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PubMed2001

Chemical structure of the core oligosaccharide of aerotolerant Campylobacter jejuni O:2 lipopolysaccharide.

The structure of the core oligosaccharide of aerotolerant Campylobacter jejuni 0:2 lipopolysaccharide was determined and found to contain 3-deoxy-D-manno-octulosonic acid (Kdo), L-glycero-D-manno-heptose (LD-Hep), D-galactose, D-glucose, and phosphorylethanolamine (PEtn). Based on 1H, 13C and 31P NMR spectroscopic studies including 2D COSY, TOCSY, ROESY and heteronuclear 1H-31P and HMQC experiments it was established that the oligosaccharide has the following structure: [structure: see text].

Campylobacter jejuni↗

PubMed1980

Studies on the partial structure of the O-antigen of Vibrio cholera, Inaba 569 B.

Five oligosaccharides were isolated in pure state from the lipopolysaccharide of Vibrio cholera, Inaba 569 B, the their structures were elucidated. More-detailed information regarding the partial structure of the lipopolysaccharide, containing glucose, mannose, glucuronic acid, 2-amino-2-deoxyglucose, D-glycero-L-mannoheptose, and D-glycero-L-gluco-heptose, was obtained through Smith degradation, chromium trioxide oxidation, and graded hydrolysis studies of the lipopolysaccharide and its derived products.

Antigens, Surface↗

PubMed1979

Lipopolysaccharides from Pseudomonas maltophilia: structural studies of the side-chain polysaccharide from strain N.C.T.C. 10257.

A lipopolysaccharide has been isolated from Pseudomonas maltophilia N.C.T.C. 10257. Monosaccharide components identified were L-rhamnose, 3-O-methyl-L-xylose, L-xylose, D-glucose, D-mannose, D-galacturonic acid, 2-amino-2-deoxy-galactose, 2-amino-2-deoxyglucose, and a 3-deoxy-2-octulosonic acid. Heptose was absent. In this and other respects, the lipopolysaccharide resembles the corresponding products from Xanthomonas species. Mild hydrolysis of the lipopolysaccharide with acid, followed by chromatography of the water-soluble products on Sephadex G-50, gave a polymeric, "side-chain" fraction containing rhamnose, 3-O-methylxylose, and xylose residues in the molar rations approximately 15:4:1. Methylation analysis, periodate oxidation, Smith degradation, and oxidation with chromium trioxide were the principal methods used in the study of this fraction. The following structure is proposed for the characteristic repeating-unit of the polymer.

Chemical Phenomena↗

PubMed1985

Structural studies of the antigenic polysaccharide of Eubacterium saburreum, strain T17.

The antigenic polysaccharide produced by Eubacterium saburreum, strain T17, is a homoglycan composed of D-glycero-D-galacto-heptose (Hep) residues having the pentasaccharide repeating-unit----6)-[alpha-Hepf-(1----4)] -beta-Hepp-(1----6)-[alpha-Hepf-(1----2), alpha-Hepf-(1----4)]-beta-Hepp-(1----. The polysaccharide does not contain O-acetyl group.

Carbohydrate Conformation↗

PubMed1992

Structure of the polysaccharide chains of Pseudomonas pseudomallei lipopolysaccharides.

The pathogenic bacterium Pseudomonas pseudomallei strain 57576 produces two partially O-acetylated O-antigenic polysaccharides (PS-I and PS-II). Methylation analysis and 1H and 13C NMR spectroscopy, including NOE experiments, showed PS-I to have the structure [formula: see text] and PS-II to have the structure [formula: see text] where 6dmanHep is the unusual higher sugar 6-deoxy-D-manno-heptose. PS-II is produced also by P. pseudomallei strains 100 and 110, and PS-I and O-deacetylated PS-II by strain 97.

Burkholderia pseudomallei↗

PubMed2002

Structural analysis of lipopolysaccharide oligosaccharide epitopes expressed by non-typeable Haemophilus influenzae strain 176.

The structure of the lipopolysaccharide (LPS) from non-typeable Haemophilus influenzae strain 176 has been investigated. Electrospray ionization-mass spectrometry (ESIMS) on O-deacylated LPS (LPS-OH) and core oligosaccharide (OS) samples obtained after mild-acid hydrolysis of LPS provided information on the composition and relative abundance of the glycoforms. ESIMS tandem-mass spectrometry on LPS-OH confirmed the presence of minor sialylated and disialylated glycoforms. Oligosaccharide samples were studied in detail using high-field NMR techniques. It was found that the LPS contains the common inner-core element of H. influenzae, L-alpha-D-Hepp-(1-->2)-[PEtn-->6]-L-alpha-D-Hepp-(1-->3)-[beta-D-Glcp-(1-->4)]-L-alpha-D-Hepp-(1-->5)-[PPEtn-->4]-alpha-Kdop-(2-->6)-Lipid A having glycosyl substitution at the O-3 position of the terminal heptose as recently observed for non-typeable H. influenzae strain 486 [Månsson, M.; Bauer, S. H. J.; Hood, D. W.; Richards, J. C.; Moxon, E. R.; Schweda, E. K. H., Eur. J. Biochem. 2001, 268, 2148--2159]. The following LPS structures were identified as the major glycoforms, the most significant being indicated with an asterisk (*) (glycoforms are partly substituted with Gly at the terminal Hep):

Carbohydrate Conformation↗

PubMed2002

Structure of the core part of the lipopolysaccharides from Proteus penneri strains 7, 8, 14, 15, and 21.

The core-lipid A region of the lipopolysaccharides from Proteus penneri strains 7, 8, 14, 15, and 21 was studied using NMR spectroscopy, ESI MS, and chemical analysis after alkaline deacylation, deamination, and mild-acid hydrolysis of the lipopolysaccharides. The following general structure of the major core oligosaccharides is proposed: [abstract: see text] where all sugars are in the pyranose form and have the D configuration unless otherwise stated, Hep and DDHep=L-glycero- and D-glycero-D-manno-heptose, respectively, K=H, and Q=H in strain 8 or alpha-Glc in strains 7, 14, 15, and 21. In addition, several minor structural variants are present, including those lacking Ara4N in strains 7 and 15 and having the alpha-GlcN residue N-acylated to a various degree with glycine in strains 7, 8, 14, and 21. In strain 14, there are also core oligosaccharides with K=amide of beta-D-GalpA with putrescine, spermidine, or 4-azaheptane-1,7-diamine; remarkably, these structural variants lack either the PEtN group or the alpha-Hep-(1-->2)-alpha-DDHep disaccharide fragment at alpha-D-GalpA. While structural features of the inner core part are shared by Proteus strains studied earlier, the outermost Q-(1-->4)-alpha-GalNAc-(1-->2)-alpha-DDHep-(1-->6)-alpha-GlcN oligosaccharide unit has not been hitherto reported.

Carbohydrate Conformation↗

PubMed2002

Structural analysis of the lipopolysaccharide from Neisseria meningitidis strain BZ157 galE: localisation of two phosphoethanolamine residues in the inner core oligosaccharide.

The structure of the phase-variable lipopolysaccharide (LPS) from the group B Neisseria meningitidis strain BZ157 galE was elucidated. The structural basis for the LPS's variation in reactivity with a monoclonal antibody (MAb) B5 that has specificity for the presence of phosphoethanolamine (PEtn) at the 3-position of the distal heptose residue (HepII) was established. The structure of the O-deacylated LPS was deduced by a combination of monosaccharide analyses, nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. These analyses revealed the presence of a novel inner core oligosaccharide (OS) structure in the MAb B5 reactive (B5+) LPS that contained two PEtn residues simultaneously substituting the 3- and 6-positions of the HepII residue. The determination of this structure has identified a further degree of variability within the inner core OS of meningococcal LPS that could contribute to the interaction of meningococcal strains with their host.

Acylation↗

PubMed2003

The structure of the antigenic polysaccharide produced by Eubactrium saburreum T15.

The antigenic polysaccharide was obtained from the cell wall of Eubacterium saburreum strain T15 by trypsin digestion followed by gel permeation and ion-exchange chromatography. Its structure was determined using acid hydrolysis, methylation analysis, and 1D and 2D NMR spectroscopy. It contained L-threo-pent-2-ulose (Xul), D-fucose (Fuc), and D-glycero-D-galacto-heptose (Hep) in 2:3:3 ratio. Methylation analysis indicated an octasaccharide repeating-unit containing five branches. The 1H and 13C signals in NMR spectra of the sugar residues were assigned by COSY, HOHAHA, and HMQC 2D experiments, and the sequence of sugar residues in the repeating unit was determined by NOESY and HMBC experiments. The polysaccharide also contains two O-acetyl groups in the repeating unit, located on the Hep residue. The repeating structure can be written as: [see text for equation]. This is a novel structure in bacterial cell-wall polysaccharides from Gram-positive bacteria.

Carbohydrate Conformation↗

PubMed2003

Structural analysis of the lipooligosaccharide from the commensal Haemophilus somnus strain 1P.

The structure of the lipooligosaccharide (LOS) from the commensal Haemophilus somnus strain 1P was elucidated. The structure of the O-deacylated LOS was established by monosaccharide analysis, NMR spectroscopy and mass spectrometry. The following structure for the O-deacylated LOS was determined on the basis of the combined data from these experiments. [chemical structure: see text] In the structure Kdo is 3-deoxy-D-manno-octulosonic acid, Hep is L-glycero-D-manno-heptose and lipid A-OH refers to O-deacylated Lipid A. The elucidation of this structure has increased our understanding of the relationship between the variability in LOS structure and the pathogenic potential of this organism. Specifically, the inability of this commensal strain to sialylate its LOS suggests that LOS sialylation could be a crucial virulence factor for H. somnus.

Haemophilus↗

PubMed2003

The structure of the rough-type lipopolysaccharide from Shewanella oneidensis MR-1, containing 8-amino-8-deoxy-Kdo and an open-chain form of 2-acetamido-2-deoxy-D-galactose.

The LPS from Shewanella oneidensis strain MR-1 was analysed by chemical methods and by NMR spectroscopy and mass spectrometry. The LPS contained no polysaccharide O-chain, and its carbohydrate backbone had the following structure: (1S)-GalNAco-(1-->4,6)-alpha-Gal-(1-->6)-alpha-Gal-(1-->3)-alpha-Gal-(1-P-3)-alpha-DDHep-(1-->5)-alpha-8-aminoKdo4R-(2-->6)-beta-GlcN4P-(1-->6)-alpha-GlcN1P, where R is P or EtNPP. There are several novel aspects to this LPS. It contains a novel linking unit between the core polysaccharide and lipid A moieties, namely 8-amino-3,8-dideoxy-D-manno-octulosonic acid (8-aminoKdo) and a residue of 2-acetamido-2-deoxy-D-galactose (N-acetylgalactosamine, GalNAco) in an open-chain form, linked as cyclic acetal to O-4 and O-6 of D-galactopyranose. The structure contains a phosphodiester linkage between the alpha-D-galactopyranose and D-glycero-D-manno-heptose (DDHep) residues.

Amination↗

PubMed2003

Structural profiling of lipopolysaccharide glycoforms expressed by non-typeable Haemophilus influenzae: phenotypic similarities between NTHi strain 162 and the genome strain Rd.

Non-typeable Haemophilus influenzae (NTHi) is a significant cause of otitis media in children. We have employed single and multiple step electrospray ionization mass spectrometry (ESIMS) and NMR spectroscopy to profile and elucidate lipopolysaccharide (LPS) structural types expressed by NTHi strain 162, a strain obtained from an epidemiological study in Finland. ESIMS on O-deacylated LPS (LPS-OH) and core oligosaccharide (OS) samples of LPS provided information on the composition and relative abundance of glycoforms differing in the number of hexoses linked to the conserved inner-core element, L-alpha-D-Hepp-(1-->2)-[PEtn-->6]-L-alpha-D-Hepp-(1-->3)-L-alpha-D-Hepp-(1-->5)-[PPEtn-->4]-alpha-Kdop-(2-->6)-Lipid A of H. influenzae LPS. The strain examined was found to elaborate Hex2 to Hex5 LPS glycoform populations having structures identical to those observed for H. influenzae strain Rd [Risberg, A.; Masoud, H.; Martin, A.; Richards, J.C.; Moxon, E.R.; Schweda, E.K.H. Eur. J. Biochem. 1999, 261, 171-180], the strain for which the complete genome has been sequenced. In addition, sialyllactose-containing glycoforms previously identified in strain Rd as well as several NTHi strains, were identified as minor components. Multiple step tandem ESIMS (MS(n)) on dephosphorylated and permethylated OS provided information on the arrangement of glycoses within the major population of glycoforms and on the existence of additional isomeric glycoforms. Minor Hex1 and Hex6 glycoforms were detected and characterized where the Hex6 glycoform was comprised of a dihexosamine-containing pentasaccharide chain attached at the proximal heptose residue of the inner-core unit. LPS structural motifs present in the NTHi strain 162 are expressed by a genetically diverse set of disease causing isolates, providing the basis for a vaccine strategy against NTHi otitis media.

Carbohydrate Conformation↗

PubMed1997

Lipo-oligosaccharides of Campylobacter jejuni serotype O:10. Structures of core oligosaccharide regions from a bacterial isolate from a patient with the Miller-Fisher syndrome and from the serotype reference strain.

Lipo-oligosaccharide (LOSa) was obtained by phenol-water extraction of bacterial cells of an isolate PG 836, identified as Campylobacter jejuni serotype O:10, from a patient who subsequently developed the Miller-Fisher syndrome (MFS). The product was separated into a water-insoluble gel of low Mr and a water-soluble component of high Mr. The structure of the core oligosaccharide region in LOSa is reported herein for comparison with LOSb from the C. jejuni O:10 reference strain, and is based on investigations carried out on: (1) O-deacylated LOSa; (2) the core oligosaccharide (OS 1a) liberated on acetic acid hydrolysis of the ketosidic linkages to lipid A, with accompanying loss of N-acetylneuraminic acid residues; (3) the product of the removal of phosphate residues from OS 1a to give OS 2a; and (4) the Smith degradation of OS 2a to yield a mixture of Os 3a and OS 4a. The results revealed that the core oligosaccharide region in LOSa from the MFS bacterial isolate had chains (1a), of which some were terminated by an N-acetylneuraminobiose [Neu5Ac(alpha 2-8)Neu5Ac] unit in a GD3 [Neu5Ac-Neu5Ac-Gal] epitope, and the inner regions of which were different from those of other C. jejuni serotypes. Similar experiments on LOSb from bacterial cells of the C. jejuni O:10 reference strain showed that the core oligosaccharide unit [1a, R = P (phosphoric monoester)] of LOSa from the MFS isolate was more uniformly complete than that of the O:10 reference strain [1b, R = AEP (2-aminoethylphosphate)] differing in the nature of the phosphate substituent at the inner heptose residue. The close structural relationship of LOSa from the MFS associated bacterium to LOSb from the O:10 reference strain runs parallel to that of the previously studied Guillain-Barré syndrome (GBS) associated bacterium typed as C. jejuni O:19 in comparison with the lipo-oligosaccharide from the reference strain. Preliminary studies on the high Mr components showed that those from the O:10 strains were indistinguishable from each other, but were structurally unrelated to those from the GBS associated C. jejuni serotype O:19 isolates and the O:19 reference strain [G.O. Aspinall, A.G. McDonald, and H. Pang, Biochemistry, 33 (1994) 250-255].

Campylobacter jejuni↗

PubMed1998

The lipooligosaccharide (LOS) of Neisseria meningitidis serogroup B strain NMB contains L2, L3, and novel oligosaccharides, and lacks the lipid-A 4'-phosphate substituent.

The complete structure of the lipooligosaccharide (LOS) from Neisseria meningitidis strain NMB (serotype 2b:P1.2,5), a serogroup B cerebrospinal fluid isolate, was determined. Two oligosaccharide (OS) fractions and lipid-A were obtained following mild acid hydrolysis of the LOS. The structures in these fractions were determined using glycosyl composition and linkage analyses, N spectroscopy and mass spectrometry. One oligosaccharide fraction (OS1) consists of a molecule having a glycosyl sequence identical to that previously reported for the LOS from immunotype L2 N. meningitidis [A. Gamain, M. Beurret, F. Michon, J.-R. Brisson, and H.J. Jennings, J. Biol. Chem.,267,(112) 922-925] i.e., a lacto-N-neotetraose is attached to heptose I (Hep I), with terminally linked N-acetylglucosaminosyl and glucosyl residues attached to Hep II of the inner core. Approximately 70% of this structure is acetylated at O-6 of the terminally linked alpha-N-acetyl-glucosaminosyl residue. As with the L2 structure, the NMB LOS contained phosphoethanolamine (PEA) at O-6 or O-7 of the Hep II residue. The second oligosaccharide fraction (OS2) contains a a mixture of three different molecules, all of which vary from one another in their glycosyl substitution patterns of the Hep II residue. The most abundant molecule in OS2 has a structure identical to that of OSI, i.e., it has the L2 glycosyl sequence. A second molecule (OS2a) lacks the terminal glucosyl residue at O-3 of Hep II; i.e., it has a glycosyl sequence identical to that of the mild acid released oligosaccharide of N. meningitidis immunotype L3, L4, or L7 LOSs. The third molecule (OS2b) is a novel structure that lacks the terminal N-acetylglucosaminosyl residue linked to O-2 of Hep II. Overall, 76% of OS released from NMB LOS has the L2 structure, 15% is OS2a (L3), and 9% is OS2b. A portion (20%) of the molecules in the NMB LOS preparation also contained terminally linked sialic acid attached to O-3 of the lacto-N-neotetraose galactosyl residue, which is also consistent with the L3, or L4 LOS structures. In contrast to the previously reported structure of N. meningitidis lipid-A [V. A. Kulshin, U. Zähringer, B. Linder, C.E. Frasch, C-M. Tsai, B.A. Dmitriev, and E.T Rietschel, J. Bacteriol., 174, (1992)1793-1800], only 30% of the lipid-A from NMB LOS possesses 4'-phosphate. Comparison with the lipid-A of LOS purified from an isogenic acapsulate mutant, M7, revealed that the 4'-position was almost completely occupied with phosphate. These data emphasize the structural heterogeneity of the OS and phosphate substituents of Hep II, and 4'-phosphorylation of lipid-A of meningococcal LOS.

Carbohydrate Sequence↗

PubMed1999

Synthesis of Pseudomonas aeruginosa lipopolysaccharide core antigens containing 7-O-carbamoyl-L-glycero-alpha-D-manno-heptopyranosyl residues.

The monosaccharide allyl 7-O-carbamoyl-L-glycero-alpha-D-manno- heptopyranoside, the reducing disaccharide 7-O-carbamoyl-L-glycero-alpha-D- manno-heptopyranosyl-(1-->3)-L-glycero-D-manno-heptopyranose and the disaccharides allyl 7-O-carbamoyl-L-glycero-alpha-D-manno-heptopyranosyl-(1-->3)-L-glycero- beta- and alpha-D-manno-heptopyranoside were prepared in good yields. The 7-O-carbamoyl substituent was regioselectively introduced via NH3-NH4HCO3 treatment of a 6,7-O-carbonate group. Glycosylation steps were carried out using Me3SiOTf or BF3.Et2O promoted coupling of allyl alcohol with trichloroacetimidate or fluoride glycosyl donors, respectively. The deprotected allyl glycosides were reacted with cysteamine to afford spacer glycosides which were subsequently linked to bovine serum albumin. The artificial antigens which are related to the dephosphorylated heptose region of the lipopolysaccharide core region from Pseudomonas aeruginosa classified into RNA group I may be used for the characterization of monoclonal antibodies directed against inner core epitopes of human-pathogenic Pseudomonas species.

Carbohydrate Conformation↗

PubMed1999

Chemical structure of a polysaccharide from Campylobacter jejuni 176.83 (serotype O:41) containing only furanose sugars.

A neutral polysaccharide was obtained by hot phenol-water extraction of biomass from Campylobacter jejuni 176.83 and subsequently separated from acid-liberated core oligosaccharide of lipopolysaccharide by sequential GPC on Bio-Gel P6 and TSK-40 columns. All sugar components of the trisaccharide repeating unit of the polysaccharide were found to be of the furanose ring form. The major trisaccharide contained beta-L-arabinose, 6-deoxy-beta-D-altro-heptose (beta-D-6d-altHep) and 6-deoxy-beta-L-altrose (beta-L-6d-Alt), whereas in the minor trisaccharide the beta-L-6d-Alt is replaced by its C-5 epimer alpha-D-Fuc. On the basis of 1H and 13C NMR spectroscopic studies, including 2D ROESY, HMQC and HMQC-TOCSY experiments, the following structures of the repeating units were established: [formula: see text]

Campylobacter jejuni↗

PubMed1984

Capillary gas chromatography-mass spectrometry of carbohydrate components of legionellae and other bacteria.

Capillary gas chromatography using fused-silica columns followed by electron impact or chemical ionization mass spectrometry was used to profile and identify neutral and amino sugars present in several legionellae and other bacteria. A modified alditol acetate derivatization method was employed to produce volatile carbohydrate derivatives. Muramic acid, a component of bacterial peptidoglycan, was detected in all legionellae examined. Heptose, a component of bacterial lipopolysaccharide, was identified in Escherichia coli organisms and in several purified Gram-negative bacterial lipopolysaccharides but not in the legionellae examined. Two amino dideoxyhexoses were found to be present in several of the Legionellae examined. The potential of gas chromatography-mass spectrometry for the direct chemical characterization of microorganisms is discussed.

Amino Sugars↗

PubMed1998

Cloning, sequencing, and characterization of the lipopolysaccharide biosynthetic enzyme heptosyltransferase I gene (waaC) from Campylobacter jejuni and Campylobacter coli.

Campylobacter jejuni and Campylobacter coli are common causes of gastrointestinal disease and a proportion of C. jejuni infections have been shown to be associated with the Guillain-Barré syndrome. The waaC gene from Campylobacter coli, involved in lipopolysaccharide core biosynthesis, was cloned by complementation of a heptose-deficient strain of Salmonella typhimurium, as judged by novobiocin sensitivity, lipopolysaccharide (LPS)-specific phage sensitivity, and polyacrylamide-resolved lipopolysaccharide profiles. The C. jejuni waaC gene was subsequently cloned using the waaC gene isolated from C. coli as a probe. The C. jejuni and C. coli waaC genes are capable of encoding proteins of 342 amino acids with calculated molecular masses of 39381Da and 39317Da, respectively. Sequence and in-vitro analyses suggested that the C. coli waaC gene may be transcribed from its own promoter. Translation of the C. coli waaC gene in a cell-free system yielded a protein with a Mr of 39000. The waaC gene was detected in every C. jejuni and C. coli isolate tested as judged by dot-blot hybridization analysis. Southern hybridization analysis indicated that both Campylobacter species contain a single copy of the waaC gene. Unlike Escherichia coli and S. typhimurium isolates, the waaC gene in C. jejuni and C. coli isolates does not appear to be linked to the waaF (rfaF) gene.

Base Sequence↗