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1. (CSDB ID: 9371) | report error |
| a-D-Glcp-(1-2)-b-D-Glcp-(1-2)-+ | a-D-GalpNAc-(1-2)-+ | | | a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-3)-a-D-QuipNAc4NAc-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-4)-a-D-GalpNAcA6NH2-(1-3)-b-D-QuipNAc4NAc-(1-4)-b-D-Manp-(1-4)-a-D-Manp-(1-5)-Kdo | a-D-Glcp-(1-3)-+ | Show graphically |
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Francisella novicida U112
(NCBI TaxID 401614,
species name lookup)
]
nrc-cnrc.gc.caFrancisella novicida (U112), a close relative of the highly virulent bacterium F. tularensis, is known to produce a lipopolysaccharide that is significantly different in biological properties from the LPS of F. tularensis. Here we present the results of the structural analysis of the F. novicida LPS core part, which is found to be similar to that of F. tularensis, differing only by one additional α-Glc residue:where R is an O-chain, linked via a β-bacillosamine (2,4-diamino-2,4,6-trideoxyglucose) residue. The lipid part of F. novicida LPS contains no phosphate substituent and apparently has a free reducing end, a feature also noted in F. tularensis LPS.
LPS, core structure, Francisella, Francisella novicida
Structure type: oligomer13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 5,2,2 aDGlcp 98.8 72.8 73.9 70.8 73.1 61.9 5,2 bDGlcp 101.8 77.7 75.7 71.0 77.0 62.0 5,4,2,2 Ac 5,4,2 aDGalpN 95.8 51.3 69.2 69.9 72.7 62.7 5,4,3 aDGlcp 103.4 73.3 75.1 71.5 74.0 62.6 5,4,4,3,4,4,4,3,4,4,2 Ac 5,4,4,3,4,4,4,3,4,4,6 NH2 5,4,4,3,4,4,4,3,4,4 aDGalpNA 5,4,4,3,4,4,4,3,4,2 Ac 5,4,4,3,4,4,4,3,4,6 NH2 5,4,4,3,4,4,4,3,4 aDGalpNA 5,4,4,3,4,4,4,3,2 Ac 5,4,4,3,4,4,4,3,6 NH2 5,4,4,3,4,4,4,3 aDGalpNA 5,4,4,3,4,4,4,2 Ac 5,4,4,3,4,4,4,4 Ac 5,4,4,3,4,4,4 aDQuipN4N 99.6 53.9 75.4 58.2 68.8 17.6 5,4,4,3,4,4,2 Ac 5,4,4,3,4,4,6 NH2 5,4,4,3,4,4 aDGalpNA 5,4,4,3,4,2 Ac 5,4,4,3,4,6 NH2 5,4,4,3,4 aDGalpNA 5,4,4,3,2 Ac 5,4,4,3,6 NH2 5,4,4,3 aDGalpNA 5,4,4,2 Ac 5,4,4,4 Ac 5,4,4 bDQuipN4N ? ? ? 58.5 72.4 17.9 5,4 bDManp 100.8 73.1 83.3 72.3 77.2 61.1 5 aDManp 99.8 77.7 69.8 77.6 73.2 61.2 ?XKdo? ? 97.2 35.5 66.9 77.5 72.7 70.6 64.4 1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 5,2,2 aDGlcp 5.41 3.55 3.74 3.45 4.05 3.78-3.82 5,2 bDGlcp 4.69 3.52 3.61 3.45 3.51 3.75-3.93 5,4,2,2 Ac 5,4,2 aDGalpN 5.52 4.20 3.95 3.97 4.11 3.69-3.74 5,4,3 aDGlcp 5.08 3.48 3.55 3.33 4.04 3.70-3.91 5,4,4,3,4,4,4,3,4,4,2 Ac 5,4,4,3,4,4,4,3,4,4,6 NH2 5,4,4,3,4,4,4,3,4,4 aDGalpNA 5,4,4,3,4,4,4,3,4,2 Ac 5,4,4,3,4,4,4,3,4,6 NH2 5,4,4,3,4,4,4,3,4 aDGalpNA 5,4,4,3,4,4,4,3,2 Ac 5,4,4,3,4,4,4,3,6 NH2 5,4,4,3,4,4,4,3 aDGalpNA 5,4,4,3,4,4,4,2 Ac 5,4,4,3,4,4,4,4 Ac 5,4,4,3,4,4,4 aDQuipN4N 4.91 4.08 3.98 3.79 4.20 1.07 5,4,4,3,4,4,2 Ac 5,4,4,3,4,4,6 NH2 5,4,4,3,4,4 aDGalpNA 5,4,4,3,4,2 Ac 5,4,4,3,4,6 NH2 5,4,4,3,4 aDGalpNA 5,4,4,3,2 Ac 5,4,4,3,6 NH2 5,4,4,3 aDGalpNA 5,4,4,2 Ac 5,4,4,4 Ac 5,4,4 bDQuipN4N ? ? 3.98 3.72 3.54 1.23 5,4 bDManp 4.86 4.37 3.90 4.16 3.50 3.69-3.95 5 aDManp 5.22 4.32 4.03 3.90 4.03 3.76-3.76 ?XKdo? - - 1.92-2.00 4.16 4.14 3.92 3.74 3.63-3.80 1H/13C HSQC data: Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 5,2,2 aDGlcp 98.8/5.41 72.8/3.55 73.9/3.74 70.8/3.45 73.1/4.05 61.9/3.78-3.82 5,2 bDGlcp 101.8/4.69 77.7/3.52 75.7/3.61 71.0/3.45 77.0/3.51 62.0/3.75-3.93 5,4,2,2 Ac 5,4,2 aDGalpN 95.8/5.52 51.3/4.20 69.2/3.95 69.9/3.97 72.7/4.11 62.7/3.69-3.74 5,4,3 aDGlcp 103.4/5.08 73.3/3.48 75.1/3.55 71.5/3.33 74.0/4.04 62.6/3.70-3.91 5,4,4,3,4,4,4,3,4,4,2 Ac 5,4,4,3,4,4,4,3,4,4,6 NH2 5,4,4,3,4,4,4,3,4,4 aDGalpNA 5,4,4,3,4,4,4,3,4,2 Ac 5,4,4,3,4,4,4,3,4,6 NH2 5,4,4,3,4,4,4,3,4 aDGalpNA 5,4,4,3,4,4,4,3,2 Ac 5,4,4,3,4,4,4,3,6 NH2 5,4,4,3,4,4,4,3 aDGalpNA 5,4,4,3,4,4,4,2 Ac 5,4,4,3,4,4,4,4 Ac 5,4,4,3,4,4,4 aDQuipN4N 99.6/4.91 53.9/4.08 75.4/3.98 58.2/3.79 68.8/4.20 17.6/1.07 5,4,4,3,4,4,2 Ac 5,4,4,3,4,4,6 NH2 5,4,4,3,4,4 aDGalpNA 5,4,4,3,4,2 Ac 5,4,4,3,4,6 NH2 5,4,4,3,4 aDGalpNA 5,4,4,3,2 Ac 5,4,4,3,6 NH2 5,4,4,3 aDGalpNA 5,4,4,2 Ac 5,4,4,4 Ac 5,4,4 bDQuipN4N ?/? ?/? ?/3.98 58.5/3.72 72.4/3.54 17.9/1.23 5,4 bDManp 100.8/4.86 73.1/4.37 83.3/3.90 72.3/4.16 77.2/3.50 61.1/3.69-3.95 5 aDManp 99.8/5.22 77.7/4.32 69.8/4.03 77.6/3.90 73.2/4.03 61.2/3.76-3.76 ?XKdo? 35.5/1.92-2.00 66.9/4.16 77.5/4.14 72.7/3.92 70.6/3.74 64.4/3.63-3.80
1H NMR data:
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13C NMR data:
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The spectrum also has 4 signals at unknown positions (not plotted). |
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2. (CSDB ID: 23826) | report error |
| ?%a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-7)-+ | a-D-Galp-(1-2)-a-D-Galp-(1-2)-+ | ?%EtN-(1-0)-?%P-4)-+ | | | a-L-AltpNAcA-(1-3)-b-D-FucpNAc4N-(1-4)-a-L-AltpNAcA-(1-3)-b-D-FucpNAc4N-(1-3)-b-D-Glcp-(1-3)-a-D-Glcp-(1-3)-a-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo | P-4)-+ | Show graphically |
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Shigella sonnei 53G
(NCBI TaxID 216599,
species name lookup)
, ICD11: SA56 , ICD11: XN7HG ]; infection due to Shigella sonnei [ICD11: XN9M9 ]mail.nih.govShigellosis, an enteric disease, is on the World Health Organization's priority prevention list. In one study, the Shigella sonnei O-specific polysaccharide (O-SP)-protein conjugate showed 72% protection against disease in Israeli army recruits exposed to high rates (8-14%) of infection. The protection was related to vaccine-induced IgG anti-O-SP levels. Synthetic oligosaccharides of Shigella dysenteriae type 1, bound by their reducing ends to a carrier protein ('sun'-type configuration), induced significantly higher antibody levels than the native O-SP bound to protein by multiple-point attachments ('lattice'-type configuration). Attempts to synthesize the S. sonnei O-SP based oligosaccharides were not successful. Here, we describe the isolation, characterization, and conjugation of low-molecular-mass O-SP-core (O-SPC) fragments. The O-SPC fragments were bound by their reducing ends similar to the preparation of the synthetic S. dysenteriae type 1 conjugates. The O-SPC conjugates used oxime linkages between the terminal Kdo residues at the reducing ends of the S. sonnei saccharides and aminooxy linkers bound to BSA or a recombinant diphtheria toxin. The coupling reaction was carried out at a neutral pH and room temperature. IgG antibody levels induced in young outbred mice by the S. sonnei O-SPC conjugates were significantly higher then those elicited by the O-SP conjugates. Accordingly, we propose to evaluate clinically these conjugates.
Lipopolysaccharide, Kdo, IgG, vaccine, glycoconjugate
Structure type: oligomer13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 5,3,3,3,2,2 aDGalp 96.7 69.4 70.5 70.5 72.5 ? 5,3,3,3,2 aDGalp 92.5 73.5 69.3 70.4 72.4 ? 5,3,3,3,3,3,3,4,3,2 Ac 5,3,3,3,3,3,3,4,3 aLAltpNA 102.1 52.5 69.1 69.9 78.4 175.1 5,3,3,3,3,3,3,4,2 Ac 5,3,3,3,3,3,3,4 bDFucpN4N 104.2 52.1 77.0 56.1 68.3 16.7 5,3,3,3,3,3,3,2 Ac 5,3,3,3,3,3,3 aLAltpNA 102.3 52.4 68.9 78.3 78.1 174.7 5,3,3,3,3,3,2 Ac 5,3,3,3,3,3 bDFucpN4N 102.8 52.6 77.0 55.9 68.3 16.7 5,3,3,3,3 bDGlcp 103.7 74.0 85.4 69.3 76.7 61.4 5,3,3,3 aDGlcp 95.7 73.8 79.0 69.0 72.5 62.3 5,3,3 aDGlcp 101.6 71.6 77.4 71.6 73.4 ? 5,3,4 P 5,3,7,7 %aDGlcpN 5,3,7 aXLDmanHepp 5,3 aXLDmanHepp 5,4,0 %xXEtN 5,4 %xXP? 5 aXLDmanHepp ?XKdo? 1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 5,3,3,3,2,2 aDGalp 5.33 3.86 3.98 4.00 4.12 ? 5,3,3,3,2 aDGalp 5.62 3.99 4.21 4.01 4.13 ? 5,3,3,3,3,3,3,4,3,2 Ac 5,3,3,3,3,3,3,4,3 aLAltpNA 4.90 4.00 3.69 4.40 4.52 - 5,3,3,3,3,3,3,4,2 Ac 5,3,3,3,3,3,3,4 bDFucpN4N 4.76 3.88 4.19 3.96 4.08 1.34 5,3,3,3,3,3,3,2 Ac 5,3,3,3,3,3,3 aLAltpNA 4.79 3.84 3.76 4.47 4.60 - 5,3,3,3,3,3,2 Ac 5,3,3,3,3,3 bDFucpN4N 4.77 3.84 4.19 3.86 4.08 1.34 5,3,3,3,3 bDGlcp 4.74 3.40 3.70 3.50 3.45 3.78-3.90 5,3,3,3 aDGlcp 5.83 3.89 4.19 3.58 4.13 3.75-3.75 5,3,3 aDGlcp 5.28 3.68 4.06 3.79 3.86 ? 5,3,4 P 5,3,7,7 %aDGlcpN 5,3,7 aXLDmanHepp 5,3 aXLDmanHepp 5,4,0 %xXEtN 5,4 %xXP? 5 aXLDmanHepp ?XKdo? 1H/13C HSQC data: Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 5,3,3,3,2,2 aDGalp 96.7/5.33 69.4/3.86 70.5/3.98 70.5/4.00 72.5/4.12 ?/? 5,3,3,3,2 aDGalp 92.5/5.62 73.5/3.99 69.3/4.21 70.4/4.01 72.4/4.13 ?/? 5,3,3,3,3,3,3,4,3,2 Ac 5,3,3,3,3,3,3,4,3 aLAltpNA 102.1/4.90 52.5/4.00 69.1/3.69 69.9/4.40 78.4/4.52 5,3,3,3,3,3,3,4,2 Ac 5,3,3,3,3,3,3,4 bDFucpN4N 104.2/4.76 52.1/3.88 77.0/4.19 56.1/3.96 68.3/4.08 16.7/1.34 5,3,3,3,3,3,3,2 Ac 5,3,3,3,3,3,3 aLAltpNA 102.3/4.79 52.4/3.84 68.9/3.76 78.3/4.47 78.1/4.60 5,3,3,3,3,3,2 Ac 5,3,3,3,3,3 bDFucpN4N 102.8/4.77 52.6/3.84 77.0/4.19 55.9/3.86 68.3/4.08 16.7/1.34 5,3,3,3,3 bDGlcp 103.7/4.74 74.0/3.40 85.4/3.70 69.3/3.50 76.7/3.45 61.4/3.78-3.90 5,3,3,3 aDGlcp 95.7/5.83 73.8/3.89 79.0/4.19 69.0/3.58 72.5/4.13 62.3/3.75-3.75 5,3,3 aDGlcp 101.6/5.28 71.6/3.68 77.4/4.06 71.6/3.79 73.4/3.86 ?/? 5,3,4 P 5,3,7,7 %aDGlcpN 5,3,7 aXLDmanHepp 5,3 aXLDmanHepp 5,4,0 %xXEtN 5,4 %xXP? 5 aXLDmanHepp ?XKdo?
1H NMR data:
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13C NMR data:
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The spectrum also has 3 signals at unknown positions (not plotted). |
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3. (CSDB ID: 26683) | report error |
| a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-7)-+ | a-D-Galp-(1-2)-a-D-Galp-(1-2)-+ | P---P--4)-+ a-Kdop-(2-4)-+ | | | | a-L-AltpNAcA-(1-3)-b-D-FucpNAc4N-(1-4)-a-L-AltpNAcA-(1-3)-b-D-FucpNAc4N-(1-3)-b-D-Glcp-(1-3)-a-D-Glcp-(1-3)-a-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ | P-4)-+ | Show graphically |
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Shigella sonnei
(NCBI TaxID 624,
species name lookup)
]aok.pte.huThe structural variations in the rough-type endotoxins [lipopolysaccharides (LPSs)] of Shigella sonnei mutant strains (S. sonnei phase II-4303, R41, 562H and 4350) were investigated by Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) and tandem MS. A series of S. sonnei mutants had previously been the subject of analytical studies on the biosynthesis of heptose components in the core oligosaccharide region of LPSs. This study gives a complete overview on the structures of the full core and lipid A of S. sonnei mutant strains by MS. We found that the LPSs of the isogenic rough mutants were formed in a step-like manner containing 0:1:2:3 heptose in the deep core region of 4350, 562H, R41 and 4303, respectively, and the longest LPS from the mutant S. sonnei 4303 contained also five hexoses. The structural variations in the lipid A moiety and in the oligosaccharide part of the intact LPS were followed by MALDI-TOF-MS/MS. For the dissolution and the ionization of the samples, 2,5-dihydroxybenzoic acid in citric acid solution was applied as matrix. The detailed evaluation of the mass spectra indicates heterogeneity in the lipid part due to the differences in the phosphate and fatty acid composition.
lipopolysaccharide structure, MALDI-TOF/TOF-MS, Shigella sonnei rough mutant, MALDI-TOF-MS
Structure type: oligomer| New query | Export IDs | Home | Help |
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