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1. (Article ID: 1179)
Schweda EK, Li J, Moxon ER, Richards JC
Structural analysis of lipopolysaccharide oligosaccharide epitopes expressed by non-typeable Haemophilus influenzae strain 176
Carbohydrate Research 337(5) (2002)
409-420
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-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-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 [Mansson, 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):
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, Phosphocholine, 5-N-Acetylneuraminic acid, CE-ESIMS/MS
NCBI PubMed ID: 11861015Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: elke.schweda
kfc.ki.se
Institutions: Clinical Research Centre, Karolinska Institutet and University College of South Stockholm, NOVUM, S-141 86, Huddinge, Sweden
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, HF solvolysis, sugar analysis, mild acid hydrolysis, de-O-acetylation, NMR-1D, CE-ESI-MS/MS
The publication contains the following compound(s):
- Compound ID: 3213
|
b-D-Glcp-(1-4)-+
|
Cho-(1--P--6)--b-D-Glcp-(1-4)-+
|
?%Gly-(2-?)-+ EtN-(1--P--6)--+ | EtN-(1---P---P---4)-+
| | | |
b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
- Compound ID: 3214
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
|
?%Gly-(2-?)-+ EtN-(1--P--6)--+ | EtN-(1---P---P---4)-+
| | | |
b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
- Compound ID: 3215
|
b-D-Glcp-(1-4)-+
|
Cho-(1--P--6)--b-D-Glcp-(1-4)-+
|
EtN-(1--P--6)--+ | EtN-(1---P---P---4)-+
| | |
?%Gly-(2-?)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
- Compound ID: 3216
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
|
EtN-(1--P--6)--+ | EtN-(1---P---P---4)-+
| | |
?%Gly-(2-?)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
a-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
- Compound ID: 3217
|
b-D-Glcp-(1-4)-+
|
Cho-(1--P--6)--b-D-Glcp-(1-4)-+
|
?%Gly-(2-?)-+ EtN-(1--P--6)--+ |
| | |
b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Sug
Sug = anhKdo-ol |
Show graphically |
Structure type: oligomer
Trivial name: glycoform
Compound class: core oligosaccharide
- Compound ID: 3218
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
|
?%Gly-(2-?)-+ EtN-(1--P--6)--+ |
| | |
b-D-Galp-(1-3)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Sug
|
a-D-Glcp-(1-3)-+
Sug = anhKdo-ol |
Show graphically |
Structure type: oligomer
Trivial name: glycoform
Compound class: core oligosaccharide
- Compound ID: 3219
|
b-D-Glcp-(1-4)-+
|
Cho-(1--P--6)--b-D-Glcp-(1-4)-+
|
EtN-(1--P--6)--+ |
| |
?%Gly-(2-?)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Sug
Sug = anhKdo-ol |
Show graphically |
Structure type: oligomer
Trivial name: glycoform
Compound class: core oligosaccharide
- Compound ID: 3220
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
|
EtN-(1--P--6)--+ |
| |
?%Gly-(2-?)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Sug
|
a-D-Glcp-(1-3)-+
Sug = anhKdo-ol |
Show graphically |
Structure type: oligomer
Trivial name: glycoform
Compound class: core oligosaccharide
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