipopolysaccharides. J. Endotox. Res. 2007, 13:69-84.
73. Ortega X.P., Cardona S.T., Brown A.R., et al. A putative gene cluster for aminoarabinose biosynthesis is essential for Burkholderia cenocepacia viability. J. Bacteriol. 2007, 189:3639-3644.
74. Pieretti G., Corsaro M.M., Lanzetta R., et al. Structural characterization of the core region of the lipopolysaccharide from the haloalkaliphilic Halomonas pantellerensis: identification of the biological O-antigen repeating unit. Eur. J. Org. Chem. 2008, 2008:721-728.
75. Plötz B.M., Lindner B., Stetter K.O., Holst O. Characterization of a novel lipid A containing d-galacturonic acid that replaces phosphate residues. The structure of the lipid A of the lipopolysaccharide from the hyperthermophilic bacterium Aquifex pyrophilus. J. Biol. Chem. 2000, 275:11222-11228.
76. Que N.L.S., Lin S.H., Cotter R.J., Raetz C.H.R. Purification and mass spectrometry of six lipid a species from the bacterial endosymbiont Rhizobium etli. J. Biol. Chem. 2000, 275:28006-28016.
77. Raetz C.R.H., Whitfield C. Lipopolysaccharide endotoxins. Annu. Rev. Biochem. 2002, 71:635-700.
78. Raetz C.R.H., Reynolds C.M., Trent M.S., Bishop R.E. Lipid A modification systems in gram-negative bacteria. Annu. Rev. Biochem. 2007, 76:295-329.
79. Ribeiro A.A., Zhou Z., Raetz C.R.H. Multi-dimensional NMR structural analyses of purified Lipid X and Lipid A (endotoxin). Magn. Reson. Chem. 1999, 37:620-630.
80. Rietschel E.Th. Absolute configuration of 3-hydroxy fatty acids present in lipopolysaccharides from various bacterial groups. Eur. J. Biochem. 1976, 64:423-428.
81. Rietschel E.Th., Westphal O. Endotoxins: historical perspectives. Endotoxin in Health and Disease 1999, 1-30. Marcel Dekker Inc, New York. H. Brade, D.C. Morrison, S. Opal, S. Vogel (Eds.).
82. Schweda E.K.H., Landerholm M.K., Li J., Moxon E.R., Richards J.C. Structural profiling of lipopolysaccharide glycoforms expressed by non-typeable Haemophilus influenzae: phenotypic similarities between NTHi strain 162 and the genome strain Rd. Carbohydr. Res. 2003, 338:2731-2744.
83. Schweda E.K.H., Twelkmeyer B., Li J. Profiling structural elements of short-chain lipopolysaccharide of non-typeable Haemophilus influenzae. Innate Immun. 2008, 14:199-211.
84. Schwudke D., Linscheid M., Strauch E., et al. The obligate predatory Bdellovibrio bacteriovorus possesses a neutral lipid A containing α-d-mannoses that replace phosphate residues: similarities and differences between the lipid As and the lipopolysaccharides of the wild type strain B. bacteriovorus HD100 and its host-independent derivative HI100. J. Biol. Chem. 2003, 278:27502-27512.
85. Seydel U., Labischinski H., Kastowsky M., Brandenburg K. Phase behaviour, supramolecular structure, and molecular conformation of lipopolysaccharide. Immunobiology 1993, 187:191-211.
86. Seydel U., Oikawa M., Fukase K., Kusumoto S., Brandenburg K. Intrinsic conformation of lipid A is responsible for agonistic and antagonistic activity. Eur. J. Biochem. 2000, 267:3032-3039.
87. Sforza S., Silipo A., Molinaro A., Marchelli R., Parrilli M., Lanzetta R. Determination of fatty acid positions in native lipid A by positive and negative electrospray ionization mass spectrometry. J. Mass Spectrom. 2004, 39:378-383.
88. Shear M.J., Turner F.C. Chemical treatment of tumors. VII. Nature of hemorrhage-producing fraction from Serrati marcescens (Bacillus prodigiosus) culture filtrates. J. Natl. Cancer Inst. 1943, 4:107-122.
89. Silipo A., Lanzetta R., Amoresano A., Parrilli M., Molinaro A. Ammonium hydroxide hydrolysis: a valuable support in the MALDI-TOF mass spectrometry analysis of lipid A fatty acid distribution. J. Lipid Res. 2002, 43:2188-2195.
90. Silipo A., De Castro C., Lanzetta R., Molinaro A., Parrilli M. Full structural characterization of the lipid A components from the Agrobacterium tumefaciens strain C58 lipopolysaccharide fraction. Glycobiology 2004, 14:805-815.
91. Silipo A., Sturiale L., Garozzo D., et al. Structure elucidation of the highly heterogeneous lipid A from the lipopolysaccharide of the Gram-negative extremophile bacterium Halomonas magadiensis strain 21 M1. Eur. J. Org. Chem 2004, 2004:2263-2271.
92. Silipo A., Molinaro A., Cescutti P., et al. Complete structural characterization of the lipid A fraction of a clinical strain of Burkholderia cepacia genomovar I lipopolysaccharide. Glycobiology 2005, 15:561-570.
93. Silipo A., Lanzetta R., Parrilli M., et al. The complete structure of the core carbohydrate backbone from the LPS of marine halophilic bacterium Pseudoalteromonas carrageenovora type strain IAM 12662. Carbohydr. Res. 2005, 340:1475-1482.
94. Silipo A., Molinaro A., Nazarenko E.L., et al. Structural characterization of the carbohydrate backbone of the lipooligosaccharide of the marine bacterium Arenibacter certesii strain KMM 3941. Carbohydr. Res. 2005, 340:2540-2549.
95. Silipo A., Molinaro A., Sturiale L., et al. The elicitation of plant innate immunity by lipooligosaccharide of Xanthomonas campestris. J. Biol. Chem. 2005, 280:33660-33668.
96. Silipo A., Molinaro A., Comegna D., et al. Full structural characterization of the lipooligosaccharide of a Burkholderia pyrrocina clinical isolate. Eur. J. Org. Chem. 2006, 2006:4874-4883.
97. Silipo A., Sturiale L., Garozzo D., et al. The acylation and phosphorylation pattern of lipid A strongly influence its ability to trigger the innate immune response in Arabidopsis: Xanthomonas campestris pv. campestris mutant strain 8530 synthesizes a chemically different LPS that it is not recognized by innate immunity in plants. Chembiochem 2008, 9:896-904.
98. St Michael F., Howard M.D., Li J., Duncan A.J., Inzana T.J., Cox A.D. Structural analysis of the lipooligosaccharide from the commensal Haemophilus somnus genome strain 129Pt. Carbohydr. Res. 2004, 339:529-535.
99. St Michael F., Brisson J.-R., Larocque S., et al. Structural analysis of the lipoopolysaccharide derived core oligosaccharides of Actinobacillus pleuropneumoniae serotypes 1, 2, 5a and the genome strain 5b. Carbohydr. Res. 2004, 339:1973-1984.
100. St Michael F., Li J., Vinogradov E., Larocque S., Harper M., Cox A.D. Structural analysis of the lipooligosaccharide of Pasteurella multocida strain VP161: identification of both Kdo-P and Kdo-Kdo species in the lipopolysaccharide. Carbohydr. Res. 2005, 340:59-68.
101. St Michael F., Li J., Howard M.D., Duncan A.J., Inzana T.J., Cox A.D. Structural analysis of the oligosaccharide of Histophilus somni (Haemophilus somnus) strain 2336 and identification of several lipooligosaccharide biosynthesis gene homologues. Carbohydr. Res. 2005, 340:665-672.
102. St Michael F., Li J., Cox A.D. Structural analysis of the core oligosaccharide of Pasteurella multocida strain X73. Carbohydr. Res. 2005, 340:1253-1257.
103. St Michael F., Vinogradov E., Li J., Cox A.D. Structural analysis of the lipopolysaccharide of Pasteurella multocida strain Pm70 and identification of the putative lipopolysaccharide glycosyltransferases. Glycobiology 2005, 15:323-333.
104. St Michael F., Inzana T.J., Cox A.D. Structural analysis of the lipooligosaccharide-derived oligosaccharide of Histophilus somni (Haemophilus somnus) strain 8025. Carbohydr. Res. 2006, 341:281-284.
105. Sturiale L., Garozzo D., Silipo A., Lanzetta R., Parrilli M., Molinaro A. MALDI mass spectrometry of native bacterial lipooligosaccharides. Rapid Commun. Mass Spectrom. 2005, 19:1829-1834.
106. Takayama K., Qureshi N., Mascagni P. Complete structures of lipid A obtained from the lipopolysaccharide of the heptoseless mutant of Salmonella typhimurium. J. Biol. Chem. 1983, 258:12801-12803.
107. Tinnert A.-S., Månsson M., Yildrim H.H., Hood D.W., Schweda E.K.H. Structural investigation of lipooligosaccharides from non-typeable Haemophilus influenzae: investigation of inner-core phosphoethanolamine addition in NTHi strain 981. Carbohydr. Res. 2005, 340:1900-1907.
108. Unger F.M. The chemistry and biological significance of 3-deoxy-d-manno-2-octulosonic acid (Kdo). Adv. Carbohydr. Chem. Biochem. 1983, 348:323-387.
109. Vedam V., Kannenberg E.L., Haynes J.G., Sherrier D., Datta, Carlson R.W. A Rhizobium leguminosarum AcpXL mutant produces lipopolysaccharide lacking 27-hydroxyoctacosanoic acid. J. Bacteriol. 2003, 185:1841-1850.
110. Vinogradov E., Duus J.Ø., Brade H., Holst O. The structure of the carbohydrate backbone of the lipopolysaccharide from Acinetobacter baumannii strain ATCC 19606. Eur. J. Biochem 2002, 269:422-430.
111. Vinogradov E., Korenevsky A., Beveridge T.J. The structure of the carbohydrate backbone of the LPS from Shewanella putrefaciens CN32. Carbohydr. Res. 2002, 337:1285-1289.
112. Vinogradov E., Korenevsky A., Beveridge T.J. The structure of the rough-type lipooligosaccharide from Shewanella oneidensis MR-1, containing 8-amino-8-deoxy-Kdo and an open-chain form of 2-acetamido-2-deoxy-d-galactose. Carbohydr. Res. 2003, 338:1991-1997.
113. Vinogradov E., Korenevsky A., Beveridge T.J. The structure of the core region of the lipopolyosaccharide from Shewanella algae BrY, containing 8-amino-3,8-dideoxy-d-manno-oct-2-ulosonic acid. Carbohydr. Res. 2004, 339:737-740.
114. Vinogradov E., Korenevsky A., Lovley D.R., Beveridge T.J. The structure of the core region of the lipopolyosaccharide from Geobacter sulfurreducens. Carbohydr. Res. 2004, 339:2901-2904.
115. Wang Z., Li J., Vinogradov E., Altman E. Structural studies of the core region of Aeromonas salmonicida subsp. salmonicida lipopolysaccharide. Carbohydr. Res. 2006, 341:109-117.
116. Wang Z., Li J., Altman E. Structural characterization of the lipid A region of Aeromonas salmonicida subsp. salmonicida lipopolysaccharide. Carbohydr. Res. 2006, 341:2816-2825.
117. Westphal O., Lüderitz O. Chemische Erforschung von Lipopolysacchariden gram-negativer Bakterien. Angew. Chem. 1954, 66:407-417.
118. Westphal O., Lüderitz O., Bister F. Uber die Extraktion von Bakterien mit Phenol/Wasser. Z. Naturforsch. 1952, 7:148-155.
119. Yildrim H.H., Li J., Richards J.C., Hood D.W., Moxon E.R., Schweda E.K.H. Complex O-acetylation in non-typeable Haemophilus influenzae lipopolysaccharide: evidence for a novel site of O-acetylation. Carbohydr. Res. 2005, 340:2598-2611.
120. Zähringer U., Lindner B., Rietschel E.Th. Molecular structure of lipid A, the endotoxic center of bacterial lipopolysaccharides. Adv. Carbohydr. Chem. Biochem. 1994, 50:211-276.
121. Zähringer U., Lindner B., Knirel Y.A., et al. Structure and biological activity of the short-chain lipopolysaccharide from Bartonella henselae ATCC 49882. J. Biol. Chem. 2004, 279:21046-21054.
122. Zdorovenko E.L., Vinogradov E., Zdorovenko G.M., et al. Structure of the core oligosaccharide of a rough-type lipopolysaccharide of Pseudomonas syringae pv. phaseolica. Eur. J. Biochem. 2004, 271:4968-4977.
123. Zeidler D., Zähringer U., Gerber I., et al. Innate immunity in Arabidopsis thaliana: lipopolysaccharides activate nitric oxide synthase (NOS) and induce defense genes. Proc. Natl. Acad. Sci. USA 2004, 101:15811-15816.
124. Zipfel C., Felix G. Plants and animals: a different taste for microbes?. Curr. Opin. Plant Pathol. 2005, 8:353-360.