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1. (Article ID: 262)
Holst O
On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides
Polish Journal of Chemistry 73 (1999)
1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
The publication contains the following compound(s):
- Compound ID: 917
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a-Hepp-(1-2)-a-Hepp-(1-3)-+ P-4)-+
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Subst-(1-?)-b-D-Galp-(1-7)-a-Hepp-(1-6)-a-Hepp-(1-6)-b-D-Glcp-(1-4)-a-Hepp-(1-5)-a-Kdop-(2--/lipid A/
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b-D-Glcp-(1-6)-+
Subst = O-antigen |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 919
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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Subst-(1-7)-+ | P-7)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-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/
Subst = O-antigen |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 910
Structure type: oligomer
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G40966ZH
- Compound ID: 907
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?%a-Kdop-(2-4)-a-Kdop-(2-4)-+
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?%b-D-GalpA-(1-6)-b-D-Glcp-(1-4)-+ |
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L-gro-a-D-manHepp-(1-7)-+ | |
| | |
?%D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-?%D-gro-a-D-manHepp-(1-6)-a-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-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: core oligosaccharide
Reference(s) to other database(s): GTC:G69530NW
- Compound ID: 908
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a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-+
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b-D-GalpA-(1-7)-L-gro-a-D-manHepp-(1-7)-+ |
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a-D-Glcp-(1-2)-+ | |
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D-gro-a-D-manHepp-(1-6)-b-D-GlcpN-(1-4)-a-D-GalpA-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
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EtN-(1-0)-?%P-6)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G39365IF
- Compound ID: 909
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?%P-7)-D-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-7)-+
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b-D-Glcp-(1-3)-+ | b-D-Glcp-(1-4)-+ a-Kdop-(2-4)-+
| | | |
b-D-Glcp-(1-6)-a-D-GalpNAc-(1-6)-a-D-Galp-(1-4)-a-D-GalpNAc-(1-3)-b-D-FucpNAc-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
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b-D-Glcp-(1-2)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G28330BR
- Compound ID: 912
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EtN-(1--P--7)--+
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a-L-Rhap-(1-4)-a-D-Glcp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ | P-4)-+
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R-3HOBut-(1-4)-a-D-Fucp4N-(1-4)-a-Legp5Ac7Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/
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EtN-(1--P--2)--+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 913
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a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-3)-+
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b-D-Galp-(1-4)-+ |
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D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1--/lipid A/
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L-gro-a-D-manHepp-(1-6)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide, LPS
Reference(s) to other database(s): GTC:G61727JL, GlycomeDB:
16916
- Compound ID: 914
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-?)-+
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b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G48285OL
- Compound ID: 915
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-?)-+
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a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G67282CN
- Compound ID: 916
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L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ P-?)-+
| |
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G60554EK
- Compound ID: 918
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Subst-(1-7)-D-gro-a-D-manHepp-(1-2)-+ P-7)-+
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-D-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/
Subst = O-antigen |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 920
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-+ | P-7)-+
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D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-2)-D-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: core oligosaccharide
Reference(s) to other database(s): GTC:G89440XD
- Compound ID: 921
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-+ | P-7)-+
| | |
Subst-(1-3)-b-D-Galp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-2)-D-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/
Subst = Lewis (y) antigen |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
- Compound ID: 922
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a-Kdop-(2-4)-a-Kdop-(2-4)-+
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a-D-Manp-(1-?)-+ |
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a-D-Manp-(1-2)-D-gro-a-D-manHepp-(1-?)-D-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: fragment of a bigger structure
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G86940HN
- Compound ID: 923
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D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-4)-+
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L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G40414RW
- Compound ID: 924
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D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-4)-+
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L-gro-a-D-manHepp-(1-7)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-?)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G95578SU
- Compound ID: 925
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D-gro-a-D-manHepp-(1-5)-+
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a-D-GalpA-(1-4)-a-D-GalpA-(1-4)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G39786NK
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2. (Article ID: 2381)
Michon F, Shaw DH, Banoub JH
Structure of the lipopolysaccharide core isolated from a human strain of Aeromonas hydrophila
European Journal of Biochemistry 145 (1984)
107-114
Lipopolysaccharide was isolated from the cell-walls of a human strain of Aeromonas hydrophila by the aqueous phenol method in 0.58% yield (based on dry weight of bacteria). The lipopolysaccharide consisted of SR-polysaccharide, core-oligosaccharide and lipid A; there was no O-specific polysaccharide. The core had the composition D-galactose, D-glucose, D-glycero-D-manno-heptose, L-glycero-D-manno-heptose and D-glucosamine in a molar ratio of 1:1:2:4:1. Glucosamine was linked to an L-glycero-D-manno-heptose residue by a bond which was resistant to hydrolysis. The D-glucosamine-(1→7)-LD-heptose disaccharide was isolated and identified by the mass spectrum of its methylated alditol and the heptose residue not observed under normal hydrolysis conditions was easily determined after deamination of the complete core. Methylation analysis, chemical degradation, periodate and chromium trioxide oxidations and nuclear magnetic resonance (13C and 1H NMR) spectroscopy were used to identify the structure of the core oligosaccharide as: (formula: see text)
NCBI PubMed ID: 6489347Publication DOI: 10.1111/j.1432-1033.1984.tb08528.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Fisheries Research Branch, Northwest‐Atlantic Fisheries Centre, P. O. Box 5667, St John's, Newfoundland, Canada
Methods: 13C NMR, 1H NMR, GC-MS
The publication contains the following compound(s):
- Compound ID: 913
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a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-3)-+
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b-D-Galp-(1-4)-+ |
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D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1--/lipid A/
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L-gro-a-D-manHepp-(1-6)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide, LPS
Reference(s) to other database(s): GTC:G61727JL, GlycomeDB:
16916
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