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1. (Article ID: 5742)
Caroff M, Novikov A
Lipopolysaccharides: structure, function and bacterial identification
OCL - Oilseeds and fats, Crops and Lipids 27 (2020)
31
Lipopolysaccharides (LPS) are the main components of the outer membrane of Gram-negative bacteria. They are glycolipids containing a lipid moiety called lipid A, more often made of a bis-phosphorylated glucosamine disaccharide, carrying fatty acids in ester and amide linkages. Lipid A is linked to a core oligosaccharide of about 10 sugars, substituted in the wild-type strains, by long-chain oligosaccharide repetitive units, extending outside the bacteria and representing their main antigens. In addition to determine the serotype of the bacterium, LPS are highly potent biological molecules, capable of eliciting at the level of minute amounts, beneficial, as well as deleterious activities.
Lipopolysaccharide, serology, endotoxins, inflammation, structure-activity
Publication DOI: 10.1051/ocl/2020025Publisher: France: EDP Sciences (ISSN: 22726977, 22576614)
Correspondence: martine.caroff
lpsbiosciences.com
Institutions: LPS-BioSciences, Paris-Saclay University, Orsay, France, Hephaistos-Pharma, Paris-Saclay University, Orsay, France
The publication contains the following compound(s):
- Compound ID: 178
|
-2)-a-D-Rhap4NAc-(1-3)-a-L-Fucp-(1-4)-b-D-Glcp-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G60704LX, GlycomeDB:
3513
- Compound ID: 12432
|
R-3HOMyr-(1-2)-+
|
Lau-(1-3)-R-3HOMyr-(1-2)-+ |
| |
?%Myr-(1-3)-?%R-3HOMyr-(1-3)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ |
|
R-3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14447
|
Pam-(1-3)-R-3HOMyr-(1-2)-+ 3HOMyr-(1-2)-+
| |
EtN-(1---P---P---4)-b-D-GlcpN3N-(1-6)-/Variants 0/-EtN
| |
Pam-(1-3)-R-3HOMyr-(1-3)-+ 3HOMyr-(1-3)-+
/Variants 0/ is:
a-D-GlcpN-(1--P--1)--
OR (exclusively)
a-D-GlcpN3N-(1--P--1)-- |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 3920
|
EtN-(1--P--0)--?%P-4)-+
|
a-D-GlcpN-(1-7)-+ |
| |
a-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+ |
| |
a-D-GalpNA-(1-6)-+ | |
| | |
L-gro-a-D-manHepp-(1-4)-+ | | |
| | | |
a-D-GlcpNAc-(1-4)-b-D-ManpNAc3NAcA-(1-3)-b-L-FucpNAc4NMe-(1-6)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide, LPS
Reference(s) to other database(s): GTC:G45716UO
- Compound ID: 179
|
a-Neup5Ac-(2-6)-+
|
-6)-b-D-Galf-(1-3)-b-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G47888NW, GlycomeDB:
25535
- Compound ID: 14445
|
iPam-(1-3)-/Variants 0/-+ 3HOiMyr-(1-3)-+
| |
/Variants 1/-3HOiMyr-(1-3)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-P
| |
P-4)-+ /Variants 2/-+
/Variants 0/ is:
3HOSte-(1-2)-
OR (exclusively)
3HOBeh-(1-2)-
OR (exclusively)
3HOAch-(1-2)-
/Variants 1/ is:
Mon-(1-3)-
OR (exclusively)
27oxoMon-(1-3)-
/Variants 2/ is:
3HOSte-(1-2)-
OR (exclusively)
3HOBeh-(1-2)-
OR (exclusively)
3HOAch-(1-2)-
iPam = iso-hexadecanoic acid C16:0 (i16:0);
27oxoMon = 27-oxo-octacosanoic acid C28:0 |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14444
|
/Variants 0/-3HOMyr-(1-2)-+
|
Pam-(1-3)-3HOMyr-(1-3)-+ |
| |
Myr-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
?%a-D-GlcpN-(1--P--4)--+ |
|
?%a-D-GlcpN-(1--P--1)--+
/Variants 0/ is:
2HOMyr-(1-3)-
OR (exclusively)
2HOLau-(1-3)- |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14442
|
2HOLau-(1-3)-3HOLau-(1-2)-+
|
?%Pam-(1-3)-3HODco-(1-3)-+ |
| |
2HOLau-(1-3)-3HOLau-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1--P--0)--?%P-1)-EtN
| |
?%b-L-Arap4N-(1--P--4)--+ |
|
?%3HODco-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14454
|
2HOMyr-(1-3)-3HOMyr-(1-2)-+
|
Myr-(1-3)-3HOMyr-(1-2)-+ |
| |
?%b-L-Arap4N-(1--P--4)--b-D-GlcpN-(1-6)-a-D-GlcpN
| |
3HOMyr-(1-3)-+ |
|
?%b-L-Arap4N-(1--P--1)--+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14446
|
Pam-(1-3)-3HOPam-(1-3)-+
|
Pam-(1-3)-3HOPam-(1-3)-+ |
| |
Pam-(1-3)-3HOMyr-(1-2)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-P
| |
P-4)-+ 3HOLau-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14441
|
?%Pam-(1-3)-3HOMyr-(1-2)-+
|
?%b-L-Arap4N-(1--P--4)--+ |
| |
?%Myr-(1-3)-?%3HOMyr-(1-3)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1--P--0)--?%P-1)-EtN
| |
Lau-(1-3)-3HOMyr-(1-2)-+ |
|
?%3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14448
|
a-D-GlcpN-(1-7)-L-gro-a-D-manHepp-(1-7)-+
|
a-D-GlcpN-(1-3)-+ | P-4)-+ a-Kdop-(2-4)-+
| | | |
a-D-Glcp-(1-2)-a-D-Glcp-(1-2)-a-D-Galp-(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)-+ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G51714GC
- Compound ID: 9322
|
3HODco-(1-3)-+
|
?%a-D-GlcpN-(1--P--1)--+ |
| |
?%a-D-GlcpN-(1--P--4)--+ | |
| | |
Myr-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
3HOMyr-(1-3)-+ 3HOMyr-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 12654
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-FucpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G51475VE
- Compound ID: 14452
|
2HOMyr-(1-3)-3HOMyr-(1-2)-+
|
Myr-(1-3)-3HOMyr-(1-2)-+ |
| |
?%b-L-Arap4N-(1--P--4)--b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
?%3HOMyr-(1-3)-+ |
|
?%3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14453
|
?%3HOMyr-(1-3)-+
|
2HOPam-(1-3)-3HOMyr-(1-2)-+ |
| |
Myr-(1-3)-3HOMyr-(1-2)-+ | |
| | |
?%b-L-Arap4N-(1--P--4)--b-D-GlcpN-(1-6)-a-D-GlcpN
| |
3HOMyr-(1-3)-+ |
|
?%b-L-Arap4N-(1--P--1)--+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14443
|
/Variants 0/-+ 3HOMyr-(1-2)-+
| |
Myr-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
| |
P-4)-+ 3HODco-(1-3)-+
/Variants 0/ is:
3HODco-(1-3)-
OR (exclusively)
?%3HOLau-(1-3)- |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 14449
|
L-gro-a-D-manHepp-(1-2)-+ EtN-(1--P--4)--+
| |
EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-L-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
Trivial name: outer core
Compound class: core oligosaccharide
Reference(s) to other database(s): GTC:G31333NY
- Compound ID: 14450
|
P---P--6)-+ EtN-(1--P--2)--+ Kdop-(2-4)-+
| | |
L-Ala-(1-2)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
P---P--4)-+ |
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Structure type: fragment of a bigger structure
Aglycon: lipid A
Trivial name: outer core
Compound class: core oligosaccharide
- Compound ID: 177
Structure type: homopolymer
Compound class: O-polysaccharide, O-antigen
- Compound ID: 14451
|
R-Lac-(2-4)-+
|
-3)-b-D-ManpNAc-(1-4)-b-D-Glcp6Ac-(1-3)-b-D-FucpNAc4N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, polysaccharide
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