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1. (Article ID: 1929)
DiFabio JL, Michon F, Brisson JR, Jennings HJ
Structure of the L1 and L6 core oligosaccharide epitopes of Neisseria meningitidis
Canadian Journal of Chemistry 68(7) (1990)
1029-1034
The core oligosaccharides obtained from the lipopolysaccharides of Neisseria menirlgitidis serotypes 1 and 6 were isolated by mild acid hydrolysis, and their structures elucidated by combined chemical, biochemical, and physical techniques. Use was made of 500 MHz 'H nuclear magnetic resonance measurements in both one-dimensional and two-dimensional modes as well as of nuclear Overhauser enhancement experiments. To assist in the structural assignments, the purified oligosaccharides were also degraded by chemical and enzymatic procedures to smaller fragments. The L1 oligosaccharide is a biantennary partially O-acetylated heptasaccharide in which the larger antenna terminates in a a-D-Galp1--4b-D-Galp1--4b-D-Glcp unit, whereas the smallest disaccharide antenna carries phosphorylethanolamine groups at O-3 of its heptosyl moiety. The L6 oligosaccharide is also a biantennary partially O-acetylated heptasaccharide but, unlike the L1 core, is terminated by a b-D-GlcpNAc1--3b-D-Galp1--4b-D-Glcp unit in its larger antenna. The heptosyl moiety in the small disaccharide antenna bears a phosphorylethanolamine group at O-7, unlike O-3 for the L1 determinant.
lipopolysaccharides, structure, Neisseria meningitidis, NMR spectroscopy, oligosaccharide epitopes
Publication DOI: 10.1139/v90-160Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ont., Canada KIA OR6
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, gel filtration, sugar analysis, dephosphorylation, GLC, de-O-acetylation, enzymatic digestion, optical rotation measurement
The publication contains the following compound(s):
- Compound ID: 4981
|
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
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a-D-GlcpNAc-(1-2)-+ |
| |
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo |
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Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G37862WI
- Compound ID: 4982
|
a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-Kdo |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G38725QX, GlycomeDB:
37944
- Compound ID: 4985
|
b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
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a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G96659YT, GlycomeDB:
37946
- Compound ID: 4983
|
b-D-GalpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
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a-D-GlcpNAc-(1-2)-+ |
| |
EtN-(1--P--7)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G06919WT
- Compound ID: 4984
|
a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-+
|
b-D-GalpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-Kdo |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G06471PS, GlycomeDB:
37945
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